(E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-methylpyridin-2(1H)-ylidene]acetonitrile | 1381866-79-0

• 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: (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-methylpyridin-2(1H)-ylidene]acetonitrile
• 英文别名: (2E)-1H-benzimidazol-2-yl(1-methylpyridin-2(1H)-ylidene)ethanenitrile；(2E)-2-(1H-benzimidazol-2-yl)-2-(1-methylpyridin-2-ylidene)acetonitrile
• CAS: 1381866-79-0
• 化学式: C₁₅H₁₂N₄
• 分子量: 248.287
• InChiKey: LQQLOHLECZYMOM-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-methylpyridin-2(1H)-ylidene]acetonitrile 在 2'-溴-4-氯苯乙酮 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以70%的产率得到2-({1H-benzo[d]imidazol-2(3H)-ylidene}(cyano)methyl)-1-methylpyridinium bromide
  参考文献：
  名称：

  Mukaiyama reagents in the synthesis of (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)ylidene]acetonitriles and their further electronic rearrangements effected by the action of acids and alkylating agents

  摘要：

  Reactions of N-alkyl-2-chloropyridinium salts with benzimidazolylacetonitriles result in (E)-2-(1Hbenzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)-ylidene]acetonitriles. The alkylation of the latter with omega-bromoacetophenones in boiling acetone may gives rise to the N-alkylated salts, which are stabilized in two configurations, Z and E. The heating of the salts in acetonitrile causes their transformation into 2-(1H-benzo[d]-imidazol-2(3H)-ylidene(cyano)methyl)-1-methylpyridinium bromide due to the dearoylmethylation. The structure of the latter was proved by the XRD analysis.

  DOI：

  10.1134/s1070363212040238
• 作为产物：
  描述：

  2-氰甲基苯并咪唑 、 2-氯-1-甲基吡啶碘化物 在 三乙胺 作用下， 以52%的产率得到(E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-methylpyridin-2(1H)-ylidene]acetonitrile
  参考文献：
  名称：

  Mukaiyama reagents in the synthesis of (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)ylidene]acetonitriles and their further electronic rearrangements effected by the action of acids and alkylating agents

  摘要：

  Reactions of N-alkyl-2-chloropyridinium salts with benzimidazolylacetonitriles result in (E)-2-(1Hbenzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)-ylidene]acetonitriles. The alkylation of the latter with omega-bromoacetophenones in boiling acetone may gives rise to the N-alkylated salts, which are stabilized in two configurations, Z and E. The heating of the salts in acetonitrile causes their transformation into 2-(1H-benzo[d]-imidazol-2(3H)-ylidene(cyano)methyl)-1-methylpyridinium bromide due to the dearoylmethylation. The structure of the latter was proved by the XRD analysis.

  DOI：

  10.1134/s1070363212040238

文献信息

• Mukaiyama reagents in the synthesis of (E)-2-(1H-benzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)ylidene]acetonitriles and their further electronic rearrangements effected by the action of acids and alkylating agents
  作者：T. A. Saraeva、G. E. Khoroshilov、R. I. Zubatyuk、O. V. Shishkin

  DOI：10.1134/s1070363212040238

  日期：2012.4

  Reactions of N-alkyl-2-chloropyridinium salts with benzimidazolylacetonitriles result in (E)-2-(1Hbenzo[d]imidazol-2-yl)-2-[1-alkylpyridin-2(1H)-ylidene]acetonitriles. The alkylation of the latter with omega-bromoacetophenones in boiling acetone may gives rise to the N-alkylated salts, which are stabilized in two configurations, Z and E. The heating of the salts in acetonitrile causes their transformation into 2-(1H-benzo[d]-imidazol-2(3H)-ylidene(cyano)methyl)-1-methylpyridinium bromide due to the dearoylmethylation. The structure of the latter was proved by the XRD analysis.