2-(1-苄基-5-硝基-1H-苯并[d]咪唑-4-基)乙腈 | 1007871-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(1-苄基-5-硝基-1H-苯并[d]咪唑-4-基)乙腈
• 英文名称: 2-(1-benzyl-5-nitro-1H-benzo[d]imidazol-4-yl)acetonitrile
• 英文别名: 2-(1-Benzyl-5-nitrobenzimidazol-4-yl)acetonitrile
• CAS: 1007871-92-2
• 化学式: C₁₆H₁₂N₄O₂
• 分子量: 292.297
• InChiKey: OCBASMPKQBWCLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  87.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-苄基-5-硝基-1H-苯并[d]咪唑-4-基)乙腈 在 硫酸 作用下， 反应 4.0h， 以90%的产率得到3-benzyl-3H-imidazo[4',5':3,4]benzo[c]isoxazole-8-carboxamide
  参考文献：
  名称：

  Sulfuric Acid Mediated Heterocyclization of ortho-Cyanomethylnitroarenes to Benzo[c]isoxazoles and Fused Benzo[c]isoxazoles

  摘要：

  The vicarious nucleophilic substitution of hydrogen (VNS) is used as the key step to convert substituted 5-nitrobenzimidazoles 1a-b into their ortho-cyanomethyl derivatives 2a-b. Conc. sulfuric acid mediated heterocyclization of these intermediates gave the novel 3H-imidazo[4',5':3,4]benzo[c]isoxazole-8-carboxamides 3a-b. To generalize this synthetic strategy for benzo[c]isoxazoles syntheses, the VNS products of para-substituted nitrobenzene 4a-d were successfully converted to the new benzo[c]isoxazoles derivatives 5a-d.

  DOI：

  10.3987/com-07-11148
• 作为产物：
  描述：

  4-氯苯氧基乙腈 、 1-苄基-5-硝基-1H-1,3-苯并咪唑 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以72%的产率得到2-(1-苄基-5-硝基-1H-苯并[d]咪唑-4-基)乙腈
  参考文献：
  名称：

  Sulfuric Acid Mediated Heterocyclization of ortho-Cyanomethylnitroarenes to Benzo[c]isoxazoles and Fused Benzo[c]isoxazoles

  摘要：

  The vicarious nucleophilic substitution of hydrogen (VNS) is used as the key step to convert substituted 5-nitrobenzimidazoles 1a-b into their ortho-cyanomethyl derivatives 2a-b. Conc. sulfuric acid mediated heterocyclization of these intermediates gave the novel 3H-imidazo[4',5':3,4]benzo[c]isoxazole-8-carboxamides 3a-b. To generalize this synthetic strategy for benzo[c]isoxazoles syntheses, the VNS products of para-substituted nitrobenzene 4a-d were successfully converted to the new benzo[c]isoxazoles derivatives 5a-d.

  DOI：

  10.3987/com-07-11148

文献信息

• Sulfuric Acid Mediated Heterocyclization of ortho-Cyanomethylnitroarenes to Benzo[c]isoxazoles and Fused Benzo[c]isoxazoles
  作者：Mehdi Bakavoli、Mehdi Pordel、Mohammad Rahimizadeh、Pooneh Jahandari、Esmaeel Rezaei Seresht

  DOI：10.3987/com-07-11148

  日期：——

  The vicarious nucleophilic substitution of hydrogen (VNS) is used as the key step to convert substituted 5-nitrobenzimidazoles 1a-b into their ortho-cyanomethyl derivatives 2a-b. Conc. sulfuric acid mediated heterocyclization of these intermediates gave the novel 3H-imidazo[4',5':3,4]benzo[c]isoxazole-8-carboxamides 3a-b. To generalize this synthetic strategy for benzo[c]isoxazoles syntheses, the VNS products of para-substituted nitrobenzene 4a-d were successfully converted to the new benzo[c]isoxazoles derivatives 5a-d.