(E)-Methyl 3-bromo-2-isocyano-5-methyl-2-hexenoate | 162104-60-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-Methyl 3-bromo-2-isocyano-5-methyl-2-hexenoate
• 英文别名: methyl (E)-3-bromo-2-isocyano-5-methylhex-2-enoate
• CAS: 162104-60-1
• 化学式: C₉H₁₂BrNO₂
• 分子量: 246.104
• InChiKey: GHQTWTPKGJMXKG-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-Methyl 3-bromo-2-isocyano-5-methyl-2-hexenoate 在 硫化氢 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 5-isobutyl-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  A novel synthesis of methyl 5-substituted thiazole-4-carboxylates using 3-bromo-2-isocyanoacrylates (BICA)

  摘要：

  A novel synthetic method for methyl 5-substituted thiazole-4-carboxylates (5) by the reaction of methyl 3-substituted 3-bromo-2-isocyanoacrylates(BICA)(1) with hydrogen sulfide in the presence of triethylamine in N,N-dimethylformamide was explored, and the reaction mechanism was elucidated.

  DOI：

  10.1016/0040-4039(94)02186-f
• 作为产物：
  描述：

  (E)-Methyl 2-(formylamino)-5-methyl-2-hexenoate 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 三氯氧磷 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-Methyl 3-bromo-2-isocyano-5-methyl-2-hexenoate
  参考文献：
  名称：

  A Novel Synthesis of Methyl 1,5-Disubstituted Imidazole-4-carboxylates Using 3-Bromo-2-isocyanoacrylates (BICA)

  摘要：

  Methyl 1,5-disubstituted imidazole-4-carboxylates 1 were synthesised using methyl 3-substituted 3-bromo-2-isocyanoacrylates 3 (BICA), and the reaction mechanism was elucidated. Reactions of 3, which were prepared by bromination of 3-substituted 2-(formylamino)acrylates 6 followed by dehydration of the formylamino group, with a variety of primary amines gave imidazoles 1 in good overall yields. A mechanistic study suggested a Michael reaction of an amine with 3 followed by p-elimination of hydrogen bromide exclusively afforded (E)-N,3-disubstituted 3-amino-2-isocyanoacrylates 2. Geometric isomerization to (Z)-2 with a base and subsequent cyclization gave imidazoles 1.

  DOI：

  10.1021/jo00104a018