2-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)propanenitrile | 483334-01-6

• 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: 2-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)propanenitrile
• CAS: 483334-01-6
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: DPGRWSHUBYMKEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)propanenitrile 、 硫酸二甲酯 在 苄基三乙基氯化铵 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 3.17h， 以70%的产率得到3-(3,4-Dimethoxyphenyl)-2-(1-methylbenzimidazol-2-yl)propanenitrile
  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 4.33h， 生成 2-(1H-benzimidazol-2-yl)-3-(3,4-dimethoxyphenyl)propanenitrile
  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

• Unexpected Regiospecific Reduction of the Double Bond by NaBH₄ in 2‐(1‐Methyl/1H‐benzimidazole‐2‐yl)‐3‐aryl‐acrylonitrile
  作者：P. K. Dubey、P. V. V. Prasada Reddy

  DOI：10.1080/00397910701397177

  日期：2007.7.1

  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).