JPS63166850A - Novel liquid crystal compound - Google Patents
Novel liquid crystal compoundInfo
- Publication number
- JPS63166850A JPS63166850A JP61315705A JP31570586A JPS63166850A JP S63166850 A JPS63166850 A JP S63166850A JP 61315705 A JP61315705 A JP 61315705A JP 31570586 A JP31570586 A JP 31570586A JP S63166850 A JPS63166850 A JP S63166850A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- optically active
- carboxylic 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.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 abstract description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 4
- IWWNTISKHOYKAN-UHFFFAOYSA-N 4-(4-hexoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 IWWNTISKHOYKAN-UHFFFAOYSA-N 0.000 abstract description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000003205 fragrance Substances 0.000 description 10
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 3
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940007550 benzyl acetate Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229930007744 linalool Natural products 0.000 description 3
- 229940067107 phenylethyl alcohol Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- -1 2-substituted propionic acid Chemical class 0.000 description 2
- JTGCXYYDAVPSFD-UHFFFAOYSA-N 4-(4-hydroxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(O)C=C1 JTGCXYYDAVPSFD-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N 1-Phenylethyl acetate Chemical compound CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 1
- VKCNNDPZFOVURD-UHFFFAOYSA-N 2-naphthalen-1-ylpropanoic acid Chemical compound C1=CC=C2C(C(C(O)=O)C)=CC=CC2=C1 VKCNNDPZFOVURD-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- 102100024829 DNA polymerase delta catalytic subunit Human genes 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 101000868333 Homo sapiens Cyclin-dependent kinase 1 Proteins 0.000 description 1
- 101000909198 Homo sapiens DNA polymerase delta catalytic subunit Proteins 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940067137 musk ketone Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】 本発明は、新規な液晶性化合物に関する。[Detailed description of the invention] The present invention relates to a novel liquid crystal compound.
さらに詳しくは９本発明は一般式〔■〕〔式中 Ｈｌ、
Ｒ１はそれぞれ独立してＣ２ないしＣ１０の直鎖アル
キル基を、示す。〕で表される光学活性化合物またはそ
のラセミ体、および該化合物を含有する液晶組成物に関
する。More specifically, 9 the present invention has the general formula [■] [wherein Hl,
R1 each independently represents a C2 to C10 straight chain alkyl group. The present invention relates to an optically active compound represented by the following formula or its racemate, and a liquid crystal composition containing the compound.
従来、液晶化合物は１種々の電子光学的表示装置に液晶
材料として用いられている。最適な液晶物質の性質はそ
れぞれの表示方式により異なるが。Conventionally, liquid crystal compounds have been used as liquid crystal materials in a variety of electro-optical display devices. The optimal properties of liquid crystal materials differ depending on each display method.
水分、熱、空気、光、電場等に対して、物理的。Physically related to moisture, heat, air, light, electric fields, etc.
化学的かつ電気的に安定であることが要求される。It is required to be chemically and electrically stable.
加えて、液晶の温度範囲が広いこと、駆動電圧の低いこ
と、応答速度の速いこと１時分割特性の良好なこと、視
野角の広いことなども要求される。In addition, the liquid crystal is required to have a wide temperature range, a low driving voltage, a fast response speed, good one-time division characteristics, and a wide viewing angle.
しかし、単一化合物でこれらの諸条件を満足するものは
今のところ得られておらず、実用的には個々に優れた性
質をもつ数種類の液晶化合物又は非液晶化合物を混合し
て液晶組成物としである程度の使用に耐え得る材料を得
ているのが現状である。However, a single compound that satisfies these conditions has not yet been obtained, and in practice, liquid crystal compositions are prepared by mixing several types of liquid crystal compounds or non-liquid crystal compounds that each have excellent properties. At present, we have obtained materials that can withstand a certain level of use.
本発明の目的は、実用的性能に優れた液晶組成物の素材
として有利な化合物を提供することにある。本発明者ら
はこの目的で化合物中に２−置換プロピオン酸エステル
骨格を有するものを多数合成し１本発明化合物を見出す
に到った。An object of the present invention is to provide a compound that is advantageous as a material for a liquid crystal composition with excellent practical performance. For this purpose, the present inventors synthesized many compounds having a 2-substituted propionic acid ester skeleton and found one compound of the present invention.
