5-(4-Heptylphenyl)-1-benzothiophene-2-carboxamide | 331834-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5-(4-Heptylphenyl)-1-benzothiophene-2-carboxamide
• CAS: 331834-20-9
• 化学式: C₂₂H₂₅NOS
• 分子量: 351.513
• InChiKey: RZCUZOOXDPKAMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-Heptylphenyl)-1-benzothiophene-2-carboxamide 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以43%的产率得到2-cyano-5-(4-heptylphenyl)-1-benzothiophene
  参考文献：
  名称：

  摘要：

  The synthesis and transition temperatures are reported for several 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans, 2-(4'-alkylbiphenyl-4-yl)-5-cyano- and 5-(4'-alkylbiphenyl-4-yl)-2-cyano-1-benzofurans, and for compounds with other combinations of terminal alkyl and cyano groups in 2,5-disubstituted-1-benzofurans containing two phenyl units; some isolated examples of related cyclohexane systems are also presented. The mesogenic behaviour of these compounds and several intermediates (e.g. amides, acids and esters) is discussed and the transition temperatures are rationalised on the following basis (a) 1-benzofuran is a superior core unit to benzene, (b) 2,5-disubstitution in 1-benzofuran gives a bent core which adversely affects mesogenicity, to an extent which depends on its position in the core, (c) antiparallel associations in terminal cyano compounds can eliminate the disadvantage of a bent core structure, (d) 2-aryl-1-benzofurans have negligible inter-annular twist but 5-aryl-1-benzofurans have similar inter-annular twist to that in biphenyls.

  DOI：

  10.1039/b102837p
• 作为产物：
  描述：

  5-(4-Heptylphenyl)-1-benzothiophene 在 正丁基锂 、 氯化亚砜 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 5-(4-Heptylphenyl)-1-benzothiophene-2-carboxamide
  参考文献：
  名称：

  摘要：

  The synthesis and transition temperatures are reported for several 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans, 2-(4'-alkylbiphenyl-4-yl)-5-cyano- and 5-(4'-alkylbiphenyl-4-yl)-2-cyano-1-benzofurans, and for compounds with other combinations of terminal alkyl and cyano groups in 2,5-disubstituted-1-benzofurans containing two phenyl units; some isolated examples of related cyclohexane systems are also presented. The mesogenic behaviour of these compounds and several intermediates (e.g. amides, acids and esters) is discussed and the transition temperatures are rationalised on the following basis (a) 1-benzofuran is a superior core unit to benzene, (b) 2,5-disubstitution in 1-benzofuran gives a bent core which adversely affects mesogenicity, to an extent which depends on its position in the core, (c) antiparallel associations in terminal cyano compounds can eliminate the disadvantage of a bent core structure, (d) 2-aryl-1-benzofurans have negligible inter-annular twist but 5-aryl-1-benzofurans have similar inter-annular twist to that in biphenyls.

  DOI：

  10.1039/b102837p