(+/-)-trans-tert-butyl 2-(1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-trans-tert-butyl 2-(1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate
• 英文别名: tert-butyl (1R,2R)-2-[1-(4-methylphenyl)sulfonylindol-3-yl]cyclopropane-1-carboxylate
• 化学式: C₂₃H₂₅NO₄S
• 分子量: 411.522
• InChiKey: AOCUDNYYNXMDTQ-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(4-甲基苯基)磺酰]-1H-吲哚-3-甲醛 在 (S)-trans-Cl₂Ru(pybox-ip)(CH₂=CH₂) 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 17.0h， 生成 (+/-)-trans-tert-butyl 2-(1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines

  摘要：

  Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.

  DOI：

  10.1021/ol050790n

文献信息

• Catalytic Asymmetric Diazoacetate Cyclopropanation of 1-Tosyl-3-vinylindoles. A Route to Conformationally Restricted Homotryptamines
  作者：Lawrence R. Marcin、Derek J. Denhart、Ronald J. Mattson

  DOI：10.1021/ol050790n

  日期：2005.6.1

  Substituted 1-tosyl-3-vinylindoles undergo catalytic asymmetric cyclopropanation with ethyl- and tert-butyldiazoacetate to afford N-protected trans-2-(indol-3-yl)-1-cyclopropanecarboxylic esters in good yield and high enantiomeric excess (81-88% ee). The resulting cycloadducts are demonstrated to be useful intermediates for the synthesis of conformationally restricted, homotryptamine-like analogues such as BMS-505130.