tert-butyl 3-(2-hydroxyethyl)-7-methoxy-1H-indole-1-carboxylate | 1580470-76-3

• 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: tert-butyl 3-(2-hydroxyethyl)-7-methoxy-1H-indole-1-carboxylate
• CAS: 1580470-76-3
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: WXQHSFYGEFDFPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  60.69
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-hydroxyethyl)-7-methoxy-1H-indole-1-carboxylate 在 C₁₅H₁₇F₆N₂⁽¹⁺⁾*Br₂*BF₄^(1-) 、 2C₁₅H₁₇F₆N₂⁽¹⁺⁾*3BF₄^(1-)*Br⁽¹⁺⁾ 、 (R)-1,1'-binaphthyl-2,2'-phosphoric acid 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以98%的产率得到(3aR,8aS)-tert-butyl 3a-bromo-7-methoxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-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：

  7-Methoxytryptophol 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 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 2.0h， 生成 tert-butyl 3-(2-hydroxyethyl)-7-methoxy-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