本発明の化合物は、純粋な状態では無色ないし淡黄色で
あり、化学的に安定であって、広い液晶温度範囲を存す
る。さらに他の液晶物質１例えば。The compound of the present invention is colorless to pale yellow in its pure state, is chemically stable, and has a wide liquid crystal temperature range. Furthermore, other liquid crystal substances 1, for example.
既存のビフェニル系、フェニルシクロヘキサン系。Existing biphenyl type and phenylcyclohexane type.
安息香酸フェニルエステル系、シクロヘキサンカルボン
酸フェニルエステル系、シッフ塩基系、アゾキシ系、フ
ェニルピリミジン系、フェニルメタジオキサン系等との
相溶性に優れており、これらの液晶物質との混合によっ
て液晶温度範囲を広く。It has excellent compatibility with benzoic acid phenyl esters, cyclohexanecarboxylic acid phenyl esters, Schiff bases, azoxy systems, phenylpyrimidine systems, phenylmethadioxane systems, etc., and by mixing with these liquid crystal substances, the liquid crystal temperature range can be changed. Wide.
応答特性の優れた液晶組成物を構成する有用な成分であ
ることを見出した。It has been found that it is a useful component constituting a liquid crystal composition with excellent response characteristics.
本発明の化合物は種々の方法で製造できるが。The compounds of the invention can be prepared in a variety of ways.
例えば以下の方法によって製造される。For example, it is manufactured by the following method.
（１）４’−ｎ−アルキルオキシビフェニル−４−カル
ボン酸の酸クロリドと、２−（６−ヒドロキシ−２−ナ
フチル）プロピオン酸ｎ−アルキルの反応によるエステ
ル化。(1) Esterification by reaction of acid chloride of 4'-n-alkyloxybiphenyl-4-carboxylic acid and n-alkyl 2-(6-hydroxy-2-naphthyl)propionate.
（２）４’−ヒドロキシビフェニル−４−カルボン酸［
６’（１−（ｎ−アルキルオキシカルボニル）エチル〕
）−２°〜ナフチルの無水溶媒中、塩基存在下でのハロ
ゲン化ｎ−アルキルとの反応によるアルキル化
（３１２−（６−（４’−ｎ−アルキルオキシビフェニ
ル−４−カルボニルオキシ）−２−ナフチル〕プロピオ
ン酸の酸クロリドとｎ−アルキルアルコールの反応によ
るエステル化。(2) 4'-hydroxybiphenyl-4-carboxylic acid [
6'(1-(n-alkyloxycarbonyl)ethyl)
)-2° ~ Alkylation of naphthyl by reaction with n-alkyl halide in anhydrous solvent in the presence of a base (312-(6-(4'-n-alkyloxybiphenyl-4-carbonyloxy)-2 - Esterification of naphthyl propionic acid by reaction of acid chloride and n-alkyl alcohol.
などが挙げられる。Examples include.
以下、実施例を挙げてさらに詳細に説明するが。Hereinafter, the present invention will be explained in more detail with reference to examples.
本発明はこれらによって限定されるものではない。The present invention is not limited to these.
〔実施例１〕
光学活性な４′−ｎ−ヘキシルオキシビフェニル−４−
カルボン酸−６’−（ｎ−オクチルオキシカルボニル）
エチルオキシ）−２１−ナフチルの製造。[Example 1] Optically active 4'-n-hexyloxybiphenyl-4-
Carboxylic acid-6'-(n-octyloxycarbonyl)
Production of (ethyloxy)-21-naphthyl.
