2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-4-methyl-4-imidazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-4-methyl-4-imidazoline
• 英文别名: bis(1-chloroethyl) 4-methyl-2-prop-2-enyl-2H-imidazole-1,3-dicarboxylate
• 化学式: C₁₃H₁₈Cl₂N₂O₄
• 分子量: 337.203
• InChiKey: CUSWFOMMBDBLMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-4-methyl-4-imidazoline 在 氢氧化钾 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以57%的产率得到2-allyl-4-methylimidazole
  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
• 作为产物：
  描述：

  4-甲基咪唑 、 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 2.0h， 以82%的产率得到2-allyl-1,3-bis<(1-chloroethoxy)carbonyl>-4-methyl-4-imidazoline
  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

• 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：——
• 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.