1-<5-(phenylselanyl)pentyl>-2-tosyl-1H-imidazole | 191542-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-<5-(phenylselanyl)pentyl>-2-tosyl-1H-imidazole
• 英文别名: 2-(4-Methylphenyl)sulfonyl-1-(5-phenylselanylpentyl)imidazole
• CAS: 191542-42-4
• 化学式: C₂₁H₂₄N₂O₂SSe
• 分子量: 447.46
• InChiKey: BDECSRBKGGOSNX-UHFFFAOYSA-N

物化性质

• 沸点：
  601.6±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-<5-(phenylselanyl)pentyl>-2-tosyl-1H-imidazole 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以63%的产率得到6,7,8,9-四氢-5H-咪唑[1,2-a]氮杂卓
  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：

  对甲基苯磺酰氟 在 正丁基锂 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-<5-(phenylselanyl)pentyl>-2-tosyl-1H-imidazole
  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

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.