JPH01246239A - Fluorine-containing carbonyl compound and production thereof - Google Patents
Fluorine-containing carbonyl compound and production thereofInfo
- 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
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 15
- 239000011737 fluorine Substances 0.000 title claims abstract description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 150000001728 carbonyl compounds Chemical class 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 Fluorine carbonyl compound Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 3
- 239000008204 material by function Substances 0.000 abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000975 bioactive effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements 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
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)
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.
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).
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6096908A (en) * | 1992-01-31 | 2000-08-01 | Kashima Oil Company | Optically active fluorinated compounds |
-
1987
- 1987-11-24 JP JP62294195A patent/JPH01246239A/en active Pending
Cited By (1)
| 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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