(4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-isopropyloxazole | 169171-35-1

• 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-(2',4'-dihydroxyphenyl)-4-isopropyloxazole
• CAS: 169171-35-1
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: MTEJUHCQXJMLLX-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-碘癸烷 、 (4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-4-isopropyloxazole 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 17.0h， 以41%的产率得到(4S)-4,5-dihydro-2-(4'-decyloxy-2'-hydroxyphenyl)-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：

  2,4-二羟基苯甲醛肟 在 氢氧化钾 、 乙酸酐 、 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 21.0h， 生成 (4S)-4,5-dihydro-2-(2',4'-dihydroxyphenyl)-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