4-chlorobenzyl 3-(4-hydroxyphenyl)acrylate | 117417-59-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-chlorobenzyl 3-(4-hydroxyphenyl)acrylate
• 英文别名: 4-hydroxy-4'-chlorobenzyl cinnamate；(4-chlorophenyl)methyl 3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 117417-59-1
• 化学式: C₁₆H₁₃ClO₃
• 分子量: 288.73
• InChiKey: MUYHIIGDDRGLIS-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C
• 沸点：
  442.2±30.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-chlorobenzyl 3-(4-hydroxyphenyl)acrylate 、 4-已氧基苯甲酰氯 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Mesomorphism dependence on molecular rigidity with reference to ‒CH˭CH‒ unit of central bridge

  摘要：

  A novel ester homologous series of rich mesomorphism and low temperatures with unexpected phase behaviors of eleven homologues was synthesized and studied with a view to understanding and establishing the relation between mesomorphic behaviour and the molecular structure of a series 4-(4 '-n-alkoxybenzoyloxy)-4 ''-chlorobenzyl cinnamates. All the members of the novel series are enantiotropically smectogenic and the octyloxy (C-8) to hexadecyloxy (C-16) homologues are enantiotropically nematogenic, in addition to smectogenic. Odd-even effect is observed for Sm-I/Sm-N transition curve but it is absent for N-I transition curve. Textures of nematic phase are threaded or Schlieren and that of the smectic phase are fan shaped or batonates of smectic-A type phase or Smectic-C type for C-16 homologues as judged directly from a heating stage of an optical polarizing microscopy. Analytical and spectral data confirmed the molecular structures of novel homologues. Mesomorphic properties of present series are compared with the structurally similar other known series. The average smectic and nematic thermal stabilities are 92.78 degrees C and 100.8 degrees C, respectively. Mesophase length minimum to maximum for smectic and nematic are 21.0 degrees C to 31.1 degrees C and 8.4 degrees C to 42.6 degrees C respectively. Thus, the present novel series is partly nematogenic and fully smectogenic with considerable degree of mesomorphism and low melting type.

  DOI：

  10.1080/15421406.2015.1069004
• 作为产物：
  描述：

  对羟基肉桂酸 、 4-氯苄溴 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到4-chlorobenzyl 3-(4-hydroxyphenyl)acrylate
  参考文献：
  名称：

  Mesomorphism dependence on molecular rigidity with reference to ‒CH˭CH‒ unit of central bridge

  摘要：

  A novel ester homologous series of rich mesomorphism and low temperatures with unexpected phase behaviors of eleven homologues was synthesized and studied with a view to understanding and establishing the relation between mesomorphic behaviour and the molecular structure of a series 4-(4 '-n-alkoxybenzoyloxy)-4 ''-chlorobenzyl cinnamates. All the members of the novel series are enantiotropically smectogenic and the octyloxy (C-8) to hexadecyloxy (C-16) homologues are enantiotropically nematogenic, in addition to smectogenic. Odd-even effect is observed for Sm-I/Sm-N transition curve but it is absent for N-I transition curve. Textures of nematic phase are threaded or Schlieren and that of the smectic phase are fan shaped or batonates of smectic-A type phase or Smectic-C type for C-16 homologues as judged directly from a heating stage of an optical polarizing microscopy. Analytical and spectral data confirmed the molecular structures of novel homologues. Mesomorphic properties of present series are compared with the structurally similar other known series. The average smectic and nematic thermal stabilities are 92.78 degrees C and 100.8 degrees C, respectively. Mesophase length minimum to maximum for smectic and nematic are 21.0 degrees C to 31.1 degrees C and 8.4 degrees C to 42.6 degrees C respectively. Thus, the present novel series is partly nematogenic and fully smectogenic with considerable degree of mesomorphism and low melting type.

  DOI：

  10.1080/15421406.2015.1069004

文献信息

• Melanogenesis Inhibition by Mono-hydroxycinnamic Ester Derivatives in B16 Melanoma Cells
  作者：Kyung-Dong Kim、Min-Ho Song、Eul-Kgun Yum、Ok-Seon Jeon、Young-Woon Ju、Moon-Sik Chang

  DOI：10.5012/bkcs.2010.31.01.181

  日期：2010.1.20