2,3-bis(hexyloxy)-1-methylphenanthrene | 144412-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,3-bis(hexyloxy)-1-methylphenanthrene
• 英文别名: 2,3-Dihexoxy-1-methylphenanthrene
• CAS: 144412-71-5
• 化学式: C₂₇H₃₆O₂
• 分子量: 392.582
• InChiKey: ZHEXAYXTGMKTMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(hexyloxy)-1-methylphenanthrene 在 四氯化锡 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (E)-N-phenyl-2,3-dimethoxy-1-methylphenanthren-9-imine
  参考文献：
  名称：

  [abc]-Annelated [18]annulenes

  摘要：

  A 3-fold stereoselective cyclocondensation of the azomethines 3 and 11 yields the [18]annulenes 4 and 12, respectively. The [abc]-annelation of naphthalene or phenanthrene systems realized here for the first time, leads to nonplanar molecules consisting of 'aromatic islands", which are connected by (E)-configured olefinic bridges. The absence of a diamagnetic ring current rules out a macrocyclic aromaticity. The NMR investigation, based on selective deuterations, is sustained by force field calculations (MMX). The disc-like compounds represent discotic mesogens of an enormous diameter. The formation of thermotropic liquid crystals can be achieved by the introduction of long flexible alkoxy chains.

  DOI：

  10.1021/jo00051a033
• 作为产物：
  描述：

  (E,Z)-1-(3,4-bis(hexyloxy)-2-methylphenyl)-2-phenylethene 在 碘 作用下， 以 环己烷 为溶剂， 反应 42.0h， 以75%的产率得到2,3-bis(hexyloxy)-1-methylphenanthrene
  参考文献：
  名称：

  [abc]-Annelated [18]annulenes

  摘要：

  A 3-fold stereoselective cyclocondensation of the azomethines 3 and 11 yields the [18]annulenes 4 and 12, respectively. The [abc]-annelation of naphthalene or phenanthrene systems realized here for the first time, leads to nonplanar molecules consisting of 'aromatic islands", which are connected by (E)-configured olefinic bridges. The absence of a diamagnetic ring current rules out a macrocyclic aromaticity. The NMR investigation, based on selective deuterations, is sustained by force field calculations (MMX). The disc-like compounds represent discotic mesogens of an enormous diameter. The formation of thermotropic liquid crystals can be achieved by the introduction of long flexible alkoxy chains.

  DOI：

  10.1021/jo00051a033

文献信息

• [abc]-Annelated [18]annulenes
  作者：Herbert Meier、Holger Kretzschmann、Heinz Kolshorn

  DOI：10.1021/jo00051a033

  日期：1992.12

  A 3-fold stereoselective cyclocondensation of the azomethines 3 and 11 yields the [18]annulenes 4 and 12, respectively. The [abc]-annelation of naphthalene or phenanthrene systems realized here for the first time, leads to nonplanar molecules consisting of 'aromatic islands", which are connected by (E)-configured olefinic bridges. The absence of a diamagnetic ring current rules out a macrocyclic aromaticity. The NMR investigation, based on selective deuterations, is sustained by force field calculations (MMX). The disc-like compounds represent discotic mesogens of an enormous diameter. The formation of thermotropic liquid crystals can be achieved by the introduction of long flexible alkoxy chains.