1-<3-(phenylselanyl)propyl>-1H-benzimidazole | 223928-08-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-<3-(phenylselanyl)propyl>-1H-benzimidazole
• 英文别名: 1-(3-Phenylselanylpropyl)benzimidazole
• CAS: 223928-08-3
• 化学式: C₁₆H₁₆N₂Se
• 分子量: 315.276
• InChiKey: SGESYDLWLHZBCI-UHFFFAOYSA-N

物化性质

• 沸点：
  459.0±51.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-<3-(phenylselanyl)propyl>-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 6.0h， 以5%的产率得到2,3-二氢-1H-吡咯并[1,2-A]苯并咪唑
  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
• 作为产物：
  描述：

  二苯基二硒醚 、 (9ci)-1-(3-氯丙基)-1H-苯并咪唑 在 sodium tetrahydroborate 作用下， 生成 1-<3-(phenylselanyl)propyl>-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.