NO134371B - - Google Patents
Download PDFInfo
- Publication number
- NO134371B NO134371B NO2098/72A NO209872A NO134371B NO 134371 B NO134371 B NO 134371B NO 2098/72 A NO2098/72 A NO 2098/72A NO 209872 A NO209872 A NO 209872A NO 134371 B NO134371 B NO 134371B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- water
- recovered
- reaction mixture
- dione
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- HXZILEQYFQYQCE-UHFFFAOYSA-N 2-methylcyclopentane-1,3-dione Chemical compound CC1C(=O)CCC1=O HXZILEQYFQYQCE-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- -1 m-methoxybenzyl Chemical group 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- YDFBIBUYOUFJMR-UHFFFAOYSA-N 2-ethylcyclopentane-1,3-dione Chemical compound CCC1C(=O)CCC1=O YDFBIBUYOUFJMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WRKGBXKSAFJPMA-UHFFFAOYSA-N 2-ethyl-2-(3-oxobutyl)cyclopentane-1,3-dione Chemical compound CC(=O)CCC1(CC)C(=O)CCC1=O WRKGBXKSAFJPMA-UHFFFAOYSA-N 0.000 description 2
- ZNVNGGMKNCURSF-UHFFFAOYSA-N 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound CC(=O)CCC1(C)C(=O)CCCC1=O ZNVNGGMKNCURSF-UHFFFAOYSA-N 0.000 description 2
- OZBYSCPBJGAYMQ-UHFFFAOYSA-N 2-methyl-2-(3-oxobutyl)cyclopentane-1,3-dione Chemical compound CC(=O)CCC1(C)C(=O)CCC1=O OZBYSCPBJGAYMQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RFCLQVSOHWJXEU-UHFFFAOYSA-N 2-[6-(3-methoxyphenyl)-3-oxohexyl]-2-methylcyclopentane-1,3-dione Chemical compound COC1=CC=CC(CCCC(=O)CCC2(C)C(CCC2=O)=O)=C1 RFCLQVSOHWJXEU-UHFFFAOYSA-N 0.000 description 1
- ZQYLUOYVHHWICM-UHFFFAOYSA-N 2-butyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound C(CCC)C1(C(CCCC1=O)=O)CCC(C)=O ZQYLUOYVHHWICM-UHFFFAOYSA-N 0.000 description 1
- YMQRPZZAFLGYQY-UHFFFAOYSA-N 2-butylcyclohexane-1,3-dione Chemical compound CCCCC1C(=O)CCCC1=O YMQRPZZAFLGYQY-UHFFFAOYSA-N 0.000 description 1
- JTRQSSRXYULBAA-UHFFFAOYSA-N 2-ethyl-2-(3-oxobutyl)cyclohexane-1,3-dione Chemical compound CC(=O)CCC1(CC)C(=O)CCCC1=O JTRQSSRXYULBAA-UHFFFAOYSA-N 0.000 description 1
- CBYSZLTXXOKQQO-UHFFFAOYSA-N 2-ethylcyclohexane-1,3-dione Chemical compound CCC1C(=O)CCCC1=O CBYSZLTXXOKQQO-UHFFFAOYSA-N 0.000 description 1
- QDQKCEIOMJUGKJ-UHFFFAOYSA-N 2-methyl-2-(3-oxopentyl)cyclopentane-1,3-dione Chemical compound CCC(=O)CCC1(C)C(=O)CCC1=O QDQKCEIOMJUGKJ-UHFFFAOYSA-N 0.000 description 1
- VSGJHHIAMHUZKF-UHFFFAOYSA-N 2-methylcyclohexane-1,3-dione Chemical compound CC1C(=O)CCCC1=O VSGJHHIAMHUZKF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NHMJKYVPXYBHSL-UHFFFAOYSA-N 3-hydroxy-2-methylcyclohex-2-en-1-one Chemical compound CC1=C(O)CCCC1=O NHMJKYVPXYBHSL-UHFFFAOYSA-N 0.000 description 1
- QREBEZZOILCJEP-UHFFFAOYSA-N 6-(3-methoxyphenyl)hex-1-en-3-one Chemical compound COC1=CC=CC(CCCC(=O)C=C)=C1 QREBEZZOILCJEP-UHFFFAOYSA-N 0.000 description 1
- 239000012027 Collins reagent Substances 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- NKRNGKIEDAVMHL-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1 NKRNGKIEDAVMHL-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005837 enolization reaction Methods 0.000 description 1
