2-allyl-1,3-bis(ethoxycarbonyl)benzimidazoline | 144369-28-8

• 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-allyl-1,3-bis(ethoxycarbonyl)benzimidazoline
• 英文别名: diethyl 2-prop-2-enyl-2H-benzimidazole-1,3-dicarboxylate
• CAS: 144369-28-8
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: BPHHTEYMECZHPR-UHFFFAOYSA-N

物化性质

• 沸点：
  397.1±22.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯并咪唑 、 烯丙基三丁基锡 、 氯甲酸乙酯 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到2-allyl-1,3-bis(ethoxycarbonyl)benzimidazoline
  参考文献：
  名称：

  Allylation of azoles with allyltributyltin via unstable N-(alkoxycarbonyl)azolium salts

  摘要：

  The one-pot reactions of imidazoles with allyltributyltin in the presence of alkyl chloroformates gave 2-allyl-1,3-bis(alkoxycarbonyl)-4-imidazolines in good yields. The reactions of thiazoles and oxazoles also proceeded in a similar manner. The instability of the intermediary quaternary salts required the nucleophiles to be added simultaneously with the chloroformate. Therefore, the reaction was specific for allyltributyltin, since it doesn't react with the carbonyl group of chloroformates. The dihydro allyl adducts thus obtained were aromatized with potassium ferricyanide under basic conditions to afford the corresponding 2-allylazoles.

  DOI：

  10.1021/jo00085a020

文献信息

• Reaction of imidazoles with allyltributyltin in the presence of chloroformate
  作者：Takashi Itoh、Hiroshi Hasegawa、Kazuhiro Nagata、Mamiko Okada、Akio Ohsawa

  DOI：10.1016/s0040-4039(00)79104-0

  日期：1992.9

  The reaction of imidazoles with allyltributyltin in the presence of chloroformate gave 2-allyl-1,3-dialkoxycarbonyl-4-imidazolines in good yields. The addition products were aromatized with potassium ferricyanide under basic condition lo afford corresponding 2-allylimidazoles.
• Takashi Itoh, Hiroshi Hasegawa, Kazuhiro Nagata, Akio Ohsawa, J. Org. Chem, 59 (1994) N 6, S 1319-1325
  作者：Takashi Itoh, Hiroshi Hasegawa, Kazuhiro Nagata, Akio Ohsawa

  DOI：——

  日期：——