5-Bromo-2-(4-pentyl-phenyl)-benzofuran | 331834-00-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-Bromo-2-(4-pentyl-phenyl)-benzofuran
• 英文别名: 5-Bromo-2-(4-pentylphenyl)-1-benzofuran
• CAS: 331834-00-5
• 化学式: C₁₉H₁₉BrO
• 分子量: 343.263
• InChiKey: SMNKHVAGKQHIIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氰基苯硼酸 、 5-Bromo-2-(4-pentyl-phenyl)-benzofuran 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以12%的产率得到5-(4-cyanophenyl)-2-(4-pentylphenyl)-1-benzofuran
  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：

  1-溴-4-(2,2-二甲氧基乙氧基)苯 在 四(三苯基膦)钯 、 PPA 、 sodium carbonate 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 、 乙醚 、 正己烷 、 氯苯 为溶剂， 反应 2.0h， 生成 5-Bromo-2-(4-pentyl-phenyl)-benzofuran
  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