[2.2]paracyclophane-4,7-dicarboxylic acid | 478494-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2.2]paracyclophane-4,7-dicarboxylic acid
• 英文别名: tricyclo[8.2.2.2^4,7]hexadeca-4,6,10,12,13,15-hexaene-5,15-dicarboxylic acid；Tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaene-5,15-dicarboxylic acid；tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaene-5,15-dicarboxylic acid
• CAS: 478494-90-5
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: ZLQDLBGLTAAQIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2.2]paracyclophane-4,7-dicarboxylic acid 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 [2.2]paracyclophane-4,7-dicarboxylic acid dichloride
  参考文献：
  名称：

  Thermotropic Liquid Crystals from Planar Chiral Compounds: [2.2]Paracyclophane as a Mesogen Core

  摘要：

  New thermotropic mesomorphic compounds containing a [2.2]paracyclophane (PC) unit were synthesized and investigated (Scheme). Carboxylic acids were selected as the starting PC building blocks. The influence of structural features on the stability of the mesomorphic phases was studied (Figs. 1 and 2): for this purpose. the structures of the PC-carboxylate unit and the organic fragment of the aryl-ester moiety were varied systematically. Esters derived from PC-monocarboxylic acid did not exhibit liquid-crystalline (LC) properties, while diaryl PC-dicarboxylates favored mesomorphism. Dicarboxylate substituents arranged in the paraposition provided LC phases in a broad temperature range and considerably increased the mesomorphic interval in comparison with that of the structurally related pseudo-para PC derivatives.

  DOI：

  10.1002/1522-2675(200202)85:2<431::aid-hlca431>3.0.co;2-h
• 作为产物：
  描述：

  dimethyl[2.2]paracyclophane-4,7-dicarboxylate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以89%的产率得到[2.2]paracyclophane-4,7-dicarboxylic acid
  参考文献：
  名称：

  Thermotropic Liquid Crystals from Planar Chiral Compounds: [2.2]Paracyclophane as a Mesogen Core

  摘要：

  New thermotropic mesomorphic compounds containing a [2.2]paracyclophane (PC) unit were synthesized and investigated (Scheme). Carboxylic acids were selected as the starting PC building blocks. The influence of structural features on the stability of the mesomorphic phases was studied (Figs. 1 and 2): for this purpose. the structures of the PC-carboxylate unit and the organic fragment of the aryl-ester moiety were varied systematically. Esters derived from PC-monocarboxylic acid did not exhibit liquid-crystalline (LC) properties, while diaryl PC-dicarboxylates favored mesomorphism. Dicarboxylate substituents arranged in the paraposition provided LC phases in a broad temperature range and considerably increased the mesomorphic interval in comparison with that of the structurally related pseudo-para PC derivatives.

  DOI：

  10.1002/1522-2675(200202)85:2<431::aid-hlca431>3.0.co;2-h

文献信息

• Thermotropic Liquid Crystals from Planar Chiral Compounds: [2.2]Paracyclophane as a Mesogen Core
  作者：Valeria I. Rozenberg、Elena L. Popova、Henning Hopf

  DOI：10.1002/1522-2675(200202)85:2<431::aid-hlca431>3.0.co;2-h

  日期：2002.2

  New thermotropic mesomorphic compounds containing a [2.2]paracyclophane (PC) unit were synthesized and investigated (Scheme). Carboxylic acids were selected as the starting PC building blocks. The influence of structural features on the stability of the mesomorphic phases was studied (Figs. 1 and 2): for this purpose. the structures of the PC-carboxylate unit and the organic fragment of the aryl-ester moiety were varied systematically. Esters derived from PC-monocarboxylic acid did not exhibit liquid-crystalline (LC) properties, while diaryl PC-dicarboxylates favored mesomorphism. Dicarboxylate substituents arranged in the paraposition provided LC phases in a broad temperature range and considerably increased the mesomorphic interval in comparison with that of the structurally related pseudo-para PC derivatives.