(5R,6S)-tert-butyl 5-hydroxy-6-(3-nitrophenyl)-4-oxo-3-((S)-1-phenylethyl)-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate | 1431767-82-6

• 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: (5R,6S)-tert-butyl 5-hydroxy-6-(3-nitrophenyl)-4-oxo-3-((S)-1-phenylethyl)-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate
• CAS: 1431767-82-6
• 化学式: C₃₂H₃₃N₃O₆
• 分子量: 555.631
• InChiKey: GEQNRQVGFAALAD-AVBDLTBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  41.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  114.91
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (5S,6R)-tert-butyl 5-hydroxy-6-(3-nitrophenyl)-4-oxo-3-((S)-1-phenylethyl)-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate 、 (5R,6S)-tert-butyl 5-hydroxy-6-(3-nitrophenyl)-4-oxo-3-((S)-1-phenylethyl)-3,4,5,6-tetrahydro-1H-azocino[5,4-b]indole-7(2H)-carboxylate
  参考文献：
  名称：

  Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide

  摘要：

  We present here a synthetic route for the access to a series of diverse indoloazocine derivatives through selective epoxidation of chiral sulfonium salt 4, which reacts with diverse aromatic and aliphatic aldehydes to give trans-glycidic amides, followed by an intramolecular electrophilic aromatic substitution promoted by Cu(OTf)(2) giving the desired heterocyclic compound in a high chemical yield. Using this strategy, the total synthesis of (S,R)-(+)-norbalasubramide was achieved. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.068