(S)-(2-((2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl)(1-phenylethyl)amino)-2-oxoethyl)dimethylsulfonium bromide | 1431767-75-7

• 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: (S)-(2-((2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl)(1-phenylethyl)amino)-2-oxoethyl)dimethylsulfonium bromide
• 英文别名: dimethyl-[2-[2-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]ethyl-[(1S)-1-phenylethyl]amino]-2-oxoethyl]sulfanium;bromide
• CAS: 1431767-75-7
• 化学式: Br*C₂₇H₃₅N₂O₃S
• 分子量: 547.556
• InChiKey: KJVALZWLMQAXDA-BDQAORGHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(2-((2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl)(1-phenylethyl)amino)-2-oxoethyl)dimethylsulfonium bromide 在 copper(II) bis(trifluoromethanesulfonate) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (5S,6R)-tert-butyl 6-ethyl-5-hydroxy-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
• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 35.0h， 生成 (S)-(2-((2-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)ethyl)(1-phenylethyl)amino)-2-oxoethyl)dimethylsulfonium bromide
  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

文献信息

• Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide
  作者：Maira Juárez-Calderón、David M. Aparicio、Dino Gnecco、Jorge R. Juárez、Laura Orea、Angel Mendoza、Fernando Sartillo-Piscil、Esther del Olmo、Joel L. Terán

  DOI：10.1016/j.tetlet.2013.03.068

  日期：2013.5

  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.