2-Methyl-4,6-diphenyl-7-propyl-benzo[b]thiophene

• 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: 2-Methyl-4,6-diphenyl-7-propyl-benzo[b]thiophene
• 英文别名: 2-Methyl-4,6-diphenyl-7-propyl-1-benzothiophene
• 化学式: C₂₄H₂₂S
• 分子量: 342.505
• InChiKey: LRQPEMIPSSVOKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  反式-查耳酮 、 1-[1-(5-Methyl-thiophen-2-yl)-butyl]-1H-benzotriazole 在 正丁基锂 、 Amberlyst-15 acidic resin 作用下， 生成 2-Methyl-4,6-diphenyl-7-propyl-benzo[b]thiophene
  参考文献：
  名称：

  Efficient Syntheses of 2-Functionalized Thiophenes, Cyclopent[b]thiophenes, and Polysubstituted Benzo[b]thiophenes from 2-(Benzotriazol-1-ylmethyl)thiophenes

  摘要：

  Diverse 2-(functionalized-alkyl)- and 2-alkenylthiophenes 2a,b, 4a,b, and 6a-d are prepared via the side chain elaboration of 2-(benzotriazol-1-ylmethyl)thiophenes 3a,b, themselves readily available from the condensation of 1-(hydroxymethyl)benzotriazole with thiophenes 1a,b. Treatment of 2-(benzotriazol-1-ylmethyl)thiophenes 3b and 5gj with styrenes in the presence of zinc bromide results in formal [3 + 2] cycloaddition to give in good yields substituted cyclopent[b]thiophenes 16a/17a, 16b/17b, and 18. Lithiation and 1,4-addition to a variety of alpha,beta-unsaturated ketones and aldehydes, and subsequent acid-catalyzed intramolecular cyclization followed by debenzotriazolylation-dehydration converts 3 and 5 to a range of polysubstituted benzo[b]thiophenes 19a-d and 25a-e in moderate to excellent yields. NOE difference spectroscopy and NMR H-1-C-13 long-range correlation support structures of types 19 and 25 and exclude those of type 26, thus confirming the cyclization pathway.

  DOI：

  10.1021/jo970672g

文献信息

• Efficient Syntheses of 2-Functionalized Thiophenes, Cyclopent[<i>b</i>]thiophenes, and Polysubstituted Benzo[<i>b</i>]thiophenes from 2-(Benzotriazol-1-ylmethyl)thiophenes
  作者：Alan R. Katritzky、Larisa Serdyuk、Linghong Xie、Ion Ghiviriga

  DOI：10.1021/jo970672g

  日期：1997.9.1

  Diverse 2-(functionalized-alkyl)- and 2-alkenylthiophenes 2a,b, 4a,b, and 6a-d are prepared via the side chain elaboration of 2-(benzotriazol-1-ylmethyl)thiophenes 3a,b, themselves readily available from the condensation of 1-(hydroxymethyl)benzotriazole with thiophenes 1a,b. Treatment of 2-(benzotriazol-1-ylmethyl)thiophenes 3b and 5gj with styrenes in the presence of zinc bromide results in formal [3 + 2] cycloaddition to give in good yields substituted cyclopent[b]thiophenes 16a/17a, 16b/17b, and 18. Lithiation and 1,4-addition to a variety of alpha,beta-unsaturated ketones and aldehydes, and subsequent acid-catalyzed intramolecular cyclization followed by debenzotriazolylation-dehydration converts 3 and 5 to a range of polysubstituted benzo[b]thiophenes 19a-d and 25a-e in moderate to excellent yields. NOE difference spectroscopy and NMR H-1-C-13 long-range correlation support structures of types 19 and 25 and exclude those of type 26, thus confirming the cyclization pathway.