４′−ヒドロキシビフェニル−４−カルボン酸１゜３４
ｇの結晶０．４２８ｇに水酸化カリウム０．４５ｇ、エ
タノール６０ｍ１．水８１および臭化ヘキシル０．３９
６ｇを加え、１２時間加熱還流した。反応液２モル塩酸
４．５ｍｌを加え、晶析濾過後、粗結晶を再結晶にて精
製し４゛−ｎ−へキシルオキシビフェニル−４−カルボ
ン酸０．２９０ｇを得た。4'-Hydroxybiphenyl-4-carboxylic acid 1°34
g of crystals, 0.45 g of potassium hydroxide, and 60 ml of ethanol. 81 water and 0.39 hexyl bromide
6 g was added and heated under reflux for 12 hours. 4.5 ml of 2M hydrochloric acid was added to the reaction solution, and after crystallization and filtration, the crude crystals were purified by recrystallization to obtain 0.290 g of 4'-n-hexyloxybiphenyl-4-carboxylic acid.
次に、この結晶０．５９７ｇを塩化チオニル４ｍｌ中１
時間加熱還流させて酸クロリドとした。過剰の塩化チオ
ニルを微圧下留去した後、クロロホルム１０ｍ１． ピ
リジン２ＩＩｌｌおよび光学活性な２−（６−ヒドロキ
シ−２−ナフチル）プロピオン酸−ｎ−オクチル０．７
０ｇ
（（αｏｏ ＋２８．６’ （ｃ＝０．５３．クロ
ロホルム）
を加え、２時間加熱還流した。反応液を１モル塩酸８ｍ
ｌで中和し、セライト濾過後、濾液をクロロホルムで抽
出し、クロロホルムを留去した。得られた粗精物を精製
し、光学活性な４′−ｎ−ヘキシルオキシビフェニル−
４−カルボン酸６’−（ｌ−ｎ−オクチルオキシカルボ
ニル）エチルオキシ）−２１ナフチル０．４６ｇを得た
。Next, 0.597 g of this crystal was added to 1 ml of thionyl chloride.
The mixture was heated under reflux for a period of time to form an acid chloride. After distilling off excess thionyl chloride under slight pressure, 10 ml of chloroform was added. Pyridine 2IIIll and optically active n-octyl 2-(6-hydroxy-2-naphthyl)propionate 0.7
0 g ((αoo +28.6' (c=0.53.chloroform)) was added and heated under reflux for 2 hours.
After filtering through Celite, the filtrate was extracted with chloroform, and the chloroform was distilled off. The obtained crude product was purified to obtain optically active 4'-n-hexyloxybiphenyl-
0.46 g of naphthyl 4-carboxylic acid 6'-(l-n-octyloxycarbonyl)ethyloxy)-21 was obtained.
〔α〕。 ＋１２．９’ （ｃ＝０．８３．クロロホ
ルム）
Ｉ Ｒ（）［Ｂｒ） ： ２９０帆１７３０．１６００
，１１７０．１１４０．１０７０゜７６０ｃｍ ”’
Ｎ Ｍ Ｒ（ＣＤＣ１３）
δ０．７〜１．９ （ｍ、６Ｈ）、 １．５６（ｄ、Ｊ
＝７！Ｉｚ、３Ｈ）３．８〜４．３（ｍ、５）１）、６
．８〜８．３（ｍ、１４１（）Ｍ Ｓ （ｍ／ｅ）
： ６０８（Ｍ” 、？）、２８１（１００）、２５３
（２２）２時間攪拌した。反応終了後、反応液を冷却し
たのち、１ｔの水中に注ぎ、イノプロピルエーテル３０
０１Ｌｌで抽出する。有機層を１０ ’ｌｋ ＮａＯＨ
液１００ｄで２回、飽和食塩水１０（１／で２回洗浄し
たのチ、ロータリーエバポレーターでイノプロピルエー
テルを蒸発除去した。得られた残留物を精密蒸留し、沸
点９０〜９５℃／１．５■Ｈｇの留分１８０ｇを得た。[α]. +12.9' (c=0.83.Chloroform) I R() [Br): 290 sails 1730.1600
,1170.1140.1070゜760cm ''' NMR (CDC13) δ0.7~1.9 (m, 6H), 1.56 (d, J
=7! Iz, 3H) 3.8-4.3 (m, 5) 1), 6
．． 8-8.3 (m, 141 () M S (m/e)
: 608 (M", ?), 281 (100), 253
(22) Stirred for 2 hours. After the reaction was completed, the reaction solution was cooled, poured into 1 t of water, and inopropyl ether 30
Extract with 01Ll. The organic layer was diluted with 10'lk NaOH.
