(4S)-4,5-dihydro-2-(4'-hydroxyphenyl)-4-isopropyloxyoxazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4S)-4,5-dihydro-2-(4'-hydroxyphenyl)-4-isopropyloxyoxazole
• 英文别名: (S)-4-isopropyl-2-(4-hydroxyphenyl)-1,3-oxazoline；4-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenol
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: OCOJMYVNHWWTOV-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-decyloxybenzoyl chloride 、 (4S)-4,5-dihydro-2-(4'-hydroxyphenyl)-4-isopropyloxyoxazole 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(4S)-4,5-dihydro-2-<4'-(4''-decyloxybenzoyloxy)phenyl>-4-isopropyloxazole
  参考文献：
  名称：

  Improving FLC Properties. Simplicity, Planarity, and Rigidity in New Chiral Oxazoline Derivatives

  摘要：

  In an attempt to develop new dopants for improved ferroelectric properties in liquid crystals, aryloxazolines have been chosen as chiral moieties. They were prepared in optically active form from (s)-beta-amino alcohols via a short stereospecific synthesis and incorporated into mesogenic systems. Mesogenic and ferroelectric properties of 11 compounds in five series of chiral oxazoline derivatives [I(OH), I(H), II(OH), II(H), and III(OH)] have been studied. In order to establish the relationship between the molecular structure and ferroelectric properties, an in-depth structural investigation of both H-bonded and non-H-bonded phenyloxazoline moieties was carried out (by means of semiempirical calculations-AM1-and spectroscopic studies-IR, UV and H-1 NMR). These studies have proved a planar structure for both types of structures, which should have a strong influence on ferroelectric properties. These properties have been evaluated in 10 mol % binary mixtures. The highest Ps values were measured for compounds of series I(OH) [P-s max(I(OH)a) = 16.7 nC/cm(2), P-s max(I(OH)b) = 13.2 nC/cm(2)] containing a hydrogen bond, which makes the chiral part of the molecule more rigid. Compound III(OH)a shows a wide SmC* phase range which supercools well below room temperature, and it has been studied as a ferroelectric liquid crystal in the pure state. The P-s max measured is appreciably high: 225 nC/cm(2). Its special thermal behavior (showing a glass transition at -28 degrees C) makes this compound very interesting from the point of view of practical applications and will be the target of further studies.

  DOI：

  10.1021/ja00137a003
• 作为产物：
  描述：

  L-缬氨醇 、 对羟基苯甲酸甲酯 在 Zn₄(OCOCF₃)6O 作用下， 以 氯苯 为溶剂， 反应 12.0h， 以58%的产率得到(4S)-4,5-dihydro-2-(4'-hydroxyphenyl)-4-isopropyloxyoxazole
  参考文献：
  名称：

  CONDENSATION REACTION BY METAL CATALYST

  摘要：

  公开号：

  EP1958940B1

文献信息

• Condensation reaction by metal catalyst
  申请人：Takasago International Corporation

  公开号：US07888513B2

  公开（公告）日：2011-02-15

  The invention relates to a method for producing an azoline compound represented by the general formula (3): wherein R1 represents an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; R3, R4, R5 and R6 may be the same or different and each represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; two arbitrary groups selected from R3, R4, R5 and R6 may bond to each other to form a ring; and Z1 represents an oxygen atom, a sulfur atom or a selenium atom; comprising reacting a carboxylic acid or a carboxylic acid derivative represented by the general formula (1): R1CO2R2  (1) wherein R1 is as defined above; R2 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group; and R1 and R2 may bond to each other to form a ring; with an aminochalcogenide represented by the general formula (2): wherein R3, R4, R5, R6 and Z1 are as defined above; in the presence of a compound containing a group 12 metal element in the periodic table.

  本发明涉及一种制备一种由通式（3）表示的氮杂环化合物的方法：其中R1表示可选取代的碳氢基团，可选取代的烷氧基团，可选取代的烷氧羰基团，卤素原子，取代的氨基团，取代的氨基甲酰基团或可选取代的杂环基团；R3、R4、R5和R6可以相同也可以不同，每个表示氢原子，可选取代的碳氢基团，可选取代的烷氧基团，可选取代的烷氧羰基团，卤素原子，取代的氨基团，取代的氨基甲酰基团或可选取代的杂环基团；从R3、R4、R5和R6中任选两个基团可以结合形成一个环；Z1表示氧原子，硫原子或硒原子；包括在周期表中含有12号族金属元素的化合物存在下，将通式（1）表示的羧酸或羧酸衍生物：R1CO2R2（1）其中R1如上所定义；R2表示氢原子，可选取代的烷基团或可选取代的芳基团；R1和R2可以结合形成一个环；与通式（2）表示的氨基硫族化合物反应：其中R3、R4、R5、R6和Z1如上所定义。
• Condensation Reaction by Metal Catalyst
  申请人：Mashima Kazushi

