JPH04187676A - Optically active compound and liquid crystal composition containing the same - Google Patents
Optically active compound and liquid crystal composition containing the sameInfo
- Publication number
- JPH04187676A JPH04187676A JP31644890A JP31644890A JPH04187676A JP H04187676 A JPH04187676 A JP H04187676A JP 31644890 A JP31644890 A JP 31644890A JP 31644890 A JP31644890 A JP 31644890A JP H04187676 A JPH04187676 A JP H04187676A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- expressed
- optically active
- pyridine
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 28
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 9
- -1 formic acid ester Chemical class 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract description 6
- 150000008062 acetophenones Chemical class 0.000 abstract description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 3
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007818 Grignard reagent Substances 0.000 abstract description 2
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- 150000004795 grignard reagents Chemical class 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical class N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は強誘電性液晶材料として有用な新規な光学活性
化合物及びそれを含有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel optically active compound useful as a ferroelectric liquid crystal material and a liquid crystal composition containing the same.
（従来の技術）
液晶表示素子の表示方式として現在：〈実用化されてい
る代表的なものとしてねじれネマチック（ＴＮ）型があ
る。しかしながらネマチック液晶相を利用するこの方式
では、ＣＲＴなどの表示方式と比較して応答速度が遅い
、視野角特性に劣る等の問題がありデイスプレィとして
の用途は限定されていた。(Prior Art) Current display methods for liquid crystal display devices include: A twisted nematic (TN) type is currently in use. However, this system using a nematic liquid crystal phase has problems such as slow response speed and inferior viewing angle characteristics compared to display systems such as CRT, and its use as a display has been limited.
最近、クラーク及びラガウェルらにより強誘電性液晶を
用いる表示方式が報告されている（特開昭５６−１０７
２１６号、米国特許第４３６７９２４号等）が、これに
よると強誘電性液晶は高速応答やメモリー性のある双安
定状態を比現さゼることが可能であり、また視野角特性
も優れるなどの点から次世代の液晶表示素子として江目
を集めている。Recently, a display system using ferroelectric liquid crystal has been reported by Clark and Lageruer et al.
216, U.S. Patent No. 4,367,924, etc.), ferroelectric liquid crystals can exhibit high-speed response and a bistable state with memory properties, and also have excellent viewing angle characteristics. Since then, it has been attracting attention as a next-generation liquid crystal display element.
強誘電性液晶の液晶相のひとつとして、カイラルスメク
チックＣ（以下、Ｓｃ”と省略する。）相がある。表示
素子として用いるだめには、輻広いＳｃ”相を有し高速
応答すること等、多くの特性が要求されるが単一化合物
でこれらを満足するものはなく、数種の化合物から成る
液晶組成物で対応しているのが現状である。その組成物
の構成方法のひとつとして強誘電性を示さないスメクチ
ックＣ（以下、Ｓｃと省略する。）相を示す液晶化合物
もしくは液晶組成物（以下、ヘース液晶という。）に光
学活性化合物を添加する方法がある（Ｍｏ１．Ｃｒｙｓ
ｔ、Ｌｉｑ、Ｃｒｙｓｆ、、８９．３２７ （１９８２
））。One of the liquid crystal phases of ferroelectric liquid crystal is the chiral smectic C (hereinafter abbreviated as Sc) phase.If it is to be used as a display element, it must have a wide Sc'' phase and a high-speed response. Although many properties are required, there is no single compound that satisfies them, and currently liquid crystal compositions consisting of several types of compounds are used. One method for constructing the composition is to add an optically active compound to a liquid crystal compound or liquid crystal composition (hereinafter referred to as Hess liquid crystal) that exhibits a smectic C (hereinafter abbreviated as Sc) phase that does not exhibit ferroelectricity. There is a method (Mo1.Crys
t, Liq, Crysf, 89.327 (1982
)).
