tert-butyl (+/-)-3-(2-naphthalenylmethylene)cyclobutanecarboxylate | 145549-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl (+/-)-3-(2-naphthalenylmethylene)cyclobutanecarboxylate
• CAS: 145549-80-0
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: CWQSZDFKFOWPPX-GDNBJRDFSA-N

物化性质

• 沸点：
  426.3±14.0 °C(predicted)
• 密度：
  1.132±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (+/-)-3-(2-naphthalenylmethylene)cyclobutanecarboxylate 在 氢溴酸 、 十六烷基三甲基溴化铵 作用下， 反应 1.5h， 以82%的产率得到(+/-)-3-(2-naphthalenylmethylene)cyclobutanecarboxylic acid
  参考文献：
  名称：

  Photochemistry of axially chiral (arylmethylene)cycloalkanes: a search for suitable photoswitchable liquid crystalline materials

  摘要：

  A series of chiral (arylmethylene)cycloalkanes was synthesized in racemic and optically active form to examine their suitability for incorporation in a liquid crystal-based optical switch. Irradiation of these compounds with UV light leads to their rapid photoracemization and, in some cases, their simultaneous destruction. The absorption spectra and circular dichroism spectra of these optically active compounds were determined. Chiral exciton coupling theory proves to be a good guide for predicting the magnitude of DELTAepsilon and glambda, (the Kuhn anisotropy factor). Addition of the optically active (arylmethylene)cycloalkanes to nematic liquid crystal materials induces cholesteric behavior. The helical twisting power (beta(M)) was determined for each compound, and a limit of 90 mum was established for the detection of a long-pitch cholesteric liquid crystal. Irradiation of the cholesteric liquid crystals formed by addition of the optically active (arylmethylene)cycloalkanes induces the transition to a compensated nematic phase that is readily sensed by optical microscopy.

  DOI：

  10.1021/jo00053a021
• 作为产物：
  描述：

  3-氧代环丁烷基羧酸 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 生成 tert-butyl (+/-)-3-(2-naphthalenylmethylene)cyclobutanecarboxylate
  参考文献：
  名称：

  Photochemistry of axially chiral (arylmethylene)cycloalkanes: a search for suitable photoswitchable liquid crystalline materials

  摘要：

  A series of chiral (arylmethylene)cycloalkanes was synthesized in racemic and optically active form to examine their suitability for incorporation in a liquid crystal-based optical switch. Irradiation of these compounds with UV light leads to their rapid photoracemization and, in some cases, their simultaneous destruction. The absorption spectra and circular dichroism spectra of these optically active compounds were determined. Chiral exciton coupling theory proves to be a good guide for predicting the magnitude of DELTAepsilon and glambda, (the Kuhn anisotropy factor). Addition of the optically active (arylmethylene)cycloalkanes to nematic liquid crystal materials induces cholesteric behavior. The helical twisting power (beta(M)) was determined for each compound, and a limit of 90 mum was established for the detection of a long-pitch cholesteric liquid crystal. Irradiation of the cholesteric liquid crystals formed by addition of the optically active (arylmethylene)cycloalkanes induces the transition to a compensated nematic phase that is readily sensed by optical microscopy.

  DOI：

  10.1021/jo00053a021