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JPH01246239A - Fluorine-containing carbonyl compound and production thereof - Google Patents

Fluorine-containing carbonyl compound and production thereof

Info

Publication number
JPH01246239A
JPH01246239A JP62294195A JP29419587A JPH01246239A JP H01246239 A JPH01246239 A JP H01246239A JP 62294195 A JP62294195 A JP 62294195A JP 29419587 A JP29419587 A JP 29419587A JP H01246239 A JPH01246239 A JP H01246239A
Authority
JP
Japan
Prior art keywords
fluorine
carbonyl compound
containing carbonyl
formula
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP62294195A
Other languages
Japanese (ja)
Inventor
Tomoya Kitatsume
智哉 北爪
Takashi Yamazaki
孝 山崎
Masasoe Hayashi
正添 林
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Showa Shell Sekiyu KK
Original Assignee
Showa Shell Sekiyu KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Showa Shell Sekiyu KK filed Critical Showa Shell Sekiyu KK
Priority to JP62294195A priority Critical patent/JPH01246239A/en
Priority to US07/221,371 priority patent/US4929760A/en
Publication of JPH01246239A publication Critical patent/JPH01246239A/en
Pending legal-status Critical Current

Links

Classifications

    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

NEW MATERIAL:The fluorine-containing carbonyl compound of formula (R is substituted or unsubstituted lower alkyl, substituted or unsubstituted aromatic group or substituted or unsubstituted arylalkyl). EXAMPLE:3,3,3-Trifluoro-2-hydroxypropyl phenyl ketone. USE:Useful as bioactive substances, pharmaceuticals, agricultural chemicals, organic functional materials, liquid crystals and LB membranes. PREPARATION:The fluorine-containing carbonyl compound of formula I can be produced by reacting a trifluoroaldehyde with a compound of formula II in the presence of lithium diisopropylamine.

Description

【発明の詳細な説明】 皮栗上勿且几立畳 本発明は新規な含フツ素カルボニル化合物とその製造方
法に関するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel fluorine-containing carbonyl compound and a method for producing the same.

これらの新規な含フツ素カルボニル化合物は液晶、生理
活性物質、医薬、農薬(殺菌剤、除草剤、ホルモン剤等
)、有機機能性材料、LB膜等へ利用できる。
These new fluorine-containing carbonyl compounds can be used for liquid crystals, physiologically active substances, medicines, agricultural chemicals (bactericides, herbicides, hormones, etc.), organic functional materials, LB films, and the like.

5 ′ネ\ 、■が”ン しようとする’FWAフッ素
原子をもつ特徴的な性質がもたらず様々な挙動がフッ素
化学の応用範囲を多種多様なものへと展開与させている
5 'ne\, ■ tries to' FWA The characteristic properties of fluorine atoms do not result in various behaviors, and the range of applications of fluorine chemistry has expanded to a wide variety of things.

なかでも、フッ素原子を分子内に組み入れた生理活性物
質の研究は活発に行なわれている。
Among these, research on physiologically active substances incorporating fluorine atoms into their molecules is actively being conducted.

この6M域では、活性発現と分子構造との相関が重要な
課題となるが、非天然産型の有機フン素化合物において
は、炭化水素系の生理活性天然物の分子内の不斉炭素、
特に不斉炭素中にフッ素原子あるいはトリフルオロメチ
ル基を組み入れることは容易ではない。
In this 6M range, the correlation between activity expression and molecular structure is an important issue, but in non-naturally occurring organic fluorine compounds, asymmetric carbon atoms in the molecules of hydrocarbon-based physiologically active natural products,
In particular, it is not easy to incorporate a fluorine atom or a trifluoromethyl group into an asymmetric carbon.

その理由として、フッ素原子が一つでも分子内に導入さ
れると、分子の化学的挙動が大きく変化することが原因
と考えられ、このため通常の有機合成化学で展開されて
いる方法がそのままでは応用できないことがあげられる
The reason for this is thought to be that when even one fluorine atom is introduced into a molecule, the chemical behavior of the molecule changes significantly. There are some things that cannot be applied.

本発明は、分子中にフッ素原子特にトリフルオロメチル
基を含む含フツ素カルボニル化合物およびその合成法を
提供することにある。
The present invention provides a fluorine-containing carbonyl compound containing a fluorine atom, particularly a trifluoromethyl group, in its molecule, and a method for synthesizing the same.

