1-<5-(phenylselanyl)pentyl>-2-(phenylsulfanyl)-1H-benzimidazole | 191542-45-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-<5-(phenylselanyl)pentyl>-2-(phenylsulfanyl)-1H-benzimidazole
• 英文别名: 1-(5-Phenylselanylpentyl)-2-phenylsulfanylbenzimidazole
• CAS: 191542-45-7
• 化学式: C₂₄H₂₄N₂SSe
• 分子量: 451.494
• InChiKey: CLEPVXRAVLAMNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<5-(phenylselanyl)pentyl>-2-(phenylsulfanyl)-1H-benzimidazole 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以17%的产率得到7,8,9,10-tetrahydro-6H-benzo[4,5]imidazo[1,2-a]azepine
  参考文献：
  名称：

  Radical cyclisation onto imidazoles and benzimidazoles

  摘要：

  A new protocol for the synthesis of [1, 2-a]-fused benzimidazoles and imidazoles has been developed using intramolecular homolytic aromatic substitution via omega-alkyl radicals generated from 1-(omega-benzeneselenylalkyl)- 2-(benzenesulfenyl)-benzimidazoles and -2-(p-toluenesulfonyl)imidozoles. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00740-5
• 作为产物：
  描述：

  1-(三苯基甲基)苯并咪唑 在 盐酸 、 正丁基锂 、 四甲基乙二胺 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 8.33h， 生成 1-<5-(phenylselanyl)pentyl>-2-(phenylsulfanyl)-1H-benzimidazole
  参考文献：
  名称：

  Radical cyclisation onto imidazoles and benzimidazoles

  摘要：

  New synthetic methodology has been developed for the synthesis of [1,2-a]Fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(omega-alkyl) radicals are generated using Bu3SnH from N-(omega-phenylselanyl)aIkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used as the leaving groups in the homolytic substitutions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00104-0

文献信息

• Radical cyclisation onto imidazoles and benzimidazoles
  作者：Fawaz Aldabbagh、W.Russell Bowman

  DOI：10.1016/s0040-4020(99)00104-0

  日期：1999.3

  New synthetic methodology has been developed for the synthesis of [1,2-a]Fused imidazoles and benzimidazoles using intramolecular homolytic aromatic substitution. In the intramolecular substitution, N-(omega-alkyl) radicals are generated using Bu3SnH from N-(omega-phenylselanyl)aIkyl side chains. Phenylselanyl groups are used as radical leaving groups to avoid problems in the N-alkylation of imidazoles and benzimidazoles. Arylsulfones for imidazoles, and phenylsulfides for benzimidazoles, are used as the leaving groups in the homolytic substitutions. (C) 1999 Elsevier Science Ltd. All rights reserved.