The inopropyl ether was washed twice with 100 d of liquid and twice with 10 d of saturated saline solution, and the inopropyl ether was removed by evaporation using a rotary evaporator.The resulting residue was precision distilled to a boiling point of 90-95°C/1. 180 g of a fraction of 5■Hg was obtained.
このオイルの分析結果を次に示す。The analysis results of this oil are shown below.
ＣＩ−ＭＳ （Ｍ＋計算値 １７３）
’Ｈ−ＮＭＲ（δ、 ＴＭＳ基準、 ＣＤＣ２，溶液）
１．２４ 、１．３３ （３Ｈ＠ａａｈ ｊｂｏｔｈ
ｄ 、 Ｊ＝７．７Ｈｚ）１．５０〜２．２０（２Ｈ，
ｍ）
２．５２，２．９２（ＩＨｅａｃｈ、ｂｏｔｈｔｑ、
Ｊ＝７．７，７．７Ｈｚ）７．１０〜７．４９（５Ｈ，
ｍ）
上記の分析結果より、このオイルが２−シアノ−４−７
エニルペンタンであることを確認した。CI-MS (M+calculated value 173) 'H-NMR (δ, TMS standard, CDC2, solution)
1.24 , 1.33 (3H@aah jboth
d, J=7.7Hz) 1.50-2.20 (2H,
m) 2.52, 2.92 (IHeach, bothtq,
J=7.7, 7.7Hz) 7.10-7.49 (5H,
m) From the above analysis results, this oil is 2-cyano-4-7
It was confirmed that it was enylpentane.
実施例２
２−シアノ−４−７エニルペンタンの５１ｉ１１部を次
の処方によシ得られたムｌ’ −（Ｍｕｇｕ＠ｔ ）調
の香気を持つ香料成分の９５重量部に配合した。Example 2 11 parts of 51i of 2-cyano-4-7enylpentane were blended with 95 parts by weight of a fragrance ingredient having a mul'-(Mugu@t) aroma obtained by the following formulation.
重量部
ヒドロキシシトロネラール ２０フエニルエチル
アルコール １．５酢酸リナリル
１０
テルピネオール ５酢酸ベンジル
５ｒラニオール
５リナロール １゜シト
ロネロール ８ヘキシルシンナミツ
クアルデヒド ３イランイラン油
２ゼラニウム油 ２
α−ヨノン ３
ジャスミン・アブソリュート ２ヘリオト
ロピン ２ムスクケトン
３
このようにして得られた香気組成物は上記の２−シアノ
−４−フェニルインタンを含まない香料組成物に比較し
て深みのあるムグー調の香気を有していた。なお、２−
シアノ−４−フェニルインタンは他の香料素材竜よく調
和した。Parts by weight Hydroxycitronellal 20 Phenylethyl alcohol 1.5 Linalyl acetate
10 Terpineol 5 Benzyl acetate
5r Raniol
5 Linalool 1゜Citronellol 8 Hexylcinnamic aldehyde 3 Ylang-ylang oil
2 geranium oil 2
α-ionone 3 Jasmine absolute 2 Heliotropin 2 Musk ketone
3 The fragrance composition thus obtained had a deeper mughu-like fragrance compared to the above-mentioned fragrance composition not containing 2-cyano-4-phenylintane. In addition, 2-
Cyano-4-phenylintane blended well with other fragrance materials.
実施例３
２−シアノ−４−７エニル４ンタンの８重量部を次の処
方によシ得られたガーデニア（Ｃａｒｄｅｎｌｍ）調の
香気を持つ香料成分の９２重量部に配合した。Example 3 8 parts by weight of 2-cyano-4-7enyl 4-ethane was blended with 92 parts by weight of a perfume ingredient having a gardenia-like aroma obtained according to the following formulation.