光学活性な化合物は強誘電性液晶組成物の成分として使
用したとき、その組成物の自発分極を発現させる役割を
担うものであり、新規な光学活性化合物の開発が望まれ
ていた。When an optically active compound is used as a component of a ferroelectric liquid crystal composition, it plays a role in causing the composition to exhibit spontaneous polarization, and the development of a new optically active compound has been desired.
（発明の目的）
本発明の目的は、強誘電性液晶組成物の成分として有用
な新規な光学活性化合物及び液晶組成物を提供すること
にある。(Object of the Invention) An object of the present invention is to provide a novel optically active compound and a liquid crystal composition useful as components of a ferroelectric liquid crystal composition.
（問題点を解決するための手段）
本発明の目的は、一般式（１）
〔（１）式中、Ｒは炭素数１〜１０のアルキル基若しく
はアルコキシ基を表し、Ｒｏは光学活性基、ｘ’ 、ｘ
’ はそれぞれ独立に水素原子、ハロゲン原子又はシア
ノ基、ｎは１又は２を表す。〕で表される光学活性化合
物、及び一般式（１）の化合物の少なくとも１種類以上
を含有することを特徴とする液晶組成物を開発する事に
より解決された。(Means for Solving the Problems) The object of the present invention is to provide a compound of the general formula (1) [wherein R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms, Ro represents an optically active group, x', x
' each independently represents a hydrogen atom, a halogen atom or a cyano group, and n represents 1 or 2. ] The problem was solved by developing a liquid crystal composition characterized by containing at least one of the optically active compound represented by the formula (1) and the compound represented by the general formula (1).
本発明の化合物は、例えば以下の様なルートで製造でき
る。The compound of the present invention can be produced, for example, by the following route.
〔（１）式中、Ｒは炭素数１〜１０のアル牛ル基もしく
はアルコキシ基を表し、Ｒｏは光学活性基、ｘ’ 、ｘ
’ はそれぞれ独立に水素原子、ハロゲン原子又はシア
ノ基、ｎは１又は２を表す。〕即ち、置換アセトフェノ
ン（１）とぎ酸エステル（２）とをナトリウムメトキサ
イド存在下に反応させてエルレートとし、さらにこれを
シアノアセトアミドと反応させる事によりピリドン体（
３）とする。次いでこれをオキシ塩化リンと反応させて
クロル体（４）とした後、脱クロル化してシアン体（５
）とする。このシアン体（５）とグリニヤール試薬とを
反応させる事により、（Ｉ）の化合物を製造できる。[In the formula (1), R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms, Ro is an optically active group, x', x
' each independently represents a hydrogen atom, a halogen atom or a cyano group, and n represents 1 or 2. ] That is, substituted acetophenone (1) and formic acid ester (2) are reacted in the presence of sodium methoxide to form erulate, which is further reacted with cyanoacetamide to form pyridone (
3). Next, this was reacted with phosphorus oxychloride to form the chloride (4), and then dechlorinated to form the cyanide (5).
). Compound (I) can be produced by reacting this cyanogen body (5) with a Grignard reagent.
本発明の化合物として、例えば以下に示すような化合物
を挙げることができる。Examples of the compounds of the present invention include the following compounds.
