(E)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate | 1580471-19-7

• 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: (E)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate
• CAS: 1580471-19-7
• 化学式: C₂₆H₃₉NO₅Si
• 分子量: 473.685
• InChiKey: LHNBGKUDCMYPDZ-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到(E)-tert-butyl 2-(3-ethoxy-3-oxoprop-1-en-1-yl)-3-(2-hydroxyethyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Highly Asymmetric Bromocyclization of Tryptophol: Unexpected Accelerating Effect of DABCO-Derived Bromine Complex

  摘要：

  Highly asymmetric bromocyclization of tryptophol by using chiral anionic phase-transfer catalyst and DABCO-derived brominating reagent is described. Optimization of the reaction conditions revealed that the reaction rate was accelerated together with improvement of enantioselectivity by addition of catalytic DABCO-derived brominating reagent. From tryptophol, 3-bromofuroindoline could be directly obtained in excellent enantioselectivities by employing this novel methodology.

  DOI：

  10.1021/ol5004109
• 作为产物：
  描述：

  tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole-1-carboxylate 、 丙烯酸乙酯 在 过氧化苯甲酸叔丁酯 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 17.0h， 以2.52 g的产率得到(E)-tert-butyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-(3-ethoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Highly Asymmetric Bromocyclization of Tryptophol: Unexpected Accelerating Effect of DABCO-Derived Bromine Complex

  摘要：

  Highly asymmetric bromocyclization of tryptophol by using chiral anionic phase-transfer catalyst and DABCO-derived brominating reagent is described. Optimization of the reaction conditions revealed that the reaction rate was accelerated together with improvement of enantioselectivity by addition of catalytic DABCO-derived brominating reagent. From tryptophol, 3-bromofuroindoline could be directly obtained in excellent enantioselectivities by employing this novel methodology.

  DOI：

  10.1021/ol5004109