Systematization of optical resolution and development of new chiral materials

光学拆分的系统化和新型手性材料的开发

• 批准号: 08455411
• 负责人: NOHIRA Hiroyuki
• 金额: $ 3.39万
• 依托单位: Saitama University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 1996
• 资助国家: 日本
• 起止时间: 1996 至 1997
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-08455411/
• 关键词: optical resolution; chiral compound; resolving agent; crystallization method; resolving efficiency; medicine; perfume; liquid crystal; キラル; X線構造解析; キラルスルホン酸; キラルホスホン酸; 反強誘電性液晶

We have mainly studied on optical resolutions with crystallization method. Sclareolide was resolved by erythro-2-amino-1,2-diphenylethanol, and a natural type of Ambrox was synthesized from the optically active Sclareolide. gamma-Nonyllactone which was a chief ingredient of coconut flavor was resolved by 1-naphtylethylamine. 3-Hydroxy-4-butanolide which was useful for synthesis of medicinal compounds was resolved, and some optically active compounds having a five-membered ring structure were derived from it.New chiral amines and aminoalchols having a condensed-ring structure, namely 1-aminoindane and 1-amino-2-hydroxy-1,2,3,4-tetrahydronaphtalene were synthesized and resolved. Many kind of carboxylic acids were resolved by the optically active amines and aminoalchols, and a relationship between molecular structure of resolving agents and their resolving ability was discussed.Using optically active cyanohydrins resolved by trans-2-benzamidocyclohexane carboxylic acid, some ferroelectric liquid crystals were synthesized, and their ferroelectricities were evaluated.Optically active chroman-2-carboxylic acid derivatives were synthesized, and their absolute configurations were determined by the circular dichromism. Some chiral nematic materials were synthesized using chroman-2-carboxylic acid, and their helical twisting powers were evaluated.

我们主要研究了结晶法的光学分辨率。用赤基-2-氨基-1，2-二苯乙醇拆分Sclareolide，并由光学活性Sclareolide合成了一种天然类型的Ambrox。以1-萘乙胺为拆分试剂，对椰子香精的主要成分--γ-壬基内酯进行了拆分。拆分了用于合成药物的3-羟基-4-丁内酯，并由此衍生出一些具有五元环结构的光学活性化合物；合成并拆分了具有稠环结构的手性胺和氨基醇，即1-氨基吲哚和1-amino-2-hydroxy-1，2，3，4-tetrahydronaphtalene。用旋光性的胺和氨基醇拆分了多种羧酸，讨论了拆分剂的分子结构与拆分能力的关系；利用反式-2-苯甲酰胺环己烷羧酸拆分的光学活性氰醇合成了一些铁电液晶，并对其铁电性进行了评价；合成了光学活性的2-色氨酸衍生物，并用圆二色谱确定了它们的绝对构型。以2-铬甲酸为原料合成了一些手性向列相材料，并对它们的螺旋扭转力进行了评价。

项目成果

H. Liu: "SYNTHESIS OF SHMI‐PERFLUORINATED FLCs AND THE EFFECT OF FLUORINATION EXTENT ON MESOMORPHIC PROPERTIES" Molecular Crystals and Liquid Crystals. 302. 247-252 (1997)

H. Liu：“SHMI-全氟化 FLC 的合成以及氟化程度对介晶性质的影响”《分子晶体和液晶》302. 247-252 (1997)

Aoki Y.: "Novel antiferroelectric liquid crystals with a trifluoromethyl group at the chiral center" Ferroelectrics. 178. 213-220 (1996)

Aoki Y.：“手性中心具有三氟甲基的新型反铁电液晶”铁电体。

H.Liu: "SYNTHESIS OF SEMI-PERFLUORINATED FLCs AND THE EFFECT OF FLUORINATION EXTENT ON MESOMORPHIC PROPERTIES" Molecular Crystals and Liquid Crystals. 302. 247-252 (1997)

H.Liu：“半全氟FLC的合成以及氟化程度对介晶性质的影响”分子晶体和液晶。

Y.Aoki: "A novel ferroelectric liquid crystal having a trifluoromethyl group at the chiral center" Liquid Crystals. 23. 87-92 (1997)

Y.Aoki：“一种在手性中心具有三氟甲基的新型铁电液晶”液晶。

H.Liu: "SYNTHESIS OF SEMI-PERFLUORINATED FLSs AND THE EFFECT OF FLUORINATION EXTENT ON MESOMORPHIC PROPERTIES" Molecular Crystals and Liquid Crystals. 302. 247-252 (1997)

H.Liu：“半全氟FLS的合成以及氟化程度对介晶性质的影响”分子晶体和液晶。