５−（（３Ｓ）−３−メチルペンタノイル）−２−（４
−へキシルオキシフェニル）ピリジン５−（（３Ｓ）−
３−メチルペンタノイル）−２−（４−へブチルフェニ
ル）ピリジン５−（（３Ｓ）−３−メチルペンタノイル
）−２−（４−へキシルヒフェニル−４゛ −）ピリジ
ン
５−（（３Ｓ）−３−メチルペンタノイル）−２−（４
−へブチルビフェニル−４゛ −）ピリジン
５− （（３ｓ）−３−メチルペンタノイル）−一（４
−才クチル−２−フルオロフェニル）ビジン
５−（（３Ｓ）−３−メチルペンタノイル）−２−（４
−オクチルオキシ−３−シアノフェニル）ピリジン
５−（（３Ｓ）−３−メチルペンタノイル）−２−（４
−ノニル−２，３−ジフルオロフェニル）ピリジン
５−（（３Ｓ）−３−フルオロノナノイル）−２−（４
−へキシルオキシフェニル）ピリジン５− （（３Ｓ）
−３−フルオロノナノイル）−２−（４−へブチルフェ
ニル）ピリジン５− （（３Ｓ）−３−フルオロノナノ
イル）−２−（４−オクチルフェニル）ピリジン５−
（（３Ｓ）−３−フルオロノナノイル）−２−（４−へ
キシルビフェニル−４′−）ピリジン
５− （（３Ｓ）−３−フルオロノナノイル）−２−（
４−へブチルビフェニル−４°−）ピリジン
５− （（３Ｓ）−３−フルオロ−（４Ｓ）−４−メチ
ルヘキサノイル）−１−（４−へキシルフェニル）ピリ
ジン
５− （（３Ｓ）−３−フルオロ−（４Ｓ）−４−メチ
ルヘキサノイル）−２−（４−ヘキシルビフェニル−４
゛−）ピリジン
５− （（３Ｓ）−３−フルオロ−５−メチルヘキサノ
イル）−２−（４−へ牛シルフェニルンピリジン
５−（（３Ｓ）−３−フルオｏ−５−メチルヘキサノイ
ル）−２−（４−へキシルビフェニル−４“ −）ピリ
ジン
５− （（３Ｓ）−３−フルオロ−４−メチルヘプタノ
イル）−２−（４−へ牛シルフェニル）ピリジン
５−（（３Ｓ）−３−フルオｏ−４−メチルヘプタノイ
ル）−２−（４−へキシルビフェニル＝４゛−）ピリジ
ン
また本発明の光学活性化合物と併せて用いられるベース
液晶の成分としては、フェニルヘンシェード系、シッフ
塩基系、ビフェニル系、フェニルピリミジン系、フェニ
ルピリジン系等の液晶化合物が挙げられる。5-((3S)-3-methylpentanoyl)-2-(4
-hexyloxyphenyl)pyridine 5-((3S)-
3-Methylpentanoyl)-2-(4-hebutylphenyl)pyridine 5-((3S)-3-methylpentanoyl)-2-(4-hexylhyphenyl-4'-)pyridine 5-(( 3S)-3-methylpentanoyl)-2-(4
-hebutylbiphenyl-4'-)pyridine5- ((3s)-3-methylpentanoyl)-1(4
-Ctyl-2-fluorophenyl)bidine 5-((3S)-3-methylpentanoyl)-2-(4
-octyloxy-3-cyanophenyl)pyridine 5-((3S)-3-methylpentanoyl)-2-(4
-nonyl-2,3-difluorophenyl)pyridine 5-((3S)-3-fluorononanoyl)-2-(4
-hexyloxyphenyl)pyridine 5- ((3S)
-3-fluorononanoyl)-2-(4-hebutylphenyl)pyridine 5- ((3S)-3-fluorononanoyl)-2-(4-octylphenyl)pyridine 5-
((3S)-3-fluorononanoyl)-2-(4-hexylbiphenyl-4'-)pyridine5- ((3S)-3-fluorononanoyl)-2-(
4-Hebutylbiphenyl-4°-)pyridine 5- ((3S)-3-fluoro-(4S)-4-methylhexanoyl)-1-(4-hexylphenyl)pyridine 5- ((3S)- 3-Fluoro-(4S)-4-methylhexanoyl)-2-(4-hexylbiphenyl-4
゛-)Pyridine 5-((3S)-3-fluoro-5-methylhexanoyl)-2-(4- to bovine sylphenylumpyridine 5-((3S)-3-fluoro-5-methylhexanoyl )-2-(4-hexylbiphenyl-4"-)pyridine5-((3S)-3-fluoro-4-methylheptanoyl)-2-(4-hexylbiphenyl)pyridine5-((3S) -3-fluoro-4-methylheptanoyl)-2-(4-hexylbiphenyl=4゛-)pyridine Also, as a component of the base liquid crystal used in conjunction with the optically active compound of the present invention, phenylhenshade type , Schiff base-based, biphenyl-based, phenylpyrimidine-based, and phenylpyridine-based liquid crystal compounds.
