(-)-Ethyl (E)-3--N-<2-(3-indolyl)ethyl>carbamoyl>prop-2-enoate | 157478-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (-)-Ethyl (E)-3--N-<2-(3-indolyl)ethyl>carbamoyl>prop-2-enoate
• 英文别名: ethyl (E)-4-[[(2S)-2-(hydroxymethyl)butyl]-[2-(1H-indol-3-yl)ethyl]amino]-4-oxobut-2-enoate
• CAS: 157478-96-1
• 化学式: C₂₁H₂₈N₂O₄
• 分子量: 372.464
• InChiKey: RKNWUJKJHVFZND-SCOAYWHSSA-N

物化性质

• 沸点：
  619.2±55.0 °C(predicted)
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-Ethyl (E)-3--N-<2-(3-indolyl)ethyl>carbamoyl>prop-2-enoate 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 20.0h， 生成 (+)-tacamonine
  参考文献：
  名称：

  Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization

  摘要：

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-{N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).

  DOI：

  10.1021/jo00097a037
• 作为产物：
  描述：

  (-)-(2S)-2-((tert-Butyldimethylsiloxy)methyl)butan-1-ol 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (-)-Ethyl (E)-3--N-<2-(3-indolyl)ethyl>carbamoyl>prop-2-enoate
  参考文献：
  名称：

  Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization

  摘要：

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-{N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).

  DOI：

  10.1021/jo00097a037

文献信息

• Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization
  作者：Masataka Ihara、Fumihito Setsu、Miyuki Shohda、Nobuaki Taniguchi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00097a037

  日期：1994.9

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).