2-((1-methylbenzimidazol-2-yl)thio)-3-phenylacrylonitrile | 57320-01-1

• 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-((1-methylbenzimidazol-2-yl)thio)-3-phenylacrylonitrile
• 英文别名: 2-(1-Methylbenzimidazol-2-yl)sulfanyl-3-phenylprop-2-enenitrile
• CAS: 57320-01-1
• 化学式: C₁₇H₁₃N₃S
• 分子量: 291.376
• InChiKey: BQEPUBRTNOHKQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  盐酸胍 、 2-((1-methylbenzimidazol-2-yl)thio)-3-phenylacrylonitrile 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 5-((1-methylbenzimidazol-2-yl)thio)-4-amino-6-phenylpyrimidine-2-amine
  参考文献：
  名称：

  Utility of Nitrogen Nucleophiles: a Simple Route for the Synthesis of 2-Substituted Benzimidazolylpyrimidines

  摘要：

  An efficient and simple route for the synthesis of 2-substituted benzimidazolylpyrimidines 5a-i has been developed from benzimidazolylunsaturated nitriles 2 using nitrogen nucleophiles. Treatment of 2 with thiourea/urea/guanidine hydrochloride in aq. KOH under reflux for 30min gave 3, which on further alkylation with an alkylating agent under PTC conditions gave 5a-i. Alternatively 5a-i could also be prepared by treatment of 2 with an alkylating agent under PTC conditions followed by treatment with thiourea /urea/guanidine hydrochloride in aq. KOH for 30min.

  DOI：

  10.1080/10426507.2014.947409
• 作为产物：
  描述：

  (1H-苯并[d]咪唑-2-基硫代)-乙腈 在 哌啶 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 2-((1-methylbenzimidazol-2-yl)thio)-3-phenylacrylonitrile
  参考文献：
  名称：

  Utility of Nitrogen Nucleophiles: a Simple Route for the Synthesis of 2-Substituted Benzimidazolylpyrimidines

  摘要：

  An efficient and simple route for the synthesis of 2-substituted benzimidazolylpyrimidines 5a-i has been developed from benzimidazolylunsaturated nitriles 2 using nitrogen nucleophiles. Treatment of 2 with thiourea/urea/guanidine hydrochloride in aq. KOH under reflux for 30min gave 3, which on further alkylation with an alkylating agent under PTC conditions gave 5a-i. Alternatively 5a-i could also be prepared by treatment of 2 with an alkylating agent under PTC conditions followed by treatment with thiourea /urea/guanidine hydrochloride in aq. KOH for 30min.

  DOI：

  10.1080/10426507.2014.947409