JPH01265077A - 2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acid - Google Patents
2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acidInfo
- Publication number
- JPH01265077A JPH01265077A JP9243188A JP9243188A JPH01265077A JP H01265077 A JPH01265077 A JP H01265077A JP 9243188 A JP9243188 A JP 9243188A JP 9243188 A JP9243188 A JP 9243188A JP H01265077 A JPH01265077 A JP H01265077A
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidinyl
- optically active
- allyl
- formula
- benzoic acid
- 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000005711 Benzoic acid Substances 0.000 title claims abstract description 5
- 235000010233 benzoic acid Nutrition 0.000 title claims abstract description 5
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- -1 4-pyrimidinyl-6-fluorophenyl ester Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 6
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005821 Claisen rearrangement reaction Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 25
- 150000002148 esters Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- YVHDMQRVTVCDAS-UHFFFAOYSA-N 2-propylpyrimidine Chemical group CCCC1=NC=CC=N1 YVHDMQRVTVCDAS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、光学活性な、ら旋分子構造を持った化合物及
びそれを含有する液晶化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an optically active compound having a helical molecular structure and a liquid crystal compound containing the same.
液晶表示素子は液晶物質の特性である光学異方性及び誘
電異方性を利用したもので各種の表示方法のものがある
が、そのうち現在最も実用化されているのはねじれネマ
チック型（ＴＮ型）、動的散乱型（ＤＳ型）などである
、しがし最近は他の方式の液晶表示方法の開発も盛んに
行なわれ、中でもコレステリック・ネマチック相転移型
表示及びホワイト・ティラー型カラー表示などがその代
表的なものである。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy, which are the characteristics of liquid crystal materials, and there are various display methods, but the currently most practically used type is the twisted nematic type (TN type). ), dynamic scattering type (DS type), etc. Recently, other types of liquid crystal display methods have been actively developed, including cholesteric-nematic phase transition type display and white-tiller type color display. is a typical example.
これ′らの表示素子に用いられる液晶組成物はいずれも
ネマチック液晶に光学活性物質などを添加して、それぞ
れに適したコレステリックのら旋ピッチをもつ様に調節
される。添加する光学活性物質の分子はねじれた、ら膜
構造をもち、そのら旋ピッチは短かく、かつ熱、光、空
気、水に安定なものが望まれている。The liquid crystal compositions used in these display elements are each adjusted to have an appropriate cholesteric helical pitch by adding an optically active substance to the nematic liquid crystal. It is desired that the molecules of the optically active substance to be added have a twisted, helical membrane structure, have a short helical pitch, and be stable against heat, light, air, and water.
本発明の目的は、以上の様な用途に使用して有用な光学
活性を有し、ねじれた分子構造をもつ新規な化合物を提
供することであり、また以上の様な用途に使用して有用
な本発明の化合物を用いた液晶組成物を提供することで
ある。The purpose of the present invention is to provide a novel compound having optical activity and a twisted molecular structure that is useful for the above-mentioned applications, and to provide a novel compound that is useful for the above-mentioned applications. An object of the present invention is to provide a liquid crystal composition using the compound of the present invention.
本発明は一般式
（上式中Ａは０又は１． ｍは１又は２． Ｒは直
鎖又は枝分れした炭素数１〜１５のアルキル基を示す）
で表わされる光学活性安息香Ｍ２−アリルー４−ピリミ
ジニル−６−フルオロフェニルエステル類およびこれを
含有してなる液晶組成物である。The present invention is based on the general formula (in the above formula, A is 0 or 1. m is 1 or 2. R represents a straight chain or branched alkyl group having 1 to 15 carbon atoms)
These are optically active benzoic M2-allyl-4-pyrimidinyl-6-fluorophenyl esters represented by the formula and a liquid crystal composition containing the same.
本発明の化合物の製造方法の例は、下記反応式によって
示される。An example of the method for producing the compound of the present invention is shown by the following reaction formula.
Ｆ ＣＨ，ＣＨ＝ＣＨ２（上式
中Ｌｍ、Ｒは前記に同じである）すなわち、 １−アリ
ルオキシ−２−フルオロ−４（５−アルキル−２−ピリ
ミジニル）ベンゼンをＮ、 Ｎ−ジエチルアニリン中
加熱することによりクライゼン転位をして、２−アリル
−４（５−アルキル−２−ピリミジニル）−６−フルオ
ロフェノールとＦＪ造した。F CH, CH=CH2 (in the above formula, Lm and R are the same as above), that is, heating 1-allyloxy-2-fluoro-4(5-alkyl-2-pyrimidinyl)benzene in N,N-diethylaniline By doing so, Claisen rearrangement was performed to produce 2-allyl-4(5-alkyl-2-pyrimidinyl)-6-fluorophenol and FJ.