口 占を”ン1するための 本発明は、一般式 (式中Rは置換または未置換低級アルキル基、好ましく
は炭素数10以下のアルキル基、置換又は未置換芳香族
基または置換又は未置換了り5−ルアルキル基である)
で表わされる含フツ素カルボニル化合物を提供するにあ
る。
The present invention for improving the oral numerosity is based on the general formula (wherein R is a substituted or unsubstituted lower alkyl group, preferably an alkyl group having 10 or less carbon atoms, a substituted or unsubstituted aromatic group, or a substituted or unsubstituted aromatic group). 5-rualkyl group)
The present invention provides a fluorine-containing carbonyl compound represented by:

本発明の代表的な化合物のRgは、フェニル基(Ph)
 、フェニルエチル基(C11□C112Ph) 、イ
ソブチル基(C1l zcII (Me) 2 〕、ノ
ルマルヘキシル基((C1lz)sC11+ )などが
ある。
Rg of the representative compound of the present invention is a phenyl group (Ph)
, phenylethyl group (C11□C112Ph), isobutyl group (C1l zcII (Me) 2 ), normal hexyl group ((C1lz)sC11+), and the like.

上記化合物の合成法は次のようである。The method for synthesizing the above compound is as follows.

トリフルオロアルデヒドとRCOCII+(Rは置換ま
たは未置換低級アルキル基、置換又は未置換芳香族基ま
たはアリールアルキル基である)ととリチウムジイソプ
ロピルアミンの存在下で反応させることにより 一般式 (式中Rは上記と同意義である) で表わされる含フツ素カルボニル化合物を得ることにあ
る。
The general formula (wherein R is The purpose of the present invention is to obtain a fluorine-containing carbonyl compound represented by (same meaning as above).

スjU吐上 アルゴン雰囲気下、反応容器に充分に乾燥したテトラヒ
ドロフラン50−およびリチウムジイソプロピルアミン
(56mmo1)を入れ、さらに−50℃に冷却した後
、乾燥テトラヒドロフラン10−に溶かしたアセトフェ
ノン(6,0g、50mtno l! )を加える。
Under an argon atmosphere, sufficiently dried tetrahydrofuran 50- and lithium diisopropylamine (56 mmol) were placed in a reaction vessel, and after further cooling to -50°C, acetophenone (6.0 g, 50 mtno l!).

この反応液を一50°Cに保って30分間攪拌した後、
トリフルオロアセトアルデヒドを吹込み、さらに0℃で
2時間反応させる。
After stirring the reaction solution for 30 minutes while keeping it at -50°C,
Trifluoroacetaldehyde was blown into the mixture, and the mixture was further reacted at 0°C for 2 hours.

反応液に飽和塩化アンモニウム水溶液を加え、生成した
油状物をジエチルエーテルにて抽出し、脱溶媒した後、
粗酸物をシリカゲルクロマトグラフ法により精製して〔
展開液ヘキサン:酢酸エチル−5:1(vo!り)、目
的化合物、(3,3゜3−トリフルオロ−2−ヒドロキ
シ)プロピルフェニルケトンを得た。収率50%。
A saturated aqueous ammonium chloride solution was added to the reaction solution, the resulting oil was extracted with diethyl ether, and the solvent was removed.
The crude acid was purified by silica gel chromatography [
The target compound, (3,3°3-trifluoro-2-hydroxy)propylphenyl ketone, was obtained using a developing solution of hexane:ethyl acetate-5:1 (vo!li). Yield 50%.

得られた化合物の物性は次の如くである。The physical properties of the obtained compound are as follows.

”F NMR(CD(J :l)δ+2.0(d、 J
cr:+−co=7112) ;飄HNMR(CDCl
 3)63.1(C11611a  +dd、JHa−
M++=34112+JMA−cw=7.1Hz)、 
 3.4(CIlaHg、dd+Ju++−cH□14
.111z)+4.1 (OR,br)、4.63 (
CI、a+)、7.43−7.93 (八r−tl):
IR(cm−’)3400(OH)、1685(C−0
)。
”F NMR(CD(J:l)δ+2.0(d, J
cr:+-co=7112) ; 飄HNMR(CDCl
3) 63.1 (C11611a +dd, JHa-
M++=34112+JMA-cw=7.1Hz),
3.4 (CIlaHg, dd+Ju++-cH□14
.. 111z)+4.1 (OR,br), 4.63 (
CI, a+), 7.43-7.93 (8r-tl):
IR (cm-') 3400 (OH), 1685 (C-0
).

