Ethyl 2-formamido-5-(tert-butyldiphenylsilyl)pent-4-ynoate | 166655-25-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 2-formamido-5-(tert-butyldiphenylsilyl)pent-4-ynoate
• 英文别名: Ethyl 5-[tert-butyl(diphenyl)silyl]-2-formamidopent-4-ynoate
• CAS: 166655-25-0
• 化学式: C₂₄H₂₉NO₃Si
• 分子量: 407.585
• InChiKey: IRVJYILUPYQGIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-formamido-5-(tert-butyldiphenylsilyl)pent-4-ynoate 在 偶氮二异丁腈 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (E)-3,4-Dihydro-4-((tert-butyldiphenylsilyl)methylidene)-5-(ethylthio)-2H-pyrrole-2-carboxylic acid ethyl ester
  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
• 作为产物：
  描述：

  3-Bromoprop-1-ynyl-tert-butyl-diphenylsilane 在 盐酸 、 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 Ethyl 2-formamido-5-(tert-butyldiphenylsilyl)pent-4-ynoate
  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

文献信息

• Thiol Mediated Free Radical Cyclization of Alkenyl and Alkynyl Isocyanides
  作者：Mario D. Bachi、Anna Balanov、Nira Bar-Ner

  DOI：10.1021/jo00104a035

  日期：1994.12

  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.