ついで、光学活性安、９、香酸クロリドと２−アリル−
４（５−アルキル−２−ピリミジニル）−６−フルオロ
フェノールをピリジン存在下反応をして目的の光学活性
安息香酸２−アリル４（５−アルキル−２−ピリミジニ
ル）−６−フルオロフェニルエステル類を製造した。Then, optically active ammonium, 9, aromatic acid chloride and 2-allyl-
The desired optically active 2-allyl benzoate 4(5-alkyl-2-pyrimidinyl)-6-fluorophenyl esters are obtained by reacting 4(5-alkyl-2-pyrimidinyl)-6-fluorophenol in the presence of pyridine. Manufactured.
本発明の化合物は、ら旋分子構造をもち、あるものはコ
レステリック・スメクチック液晶を示し、又液晶となら
ないものもあるが、これをネマチック液晶に少量添加し
てコレステリック・ネマチック相転位表示素子素子用又
はホワイト・テーラ−型表示素子用の液晶組成物を得る
ことが出来る。The compounds of the present invention have a helical molecular structure, and some exhibit cholesteric/smectic liquid crystals, while others do not form liquid crystals, but a small amount of this compound is added to nematic liquid crystals for use in cholesteric/nematic phase change display elements. Alternatively, a liquid crystal composition for White-Taylor type display elements can be obtained.
この化合物をネマチック液晶に１％添加して測定して得
られるら族ピッチは２０〜２５μｍ程度である。又、こ
の化合物をＴＮ型表示素子用のネマチック液晶組成物に
添加すると表示面のしま模様（いわゆるリバースドメイ
ン）の発生を少なくして、その性質を改善することが出
来る。The lattice pitch obtained by adding 1% of this compound to a nematic liquid crystal and measuring it is about 20 to 25 μm. Furthermore, when this compound is added to a nematic liquid crystal composition for a TN type display element, it is possible to reduce the occurrence of striped patterns (so-called reverse domains) on the display surface and improve its properties.
以下実施例により本化合物につき更に詳細に説明する。 The present compound will be explained in more detail with reference to Examples below.
実施例１
２−フルオロ−４−（２−（５−プロピル）ピリミジニ
ルクー６−アリルフェノールの製造２−（３−フルオロ
−４−ヒドロキシフェニル）−５−プロピルピリミジン
Ｌｏｇ（０，０４モル）と無水炭酸カリウム８０ｇにア
セトン５００１加えよく攪拌しながら臭化アリルＬｏｇ
（０，０４モル）を加えた。そのまま室温で２時間攪拌
した後に、マントルヒーターで加熱し、還流を４８時間
行った。Example 1 Preparation of 2-fluoro-4-(2-(5-propyl)pyrimidinyl-6-allylphenol) 2-(3-fluoro-4-hydroxyphenyl)-5-propylpyrimidine Log (0.04 mol) Add 5001 acetone to 80 g of anhydrous potassium carbonate and add allyl bromide Log while stirring well.
(0.04 mol) was added. After stirring at room temperature for 2 hours, the mixture was heated with a mantle heater and refluxed for 48 hours.
反応終了後不溶物をｒ別し、アセトン層を減圧留去した
。残った油状物をトルエン溶媒で活性アルミナでカラム
クロマトグラフィーを行った。トルエンを留去し、残っ
た油状物をエタノールで再結晶を行った。このものが２
−（３−フルオロ−４−アリルオキシフェニル）−５−
プロピルピリミジンである。After the reaction was completed, insoluble matter was separated, and the acetone layer was distilled off under reduced pressure. The remaining oil was subjected to column chromatography on activated alumina using toluene as a solvent. Toluene was distilled off, and the remaining oil was recrystallized from ethanol. This one is 2
-(3-fluoro-4-allyloxyphenyl)-5-
It is propylpyrimidine.