重量部
メチルフェニルカルビニルアセテート ５ジメ
チルベ／ジルカルビノール １０ヒドロキシシト
ロネラール １０ペルがモット
５ネ“−ル ５
酢酸ベンジル １０フエニルエチル
アルコール １０メチルヨノン
５リナロール １０
トルパルサム ３ヘリオトロピン
３ジヤスミン・アブソリュート
２０−ズ・アブソリュート ２
ガルパナム油 ３ベチバー油
３サンダルウツド油
２パ ニ リ ン
２ムスクケトン
２このようにして得られた香気組成物は上記の２−シ
アノ−４−フェニルインタンを含まない香料組成物に比
較して深みのあるガーデニア調の香気を有していた。な
お、２−シアノ−４−７エニルペンタンは他の香料素材
とよく調和した。Parts by weight Methylphenyl carbinyl acetate 5 Dimethyl be/zyl carbinol 10 Hydroxycitronellal 10 Pels
5 Nerule 5 Benzyl acetate 10 Phenylethyl alcohol 10 Methylionone
5 Linalool 10 Tolparsum 3 Heliotropin 3 Diasmine Absolute
20-'s Absolute 2
Galpanum oil 3 Vetiver oil
3 Sandalwood oil
2 pantyhose
2 musk ketones
2 The fragrance composition thus obtained had a deeper gardenia-like fragrance compared to the above-mentioned fragrance composition not containing 2-cyano-4-phenylintane. In addition, 2-cyano-4-7enylpentane harmonized well with other fragrance materials.
実施例４
２−−７７／−４−フェニルペンタンの５ ｉｔｉ部を
次の処方によシ得られたローズ（ＲｏＳ・）調の香気を
持つ香料組成物の９５重量部に配合し九。Example 4 5 parts of 2-77/-4-phenylpentane were blended into 95 parts by weight of a fragrance composition having a rose (RoS.) aroma obtained by the following formulation.
重量部
フェニルエチルアルコール ２０ｒラニオー
ル ２０
シトロネロール ８リナロール
５
酢酸ベンジル ５α−ヨノン
３Parts by weight Phenylethyl alcohol 20r Raniol 20 Citronellol 8 Linalool
5 Benzyl acetate 5α-ionone
3
Claims (2)
＿１＿６の直鎖アルキル基を示す。〕で表される光学活
性化合物またはそのラセミ体。(1) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R^1R^2 each independently represents C_2 or C
Indicates the straight chain alkyl group of _1_6. ] or its racemate.
しＣ＿１＿６の直鎖アルキル基を示す。〕で表される光
学活性化合物の１種または２種以上を含有することを特
徴とする液晶組成物。(2) General formula [I]: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R^1 and R^2 each independently represent a C_2 to C_1_6 linear alkyl group. A liquid crystal composition containing one or more optically active compounds represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61315705A JPH0737420B2 (en) | 1986-12-27 | 1986-12-27 | Novel liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61315705A JPH0737420B2 (en) | 1986-12-27 | 1986-12-27 | Novel liquid crystal compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63166850A true JPS63166850A (en) | 1988-07-11 |
| JPH0737420B2 JPH0737420B2 (en) | 1995-04-26 |
Family
ID=18068552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61315705A Expired - Lifetime JPH0737420B2 (en) | 1986-12-27 | 1986-12-27 | Novel liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0737420B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061399A (en) * | 1986-04-28 | 1991-10-29 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Optically active naphthalene compounds and liquid crystal materials and devices incorporating them |
| US5072021A (en) * | 1986-12-26 | 1991-12-10 | Mitsui Toatsu Chemicals, Inc. | Optically active naphthalene derivatives |
-
1986
- 1986-12-27 JP JP61315705A patent/JPH0737420B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5061399A (en) * | 1986-04-28 | 1991-10-29 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Optically active naphthalene compounds and liquid crystal materials and devices incorporating them |
| US5072021A (en) * | 1986-12-26 | 1991-12-10 | Mitsui Toatsu Chemicals, Inc. | Optically active naphthalene derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0737420B2 (en) | 1995-04-26 |
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