2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-5-nitrobenzimidazoline | 144369-36-8

• 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<(1-chloroethoxy)carbonyl>-5-nitrobenzimidazoline
• 英文别名: bis(1-chloroethyl) 5-nitro-2-prop-2-enyl-2H-benzimidazole-1,3-dicarboxylate
• CAS: 144369-36-8
• 化学式: C₁₆H₁₇Cl₂N₃O₆
• 分子量: 418.233
• InChiKey: MTBKEDSMVLBBJN-UHFFFAOYSA-N

物化性质

• 沸点：
  517.3±50.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 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：
  105
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-硝基苯并咪唑 、 烯丙基三丁基锡 、 1-氯乙基氯甲酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 168.0h， 以87%的产率得到2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-5-nitrobenzimidazoline
  参考文献：
  名称：

  Reaction of imidazoles with allyltributyltin in the presence of chloroformate

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)79104-0

文献信息

• Allylation of azoles with allyltributyltin via unstable N-(alkoxycarbonyl)azolium salts
  作者：Takashi Itoh、Hiroshi Hasegawa、Kazuhiro Nagata、Akio Ohsawa

  DOI：10.1021/jo00085a020

  日期：1994.3

  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.
• 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：——