- MGPSIDGTLFKDEY-UHFFFAOYSA-N ethyl 5-oxohexanoate Chemical compound CCOC(=O)CCCC(C)=O MGPSIDGTLFKDEY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IMTFKLOKSJDBIM-UHFFFAOYSA-N methyl 7-(1-methyl-2,5-dioxocyclopentyl)-5-oxoheptanoate Chemical compound COC(=O)CCCC(=O)CCC1(C)C(=O)CCC1=O IMTFKLOKSJDBIM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/487—Saturated compounds containing a keto group being part of a ring containing hydroxy groups
- C07C49/507—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic
- C07C49/513—Saturated compounds containing a keto group being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US476270A | 1970-01-21 | 1970-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134371B true NO134371B (xx) | 1976-06-21 |
| NO134371C NO134371C (xx) | 1976-09-29 |
Family
ID=27421984
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO200/71A NO134983C (xx) | 1970-01-21 | 1971-01-20 | |
| NO2099/72A NO138000C (no) | 1970-01-21 | 1972-06-13 | Fremgangsmaate for fremstilling av 19-nortestosteron og 19-nor-9beta, 10alfa-testosteron henholdsvis 17beta-tert.-butyleter derav |
| NO2098/72A NO134371C (xx) | 1970-01-21 | 1972-06-13 | |
| NO761104A NO761104L (xx) | 1970-01-21 | 1976-03-30 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO200/71A NO134983C (xx) | 1970-01-21 | 1971-01-20 | |
| NO2099/72A NO138000C (no) | 1970-01-21 | 1972-06-13 | Fremgangsmaate for fremstilling av 19-nortestosteron og 19-nor-9beta, 10alfa-testosteron henholdsvis 17beta-tert.-butyleter derav |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO761104A NO761104L (xx) | 1970-01-21 | 1976-03-30 |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US3975440A (xx) |
| JP (2) | JPS5737573B1 (xx) |
| AT (4) | AT308087B (xx) |
| BE (1) | BE761783A (xx) |
| CA (2) | CA993878A (xx) |
| CH (3) | CH588434A5 (xx) |
| DE (3) | DE2102623C2 (xx) |
| DK (2) | DK146717C (xx) |
| ES (2) | ES387449A1 (xx) |
| FI (2) | FI53450C (xx) |
| FR (2) | FR2077253B1 (xx) |
| GB (2) | GB1325632A (xx) |
| HU (2) | HU166419B (xx) |
| IE (3) | IE35093B1 (xx) |
| IL (1) | IL35985A (xx) |
| NL (2) | NL164267C (xx) |
| NO (4) | NO134983C (xx) |
| PH (2) | PH12661A (xx) |
| SE (2) | SE393798B (xx) |
| YU (1) | YU35332B (xx) |
| ZA (1) | ZA7120B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201869A (en) * | 1970-12-21 | 1980-05-06 | Hoffmann-La Roche Inc. | Intermediates for steroid total synthesis process utilizing asymmetric induction |
| ZA814972B (en) * | 1980-07-30 | 1982-07-28 | Beecham Group Plc | Reduced naphthalenes,their preparation and use |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2668858A (en) * | 1954-02-09 | Process for their preparation | ||
| US2407673A (en) * | 1941-06-20 | 1946-09-17 | Research Corp | Process for the synthesis of 1-keto-8-methylhexahydroindanol-1 |