このものをＮ、 Ｎ−ジエチルアニリン４０ｍ１に溶
かし、８時間窒素雰囲気下に還流した。放冷後５００ｍ
１の６Ｎ塩酸に反応液を加えた。−晩放置後析出した沈
澱物を炉別し、少量の水でよく洗い、減圧にてよく乾燥
した。このものが２−フルオロ−４−（２−（５−プロ
ピル）ピリミジニル〕−６−アリルフェノールの塩酸塩
である。このものをそのままつぎの反応に用いた。This product was dissolved in 40 ml of N,N-diethylaniline and refluxed under nitrogen atmosphere for 8 hours. 500m after cooling
The reaction solution was added to 6N hydrochloric acid in Step 1. - After standing overnight, the precipitate deposited was filtered out, thoroughly washed with a small amount of water, and thoroughly dried under reduced pressure. This product is 2-fluoro-4-(2-(5-propyl)pyrimidinyl]-6-allylphenol hydrochloride. This product was used as it was in the next reaction.
実施例２
ｓ −（＋） −４−（２−メチルブチル）安息香酸２
−フルオロ−４−（２−（５−プロピル）ピリミジニル
〕−６−アリルフェニルエステル〔１式でｆＪ＝ｏ、
ｍ＝１． Ｒ＝Ｃ３Ｈ７のもの〕の製造Ｓ−（＋）
−４−（２−メチルブチル）安７ａ、香酸クロリド２．
１ｇ（０，０１モル）をピリジン１０−１にとかした
２−フルオロ−４−（２−（５−プロピル）ピリミジニ
ル〕−６−アリルフェノール２７ｇ（０，０１モル）に
加えて室温で攪拌して反応させる。Example 2 s-(+)-4-(2-methylbutyl)benzoic acid 2
-Fluoro-4-(2-(5-propyl)pyrimidinyl)-6-allylphenyl ester [fJ=o in formula 1,
m=1. Production of R=C3H7] S-(+)
-4-(2-methylbutyl)an 7a, aromatic acid chloride 2.
1 g (0.01 mol) was added to 27 g (0.01 mol) of 2-fluoro-4-(2-(5-propyl)pyrimidinyl]-6-allylphenol dissolved in pyridine 10-1, and the mixture was stirred at room temperature. and react.
更にトルエン５０１を加えよく混合して一晩放置してか
ら水１００ｍ１にあけ、 トルエン５０ｍ１を加えて抽
出する。トルエン層を２Ｎ苛性ソーダ水溶液で洗浄した
後、中性になるまで水洗する。Add 501ml of toluene, mix well, leave overnight, pour into 100ml of water, add 50ml of toluene and extract. The toluene layer is washed with a 2N aqueous sodium hydroxide solution and then with water until it becomes neutral.
ついで無水硫酸ナトリウムで乾燥後、トルエンを減圧で
留去し、残った油状物を活性アルミナのカラムを用いて
、トルエン溶媒でクロマト処理を行った溶出したトルエ
ン溶液を減圧にてトルエンを留去し、残った油状物をエ
タノールで再結晶すると目的のＳ−（＋）−４−（２−
メチルブチＪし）安息香酸２−フルオロ−４−（２−（
５−プロピル）ピリミジニル〕フェニルエステルを得た
。After drying over anhydrous sodium sulfate, the toluene was distilled off under reduced pressure, and the remaining oil was chromatographed with a toluene solvent using an activated alumina column.The eluted toluene solution was distilled off toluene under reduced pressure. , the remaining oil is recrystallized with ethanol to obtain the desired S-(+)-4-(2-
Methylbutylbenzoic acid 2-fluoro-4-(2-(
5-propyl)pyrimidinyl]phenyl ester was obtained.
融点７３．３〜７４．９℃、゛ コレステリック−透明
点６．１℃であった。収量２．０ｇ（収率４５％）、こ
のものをメルク社Ｓ−１１３２に１重景％混入して２５
℃で測定したら旋ピッチは２２μｍであった。The melting point was 73.3-74.9°C, and the cholesteric clearing point was 6.1°C. Yield: 2.0g (yield: 45%), this product was mixed with Merck's S-1132 by 1.
The rotational pitch was 22 μm when measured at °C.
実施例３
実施例２におけるＳ−（＋）−４−（２−メチルブチル
）安１口、香酸クロリドの代りにＳ−（＋）−４−＜２
−メチルブチル）ビフェニル−４′−カルボン酸クロリ
ドを用いて種々の光学活性安、ａ、香酸のエステル類を
製造した。Example 3 1 mouth of S-(+)-4-(2-methylbutyl)an in Example 2, S-(+)-4-<2 in place of fragrant chloride
-Methylbutyl)biphenyl-4'-carboxylic acid chloride was used to produce various optically active esters of ammonium, a, and fragrant acid.
