2,3-dimethoxy-1-methylphenanthrene-9-carboxaldehyde | 144412-72-6

• 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-dimethoxy-1-methylphenanthrene-9-carboxaldehyde
• 英文别名: 2,3-Dimethoxy-1-methylphenanthrene-9-carbaldehyde
• CAS: 144412-72-6
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: TYKQSIMQZABSPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-1-methylphenanthrene-9-carboxaldehyde 在 potassium tert-butylate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (8E,17E,26E)-6,7,15,16,24,25-hexamethoxytriphenanthro<8,9,10-abc:8,9,10-ghi:8,9,10-mno>cyclooctadecene
  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：

  1,1-二氯甲醚 、 2,3-dimethoxy-1-methylphenanthrene 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到2,3-dimethoxy-1-methylphenanthrene-9-carboxaldehyde
  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.