| US2833694A (en) * | 1955-08-25 | 1958-05-06 | Ciba Pharm Prod Inc | Process for splitting racemates |
| NL130309C (xx) * | 1963-11-29 | |||
| NL131552C (xx) * | 1965-04-28 | |||
| AT278767B (de) * | 1965-10-13 | 1970-02-10 | Hoffmann La Roche | Verfahren zur herstellung von neuen indanderivaten |
| US3501479A (en) * | 1967-05-19 | 1970-03-17 | American Cyanamid Co | Dihydroquinolines and substituted dihydroquinolines and method of preparing the same |
| US3897460A (en) * | 1968-10-04 | 1975-07-29 | Hoffmann La Roche | 3{62 -Tertiarybutoxy-decahydro-benz{8 E{9 indenes |
| DE2016750A1 (de) * | 1970-04-04 | 1971-10-14 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von 2,2 disubstituierten Cycloalkan 1,3 dionen |
-
1970
- 1970-12-09 US US05/096,597 patent/US3975440A/en not_active Expired - Lifetime
-
1971
- 1971-01-04 ZA ZA710020A patent/ZA7120B/xx unknown
- 1971-01-07 CH CH18571A patent/CH588434A5/xx not_active IP Right Cessation
- 1971-01-07 CH CH638775A patent/CH597129A5/xx not_active IP Right Cessation
- 1971-01-10 PH PH12122A patent/PH12661A/en unknown
- 1971-01-12 IL IL35985A patent/IL35985A/xx unknown
- 1971-01-14 IE IE42/71A patent/IE35093B1/xx unknown
- 1971-01-14 IE IE1797/73A patent/IE35095B1/xx unknown
- 1971-01-14 IE IE1796/73A patent/IE35094B1/xx unknown
- 1971-01-19 YU YU117/71A patent/YU35332B/xx unknown
- 1971-01-19 GB GB4688172A patent/GB1325632A/en not_active Expired
- 1971-01-19 GB GB257171A patent/GB1325631A/en not_active Expired
- 1971-01-20 AT AT45571A patent/AT308087B/de active
- 1971-01-20 FI FI152/71A patent/FI53450C/fi active
- 1971-01-20 AT AT392372A patent/AT316533B/de not_active IP Right Cessation
- 1971-01-20 NO NO200/71A patent/NO134983C/no unknown
- 1971-01-20 DE DE2102623A patent/DE2102623C2/de not_active Expired
- 1971-01-20 AT AT392272A patent/AT315142B/de not_active IP Right Cessation
- 1971-01-20 ES ES387449A patent/ES387449A1/es not_active Expired
- 1971-01-20 FR FR717101825A patent/FR2077253B1/fr not_active Expired
- 1971-01-20 DE DE2166994A patent/DE2166994C3/de not_active Expired
- 1971-01-20 BE BE761783A patent/BE761783A/xx not_active IP Right Cessation
- 1971-01-20 DE DE19712166993 patent/DE2166993A1/de active Pending
- 1971-01-21 JP JP177971A patent/JPS5737573B1/ja active Pending
- 1971-01-21 HU HUHO1647A patent/HU166419B/hu unknown
- 1971-01-21 DK DK25571A patent/DK146717C/da not_active IP Right Cessation
- 1971-01-21 CA CA103,278A patent/CA993878A/en not_active Expired
- 1971-01-21 NL NL7100813.A patent/NL164267C/xx not_active IP Right Cessation
- 1971-01-21 HU HUHO1349A patent/HU166411B/hu unknown
- 1971-01-21 SE SE7100704A patent/SE393798B/xx unknown
- 1971-09-08 ES ES394882A patent/ES394882A1/es not_active Expired
- 1971-11-05 FR FR717139725A patent/FR2112170B1/fr not_active Expired
-
1972
- 1972-05-05 AT AT392472A patent/AT348150B/de not_active IP Right Cessation
- 1972-06-13 NO NO2099/72A patent/NO138000C/no unknown