  公开号：US20090198070A1

  公开（公告）日：2009-08-06

  The invention relates to a method for producing an azoline compound represented by the general formula (3): wherein R 1 represents an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; R 3 , R 4 , R 5 and R 6 may be the same or different and each represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, a halogen atom, a substituted amino group, a substituted carbamoyl group or an optionally substituted heterocyclic group; two arbitrary groups selected from R 3 , R 4 , R 5 and R 6 may bond to each other to form a ring; and Z 1 represents an oxygen atom, a sulfur atom or a selenium atom; comprising reacting a carboxylic acid or a carboxylic acid derivative represented by the general formula (1): R 1 CO 2 R 2 (1) wherein R 1 is as defined above; R 2 represents a hydrogen atom, an optionally substituted alkyl group or an optionally substituted aryl group; and R 1 and R 2 may bond to each other to form a ring; with an aminochalcogenide represented by the general formula (2): wherein R 3 , R 4 , R 5 , R 6 and Z 1 are as defined above; in the presence of a compound containing a group 12 metal element in the periodic table.

  本发明涉及一种制备由通式（3）表示的氮杂环化合物的方法：其中R1表示可选取代的烃基、可选取代的烷氧基、可选取代的烷氧羰基、卤素原子、取代的氨基基团、取代的氨基甲酰基团或可选取代的杂环基团；R3、R4、R5和R6可以相同也可以不同，每个表示氢原子、可选取代的烃基、可选取代的烷氧基、可选取代的烷氧羰基、卤素原子、取代的氨基基团、取代的氨基甲酰基团或可选取代的杂环基团；从R3、R4、R5和R6中任选两个基团可以结合形成环；Z1表示氧原子、硫原子或硒原子；包括在周期表中含有12号族金属元素的化合物存在下，将由通式（1）表示的羧酸或羧酸衍生物与由通式（2）表示的氨基硫、氨基硒或氨基氧化合物反应。其中，R1、R2、R3、R4、R5、R6和Z1的含义如上所述。
• US7888513B2
  申请人：——

  公开号：US7888513B2

  公开（公告）日：2011-02-15
• CONDENSATION REACTION BY METAL CATALYST
  申请人：Takasago International Corporation

  公开号：EP1958940B1

  公开（公告）日：2013-06-26
• Improving FLC Properties. Simplicity, Planarity, and Rigidity in New Chiral Oxazoline Derivatives
  作者：Jose Luis Serrano、Teresa Sierra、Yolanda Gonzalez、Carsten Bolm、Konrad Weickhardt、Angelika Magnus、Guido Moll

  DOI：10.1021/ja00137a003

  日期：1995.8

  In an attempt to develop new dopants for improved ferroelectric properties in liquid crystals, aryloxazolines have been chosen as chiral moieties. They were prepared in optically active form from (s)-beta-amino alcohols via a short stereospecific synthesis and incorporated into mesogenic systems. Mesogenic and ferroelectric properties of 11 compounds in five series of chiral oxazoline derivatives [I(OH), I(H), II(OH), II(H), and III(OH)] have been studied. In order to establish the relationship between the molecular structure and ferroelectric properties, an in-depth structural investigation of both H-bonded and non-H-bonded phenyloxazoline moieties was carried out (by means of semiempirical calculations-AM1-and spectroscopic studies-IR, UV and H-1 NMR). These studies have proved a planar structure for both types of structures, which should have a strong influence on ferroelectric properties. These properties have been evaluated in 10 mol % binary mixtures. The highest Ps values were measured for compounds of series I(OH) [P-s max(I(OH)a) = 16.7 nC/cm(2), P-s max(I(OH)b) = 13.2 nC/cm(2)] containing a hydrogen bond, which makes the chiral part of the molecule more rigid. Compound III(OH)a shows a wide SmC* phase range which supercools well below room temperature, and it has been studied as a ferroelectric liquid crystal in the pure state. The P-s max measured is appreciably high: 225 nC/cm(2). Its special thermal behavior (showing a glass transition at -28 degrees C) makes this compound very interesting from the point of view of practical applications and will be the target of further studies.