（実施例）
以下に実施例を示すが本発明はこれに限定されるもので
はない。(Example) Examples are shown below, but the present invention is not limited thereto.
実施例１゜
５− （（３Ｓ）−３−メチルペンタノイル）−２−（
４−へブチルフェニル）ピリジン（（１）式において、
Ｒ＝ｎ−ＣＨＨａｔ、Ｒ’ ＝ＣＨＨｔ ＣＨ（ＣＨ，
）ＣＨ，−１Ｘ’ 、Ｘ’ ＝Ｈ，ｎ＝１のもの）
（１）５−シアノ−２−（４−へブチルフェニル）ピリ
ドンの製造
ナトリウムメトキサイド５９．４ｇ （１モル）トルエ
ン３Ｉの溶液に、４−へブチルアセトフェノン２１８ｃ
＋（１モル）、ギ酸エチル７８９（１゜０５モル）を滴
下後、室温で８時間攪拌した。反応溶液に、ｎ−ブタノ
ール５００ｍ１．水１１を加えて水層を取り比し、α−
シアノアセトアミド８４９（１モル）、酢酸ピペリジン
（酢酸８ｍｌ十ピペリジン１４ｍ１／水５０ｍ１）を加
え、９０°Ｃで２時間攪拌した。６０°Ｃまで冷却後。Example 1゜5-((3S)-3-methylpentanoyl)-2-(
4-hebutylphenyl)pyridine (in formula (1),
R=n-CHHat, R'=CHHt CH(CH,
) CH, -1X', Add 4-hebutylacetophenone 218c to the solution.
After dropping 789 (1.05 mol) of ethyl formate and 789 (1.05 mol) of ethyl formate, the mixture was stirred at room temperature for 8 hours. Add 500 ml of n-butanol to the reaction solution. Add water 11, remove the aqueous layer, and α-
Cyanoacetamide 849 (1 mol) and piperidine acetate (8 ml acetic acid, 14 ml 10 piperidine/50 ml water) were added, and the mixture was stirred at 90°C for 2 hours. After cooling to 60°C.
酢酸を加えて析出した結晶を濾別し、メタノールで洗浄
後、乾燥し、５−シアノ−２−（４−へブチルフェニル
）ピリドン１５３９ （５２％）を得た。Crystals precipitated by adding acetic acid were filtered, washed with methanol, and dried to obtain 5-cyano-2-(4-hebutylphenyl)pyridone 1539 (52%).
（２）５−シアノ−２−（４−へブチルフェニル）ピリ
ジンの製造
５−シアノ−２−（４−へブチルフェニル）ピリドン１
，５３９（０，５２モル）、オキシ塩化リン２９０ｍ１
（３，１２モル）の溶液を２０時間加熱還流した。(2) Production of 5-cyano-2-(4-hebutylphenyl)pyridine 5-cyano-2-(4-hebutylphenyl)pyridone 1
,539 (0.52 mol), phosphorus oxychloride 290 ml
(3.12 mol) was heated under reflux for 20 hours.
