2-(1H-benzimidazol-2-yl)-3-(p-methylphenyl)-propionitrile | 63052-13-1

• 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: 2-(1H-benzimidazol-2-yl)-3-(p-methylphenyl)-propionitrile
• 英文别名: 2-(1H-benzoimidazol-2-yl)-3-p-tolyl-propionitrile；2-(1H-benzimidazol-2-yl)-3-(4-methylphenyl)propanenitrile
• CAS: 63052-13-1
• 化学式: C₁₇H₁₅N₃
• 分子量: 261.326
• InChiKey: AUNMEPSEXUNWQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 2-(1H-benzimidazol-2-yl)-3-(p-methylphenyl)-propionitrile 在 苄基三乙基氯化铵 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 3.0h， 以75%的产率得到2-(1-methyl-1H-benzimidazol-2-yl)-3-(p-methylphenyl)-propionitrile
  参考文献：
  名称：

  Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

  摘要：

  Condensation of (1H-benzimidazole-2-yl)-acetonitrile 1 with aromatic aldehydes in 5% NaOH solution gave the corresponding 2-(1H-benzimidazole-2-yl)3-aryl-acrylonitrile 2, which on treatment with NaBH4 in ethanol unexpectedly gave 2-(1H-benzimidazole-2-yl)-3-aryl-propionitrile 3 by the regiospecific reduction of the double bond. Shaking a solution of 2 with H-2/Pd-C in methanol also gave 3. Reaction of 2 with DMS gave the corresponding N-methylated analogue 5, which also with NaBH4 gave 6, once again by the regiospecific reduction of the double bond as in the case of 1-demethylated analogue ( i. e., 2).

  DOI：

  10.1080/00397910701397177
• 作为产物：
  描述：

  2-氰甲基苯并咪唑 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 2-(1H-benzimidazol-2-yl)-3-(p-methylphenyl)-propionitrile
  参考文献：
  名称：

  Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile

  摘要：

  Condensation of (1H-benzimidazole-2-yl)-acetonitrile 1 with aromatic aldehydes in 5% NaOH solution gave the corresponding 2-(1H-benzimidazole-2-yl)3-aryl-acrylonitrile 2, which on treatment with NaBH4 in ethanol unexpectedly gave 2-(1H-benzimidazole-2-yl)-3-aryl-propionitrile 3 by the regiospecific reduction of the double bond. Shaking a solution of 2 with H-2/Pd-C in methanol also gave 3. Reaction of 2 with DMS gave the corresponding N-methylated analogue 5, which also with NaBH4 gave 6, once again by the regiospecific reduction of the double bond as in the case of 1-demethylated analogue ( i. e., 2).

  DOI：

  10.1080/00397910701397177

文献信息

• HAMMAD M.; EMRAN A., Z. NATURFORSCH. <ZENB-AX>, 1977, 32B, NO 3, 304-306
  作者：HAMMAD M.、 EMRAN A.

  DOI：——

  日期：——