次新l建先 実施例1においてアセトフェノン(I’hCOCII:
+)の代りに、 (a)メチルフェニルエチルケトン(r’hc11zc
II□cOclli)、(blメチルイソブチルケトン
((Cll :l) 2CIICII ZCOCI+ 
3 )、(Clメチルn−へキシルケトン(C1l:+
 (Cllz) 5COCII:l)、を用いて実施例
1と同様にして対応する目的化合物 すなわち、 (3,3,3−1−リフルオロ−2−ヒドロキシ)プロ
ピル−フェニルエチルケトン、(3,3,3−ドリフル
オロー2−ヒドロキシ)プロピルイソブチルケトン、お
よび(3,3,3−トリフルオロ−2−ヒドロキシ)プ
ロピル−n−へキシルケトン をそれぞれ得た。収率50%。
In Example 1, acetophenone (I'hCOCII:
+) Instead of (a) methylphenylethyl ketone (r'hc11zc
II□cOclli), (bl methyl isobutyl ketone ((Cll :l) 2CIICII ZCOCI+
3), (Cl methyl n-hexyl ketone (Cl: +
(Cllz) 5COCII:l), the corresponding target compound was prepared in the same manner as in Example 1, namely: (3,3,3-1-lifluoro-2-hydroxy)propyl-phenylethyl ketone, (3,3, 3-Drifluoro-2-hydroxy)propyl isobutyl ketone and (3,3,3-trifluoro-2-hydroxy)propyl-n-hexyl ketone were obtained, respectively. Yield 50%.

これらの目的化合物の物性、”I” 1111+1.’
II N門Rの化学シフトは第1表に示した。
Physical properties of these target compounds, “I” 1111+1. '
The chemical shifts of II N group R are shown in Table 1.

/ / 溌m弧米 本発明により、生理活性物質、医薬、農薬、有機機能性
材料、液晶、LB膜などに利用できる新規な含フツ素カ
ルボニル化合物を合成することができた。
/ / According to the present invention, it was possible to synthesize a novel fluorine-containing carbonyl compound that can be used for physiologically active substances, medicines, agricultural chemicals, organic functional materials, liquid crystals, LB films, etc.

Claims (2)

【特許請求の範囲】[Claims] (1)一般式 ▲数式、化学式、表等があります▼ (式中Rは置換または未置換低級アルキル基、置換又は
未置換芳香族基または置換又は未置換アリールアルキル
基である) で表わされる含フッ素カルボニル化合物。
(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. Fluorine carbonyl compound.
(2)トリフルオロアセトアルデヒドとRCOCH_3
とをリチウムジイソプロピルアミンの存在下で反応させ
ることにより 式 ▲数式、化学式、表等があります▼ (式中Rは置換または未置換低級アルキル基、置換又は
未置換芳香族基または置換又は未置換アリールアルキル
基である) で表わされる化合物を得ることを特徴とする含フッ素カ
ルボニル化合物の製造方法。
(2) Trifluoroacetaldehyde and RCOCH_3
By reacting with lithium diisopropylamine in the presence of lithium diisopropylamine, a formula ▲mathematical formula, chemical formula, table, etc. 1. A method for producing a fluorine-containing carbonyl compound, the method comprising obtaining a compound represented by (which is an alkyl group).
JP62294195A 1987-11-24 1987-11-24 Fluorine-containing carbonyl compound and production thereof Pending JPH01246239A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP62294195A JPH01246239A (en) 1987-11-24 1987-11-24 Fluorine-containing carbonyl compound and production thereof
US07/221,371 US4929760A (en) 1987-11-24 1988-07-19 Fluorine-containing carbonyl compounds and method for preparing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP62294195A JPH01246239A (en) 1987-11-24 1987-11-24 Fluorine-containing carbonyl compound and production thereof

Publications (1)

Publication Number Publication Date
JPH01246239A true JPH01246239A (en) 1989-10-02

Family

ID=17804544

Family Applications (1)

Application Number Title Priority Date Filing Date
JP62294195A Pending JPH01246239A (en) 1987-11-24 1987-11-24 Fluorine-containing carbonyl compound and production thereof

Country Status (1)

Country Link
JP (1) JPH01246239A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6096908A (en) * 1992-01-31 2000-08-01 Kashima Oil Company Optically active fluorinated compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6096908A (en) * 1992-01-31 2000-08-01 Kashima Oil Company Optically active fluorinated compounds

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