反応液を水にあけ、水酸化ナトリウム水溶液によりアル
カリ性とした後、析出した結晶を濾別した。この粗結晶
を、カラムクロマトグラフィー、再結晶により精製して
、５−シアノ−６−りｏｏ−２−（４−へブチルフェニ
ル）ピリジン１２４９（７７％）を得た。次いでこのク
ロル体１００９（０，３２モル）、ジメチルホルムアミ
ド１．５１の溶液に、亜鉛粉末６３９ （０゜９６モル
）、ヨウ化ナトリウム７２９（０，４８モル）、水８．
６ｇ （０，４８モル）を加え、１３０°Ｃで５時間攪
拌した。反応溶液を濾過し。The reaction solution was poured into water and made alkaline with an aqueous sodium hydroxide solution, and then the precipitated crystals were filtered off. The crude crystals were purified by column chromatography and recrystallization to obtain 5-cyano-6-rioo-2-(4-hebutylphenyl)pyridine 1249 (77%). Next, to a solution of this chloride 1009 (0.32 mol) and dimethylformamide 1.51, zinc powder 639 (0.96 mol), sodium iodide 729 (0.48 mol), and water 8.
6g (0.48 mol) was added and stirred at 130°C for 5 hours. Filter the reaction solution.
濾液に酢酸を加えトルエンで抽出して溶媒留去後。Acetic acid was added to the filtrate, extracted with toluene, and the solvent was distilled off.
残量をカラムクロマトグラフィー、再結晶により精製し
て、５−シアノ−２−（４−へブチルフェニル）ピリジ
ン５２．５９ （５９％）を得た。The remaining amount was purified by column chromatography and recrystallization to obtain 52.59 (59%) of 5-cyano-2-(4-hebutylphenyl)pyridine.
（３）５− （（３Ｓ）−３−メチルペンタノイル−２
−（４−へブチルフェニル）ピリジンの製造
金属マグネシウム０．８９ｇ （０，０３６モル）を含
むテトラヒドロフラン溶液１０ｍ１に１−ブロモ−（２
Ｓ）−２−メチルブタン５．０９（０，０３３モル）の
テトラヒドロフラン溶液４０ｍ１を２５−３０”Ｃで滴
下し、グリニ＋−ル試藁をＩＩ製した。この溶液に５−
シアノ−２−（４−へブチルフェニル）ピリジン５．１
７（］（００，０１９モルのテトラヒドロフラン溶液５
０ｍ１を還流下漬下し、さらに１時間還流した。(3) 5-((3S)-3-methylpentanoyl-2
-Preparation of (4-hebutylphenyl)pyridine 1-Bromo-(2
40 ml of a solution of 5.09 (0,033 mol) of S)-2-methylbutane in tetrahydrofuran was added dropwise at 25-30"C to prepare Grignille test straw II. To this solution, 5-
Cyano-2-(4-hebutylphenyl)pyridine 5.1
7(](00,019 mol of tetrahydrofuran solution 5
0 ml of the solution was soaked under reflux and further refluxed for 1 hour.
この反応溶液を冷却した塩酸水溶液に加え析出した結晶
を濾過後、エタノールから再結晶して５−（（３Ｓ）−
３−メチルペンタノイル−２−（４−へブチルフェニル
）ピリジン０．１２９を得た。 このものは液晶相を有
し、その相転移温度（” Ｃ）は次のとおりであった。This reaction solution was added to a cooled aqueous hydrochloric acid solution, and the precipitated crystals were filtered and then recrystallized from ethanol to give 5-((3S)-
0.129 of 3-methylpentanoyl-2-(4-hebutylphenyl)pyridine was obtained. This material had a liquid crystal phase, and its phase transition temperature ("C) was as follows.
Ｃｒ５Ｂ、５ （Ｓ、” ４９．２ＳＡ ５４．３）
ｌ莫施例２
本発明の化合物である実施例１の５−（（３Ｓ）−３−
メチルペンタノイル−２−（４−ヘプチルフェニル）ピ
リジン５重量％と
から成る混合物は、Ｓｃ’ Ｓａ ： ５４．０
・Ｃ，Ｓ、−一中ｌニア４．５ °Ｃの相転移温度を
示した。Cr5B,5 (S,” 49.2SA 54.3)
Example 2 5-((3S)-3- of Example 1, a compound of the present invention)
A mixture consisting of 5% by weight of methylpentanoyl-2-(4-heptylphenyl)pyridine has a Sc'Sa of 54.0.
