Ethyl 2-isocyano-5-methylhex-4-enoate | 166655-29-4

• 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: Ethyl 2-isocyano-5-methylhex-4-enoate
• CAS: 166655-29-4
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: FXBIZBFWARRJSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  Ethyl 2-isocyano-5-methylhex-4-enoate 、 乙硫醇 在 2-氨基-3-氯-1,4-萘醌 作用下， 以 甲苯 为溶剂， 反应 0.08h， 生成 5-Ethylsulfanyl-4-isopropyl-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Microwave assisted free radical cyclisation of alkenyl and alkynyl isocyanides with thiols

  摘要：

  Alkenyl and alkynyl isocyanides were synthesised and then reacted, using microwave flash-heating technology, with thiophenol, 2-mercaptoethanol and ethanethiol, in the presence of a radical initiator, to give highly functionalised pyrrolines and pyroglutamates. Direct comparison with results obtained using traditional heating techniques showed the advantage of using the microwave technology in terms of faster reactions and better yields. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)02888-5
• 作为产物：
  描述：

  ethyl 2-(diphenylmethyleneamino)-5-methylhex-4-enoate 在 盐酸 、 二异丙胺 、 三氯氧磷 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 Ethyl 2-isocyano-5-methylhex-4-enoate
  参考文献：
  名称：

  Thiol Mediated Free Radical Cyclization of Alkenyl and Alkynyl Isocyanides

  摘要：

  Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl- and 2-(arylthio)pyrrolines 11, 12, and 18. When 2-mercaptoethanol is used with the same isocyanides the reaction results in pyroglutamates 16, 17, or 19. These cyclizations involve the formation of a new carbon-carbon bond through intramolecular addition of a carbon-centered thioimidoyl radical to a carbon-carbon multiple bond. Although cyclic products are usually obtained in high yields, in a few cases a competing radical degradation process leading to isothiocyanates was observed. Isocyanide 8a carrying an allyl(phenyl) sulfide moiety isomerizes to 2-(phenylthio)pyrroline 24 in a series of sequential steps.

  DOI：

  10.1021/jo00104a035