(3aR,8aS)-allyl 3a-bromo-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate | 1580471-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3aR,8aS)-allyl 3a-bromo-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate
• 英文别名: allyl (3aR,8aS)-3a-bromo-2,3,3a,8a-tetrahydro-8H-furo[2,3-b]indole-8-carboxylate；prop-2-enyl (3aS,8bR)-8b-bromo-2,3a-dihydro-1H-furo[2,3-b]indole-4-carboxylate
• CAS: 1580471-26-6
• 化学式: C₁₄H₁₄BrNO₃
• 分子量: 324.174
• InChiKey: BOTOMIPRAVZSQD-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 C₁₅H₁₇F₆N₂⁽¹⁺⁾*Br₂*BF₄^(1-) 、 2C₁₅H₁₇F₆N₂⁽¹⁺⁾*3BF₄^(1-)*Br⁽¹⁺⁾ 、 四丁基氟化铵 、 (R)-1,1'-binaphthyl-2,2'-phosphoric acid 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 (3aR,8aS)-allyl 3a-bromo-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

文献信息

• Enantioselective Halocyclization of Indole Derivatives: Using 1,3-Dihalohydantoins with Anionic Chiral Co(III) Complexes
  作者：Ting-Ting Sun、Kun Liu、Shun-Xin Zhang、Jie Yu、Chun-Ru Wang、Chuan-Zhi Yao

  DOI：10.1055/a-1310-5213

  日期：2021.4

  Highly enantioselective halocyclization reactions of indole derivatives, including tryptophols and tryptamines, have been accomplished by means of anionic chiral Co(III) complexes and 1,3-dihalohydantoins (as little as 0.50 equiv). 3-Halo-fused indolines were obtained in excellent yields (up to 98%) and enantioselectivities (up to 98% ee), employing the chiral anion phase-transfer-catalysis strategy.

  摘要：利用阴离子手性Co（III）配合物和1,3-二卤代海因杜因（仅需0.50当量）实现了吲哚衍生物的高度对映选择性卤环化反应，包括色氨酸醇和色氨酸胺。采用手性阴离子相转移催化策略，得到了3-卤代融合吲哚烷，收率高（高达98％）和对映选择性高（高达98％ee）。