・C, S, - showed a phase transition temperature of 4.5 °C.
（発明の効果）
本発明により新規な光学活性化合物が提供され、該化合
物を、Ｓｃ相を示す液晶材料と併せて用いることにより
、新規な強誘電性液晶組成物が提供される。(Effects of the Invention) The present invention provides a novel optically active compound, and by using this compound in combination with a liquid crystal material exhibiting an Sc phase, a novel ferroelectric liquid crystal composition is provided.
Claims (2)
くはアルコキシ基を表し、Ｒ＾＊は光学活性基、Ｘ＾１
、Ｘ＾２はそれぞれ独立に水素原子、ハロゲン原子又は
シアノ基、ｎは１又は２を表す。〕で表される光学活性
化合物。(1) The following general formula (I) ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) [In the formula (I), R represents an alkyl group or alkoxy group having 1 to 10 carbon atoms, and R^* is an optical Active group, X^1
, X^2 each independently represent a hydrogen atom, a halogen atom or a cyano group, and n represents 1 or 2. ] An optically active compound represented by
徴とする液晶組成物(2) A liquid crystal composition containing the optically active compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31644890A JPH04187676A (en) | 1990-11-21 | 1990-11-21 | Optically active compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31644890A JPH04187676A (en) | 1990-11-21 | 1990-11-21 | Optically active compound and liquid crystal composition containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04187676A true JPH04187676A (en) | 1992-07-06 |
Family
ID=18077204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31644890A Pending JPH04187676A (en) | 1990-11-21 | 1990-11-21 | Optically active compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04187676A (en) |
-
1990
- 1990-11-21 JP JP31644890A patent/JPH04187676A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS62223172A (en) | 2-(4'-alkoxyphenyl)-5-alkylpyridine | |
| JP2545251B2 (en) | Condensates of optically active 4- (1-hydroxyethyl) biphenyl and optically active organic acids | |
| JPH03193774A (en) | Optically active liquid crystal compound, liquid crystal composition containing same and liquid crystal element using this composition | |
| JPH04187676A (en) | Optically active compound and liquid crystal composition containing the same | |
| JPH0430954B2 (en) | ||
| JPS635084A (en) | 2-phenylpyrimidine derivative | |
| JPH02209873A (en) | Optically active 2,5-disubstituted pyrimidine derivative | |
| JPH01106870A (en) | 2, 5-diphenylpyrimidine compound, liquid crystal composition and electro-optical element | |
| JP2534079B2 (en) | Optically active compound, liquid crystal composition and electro-optical element | |
| JP2948862B2 (en) | Alkylphenylalkylpyrimidine compounds and compositions | |
| JPH058707B2 (en) | ||
| JPH04159264A (en) | Pyrimidine compound and liquid crystal composition containing the same | |
| JPH04217665A (en) | Branched phenylpyridine compound and liquid crystal composition containing the same | |
| JP2558476B2 (en) | Liquid crystalline compound | |
| JPH04211680A (en) | Pyridylpyrimidine compound and liquid crystal composition containing the same | |
| JP2583039B2 (en) | Citronellyloxyphenylpyrimidine derivative liquid crystal material | |
| JPH04193844A (en) | Optically active compound and liquid crystal composition containing the same | |
| JPH01128958A (en) | Alpha-aryloxypropionic acid esters | |
| JPH04288058A (en) | Phenylpyridine compound and liquid crystal composition containing the same | |
| JP2698459B2 (en) | Novel ether compound and liquid crystal composition containing the same | |
| JPH03287582A (en) | Liquid crystal | |
| JPH04159265A (en) | Branched phenylpyrimidine compound and liquid crystal composition containing the same | |
| JPH04178370A (en) | Phenylpyrimidine compound and liquid crystal composition containing the same compound | |
| JP2812398B2 (en) | Novel ether compound and liquid crystal composition containing the same | |
| JPH0236176A (en) | Pyridazine compound and liquid crystal composition |