Ｓ−（＋）−４−（２−メチルブチル）ビフェニル−４
′−カルボン酸２−フルオロ−４−〔２−（５−プロピ
ル）ピリミジニル〕−６−アリルフェニルエステルＣ−
ｃｈ８０．４〜８１．１℃。S-(+)-4-(2-methylbutyl)biphenyl-4
'-Carboxylic acid 2-fluoro-4-[2-(5-propyl)pyrimidinyl]-6-allylphenyl ester C-
ch80.4-81.1°C.
ｃｈ−１１４０，３℃、このものをメルク社Ｓ−１１３
２に１重量％混入して２５℃で測定したら旋ピッチは２
５μｍであった。ch-1140, 3℃, Merck S-113
When 1% by weight is mixed in 2 and measured at 25℃, the rotational pitch is 2.
It was 5 μm.
応用例
オクタデシル−トリーエトキシシランで垂直配向処理を
したセル厚１０．５μｍのセルに、ＧＲ−６３なる液晶
組成物（チッソ（株）市販品）９０部と本発明実施例３
の３− （＋）−４−（２−メチルブチル）ビフェニル
−４′−カルボン酸２−フルオロ−４−（２−（５−プ
ロピル）ピリミジニルクー６−アリルフェニルエステル
１０部からなる液晶組成物を密封することによりコレス
テリック−ネマチック相転位表示素子が得られ、その作
動しきい値電圧は１２．ＯＶであった。Application Example 90 parts of a liquid crystal composition called GR-63 (commercially available from Chisso Corporation) and Example 3 of the present invention were placed in a cell having a cell thickness of 10.5 μm that had been vertically aligned with octadecyl-triethoxysilane.
A liquid crystal composition consisting of 10 parts of 3-(+)-4-(2-methylbutyl)biphenyl-4'-carboxylic acid 2-fluoro-4-(2-(5-propyl)pyrimidinyl-6-allylphenyl ester) By sealing, a cholesteric-nematic phase change display element was obtained, the operating threshold voltage of which was 12.OV.
応用例２
市販のＴＮ用液晶組成物Ｓ−１１３２（メルク社製フェ
ニルシクロヘキサン系液晶組成物）９９部に本発明実施
例２で製造したＳ−（＋） −（２−メチルブチル）安
息香酸２−フルオロ−４−（２−（５−プロピル）ピリ
ミジニルシー６−アリルフェニルエステル１部を加えた
液晶組成物を使用したＴＮセルは、この化合物を添加し
ないで製造したＴＮセルに比較してリバースメインが大
幅に減少していることが肉眼により観察された。Application Example 2 S-(+)-(2-methylbutyl)benzoic acid 2- produced in Example 2 of the present invention was added to 99 parts of a commercially available liquid crystal composition for TN S-1132 (phenylcyclohexane liquid crystal composition manufactured by Merck & Co., Ltd.). A TN cell using a liquid crystal composition to which 1 part of fluoro-4-(2-(5-propyl)pyrimidinylcy-6-allylphenyl ester is added has a reverse main content compared to a TN cell manufactured without the addition of this compound. It was observed with the naked eye that there was a significant decrease in
以上that's all
Claims (1)
分れした炭素数１〜１５のアルキル基を示す）で表わさ
れる光学活性安息香酸の２−アリル−４−ピリミジニル
−６−フルオロフェニルエステル類。 ２）第１請求項記載の光学活性安息香酸の２−アリル−
４−ピリミジニル−６−フルオロフェニルエステル類を
少なくとも一種類含有する液晶組成物。[Claims] 1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼... (I) (In the above formula, l is 0 or 1, m is 1 or 2, R is a straight chain or branched 2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acid represented by (representing a separated alkyl group having 1 to 15 carbon atoms). 2) 2-allyl of optically active benzoic acid according to claim 1
A liquid crystal composition containing at least one 4-pyrimidinyl-6-fluorophenyl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9243188A JPH01265077A (en) | 1988-04-14 | 1988-04-14 | 2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9243188A JPH01265077A (en) | 1988-04-14 | 1988-04-14 | 2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01265077A true JPH01265077A (en) | 1989-10-23 |
Family
ID=14054250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9243188A Pending JPH01265077A (en) | 1988-04-14 | 1988-04-14 | 2-allyl-4-pyrimidinyl-6-fluorophenyl esters of optically active benzoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01265077A (en) |
-
1988
- 1988-04-14 JP JP9243188A patent/JPH01265077A/en active Pending
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