- 1972-06-13 NO NO2098/72A patent/NO134371C/no unknown
-
1973
- 1973-12-28 SE SE7317592A patent/SE404607B/xx unknown
-
1975
- 1975-08-04 PH PH17445A patent/PH11206A/en unknown
-
1976
- 1976-01-07 CH CH1535676A patent/CH589024A5/xx not_active IP Right Cessation
- 1976-03-04 CA CA247,076A patent/CA1013752A/en not_active Expired
- 1976-03-30 NO NO761104A patent/NO761104L/no unknown
-
1977
- 1977-05-23 FI FI771632A patent/FI771632A/fi not_active Application Discontinuation
- 1977-11-11 JP JP13556877A patent/JPS5373541A/ja active Granted
-
1978
- 1978-06-12 US US05/914,840 patent/US4189447A/en not_active Expired - Lifetime
-
1979
- 1979-07-16 DK DK298479A patent/DK298479A/da not_active Application Discontinuation
- 1979-10-02 NL NL7907334A patent/NL7907334A/nl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kingsbury et al. | Studies in Stereochemistry. XXXII. Mechanism of Elimination of Sulfoxides1 | |
| Cram et al. | Macro Rings. XIII. Synthesis and Properties of 1, 7-Cyclododecadiyne and Related Compounds1 | |
| Windholz et al. | Total synthesis of 19-norsteroids. I. d, l-Estrone methyl ether | |
| US3029287A (en) | Preparation of unsaturated ketones | |
| Akhtar et al. | Some Radical Exchange Reactions during Nitrite Ester Photolysis1 | |
| Gardner | Organic Peracid Oxidation of Some Enol Esters Involving Rearrangement1 | |
| US4161480A (en) | Intermediates for the synthesis of 4-demethoxydaunorubicin | |
| US3941828A (en) | Process for the preparation of cyclic ketones | |
| Krubiner et al. | Studies in the 21-methyl steroid series. Organoborane rearrangements and a novel synthesis of 21-methyl-19-norsteroids | |
| NO134371B (xx) | ||
| US3954794A (en) | Heterocyclic compounds | |
| US3816536A (en) | 2-2-disubstituted cycloalkane-1,3-diones | |
| Jacobs et al. | A-Nor-Δ3 (5)-cholesten-2-one1 | |
| Tarbell et al. | A Rearrangement Involving Aromatization. The Condensation of Δ4-Tetrahydrophthalaldehyde with Diethyl Acetonedicarboxylate1 | |
| US4124642A (en) | 6,6,7-Trimethyl-tricyclo[5.2.2.01,5 ]undec-8-en-2-one | |
| Elks | Studies in the synthesis of cortisone. Part VI. Conjugated trienones derived from ergosterol | |
| US3975442A (en) | 2-Alkyl-2-(3-oxoalkyl)-1,3-cyclopentadiones | |
| Goldblum et al. | Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangement | |
| Suzuki | Studies on Fluorene Derivatives. XV. The Clemmensen Reduction of Fluorenone | |
| US3712928A (en) | Phenylcyclohexane derivatives and methods for their manufacture | |
| DRAKE et al. | A new synthesis of picene | |
| US4110380A (en) | Asymmetric synthesis of organic compounds | |
| Suginome et al. | Photoinduced molecular transformations. Part 98. The photochemistry of steroidal 6-membered cyclic. ALPHA.-nitro ketones. | |
| Peet et al. | Photochemical and acid-catalyzed rearrangements of tricyclo [4.4. 2.0] dodecanones | |
| Vingiello et al. | 7-Phenyldibenz [a, h] anthracene and Benzo [e] naphtho [1, 2-b] pyrene1, 2 |