(1S,2S)-(+)-trans-2-<1-(p-Toluenesulfonyl)indol-3-yl>cyclopropanecarboxylic acid | 164713-49-9

• 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: (1S,2S)-(+)-trans-2-<1-(p-Toluenesulfonyl)indol-3-yl>cyclopropanecarboxylic acid
• 英文别名: (+)-(1S,2S)-2-(1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylic acid；(1S,2S)-2-[1-(4-methylphenyl)sulfonylindol-3-yl]cyclopropane-1-carboxylic acid
• CAS: 164713-49-9
• 化学式: C₁₉H₁₇NO₄S
• 分子量: 355.414
• InChiKey: QULGINCSDAENOB-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(+)-trans-2-<1-(p-Toluenesulfonyl)indol-3-yl>cyclopropanecarboxylic acid 、 苯甲醇 生成 (1S,2R)-(+)-trans-2-<1-(p-Toluenesulfonyl)indol-3-yl>-1-<(benzyloxycarbonyl)amino>cyclopropane
  参考文献：
  名称：

  Stereoselective Synthesis of trans-2-(Indol-3-yl)cyclopropylamines: Rigid Tryptamine Analogs

  摘要：

  A procedure for the preparation of trans-2-(indol-3-yl)cyclopropylamines is reported. The key step in the sequence is a stereoselective palladium-catalyzed cyclopropanation of the indole-3-acryloyl derivative of Oppolzer's chiral sultam (bornane[10,2]sultam) with diazomethane, following by the purification of the resulting diastereomeric cyclopropanated sultams by recrystallization. Base hydrolysis of the pure crystalline diastereomers gave the resolved indolylcyclopropane carboxylic acids. These could be converted into enantiomers of indolylcyclopropylamine by Curtius rearrangement, which did not affect the absolute configuration. In addition, single crystal X-ray erystallography of the cyclopropanated sultam was used to determine the absolute configuration of the intermediate indolylcyclopropanecarboxylic acid and thus to establish the configuration of the final compound.

  DOI：

  10.1021/jo00116a028
• 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 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 29.0h， 生成 (1S,2S)-(+)-trans-2-<1-(p-Toluenesulfonyl)indol-3-yl>cyclopropanecarboxylic acid
  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.
• Stereoselective Synthesis of trans-2-(Indol-3-yl)cyclopropylamines: Rigid Tryptamine Analogs
  作者：Suwanna Vangveravong、David E. Nichols

  DOI：10.1021/jo00116a028

  日期：1995.6

  A procedure for the preparation of trans-2-(indol-3-yl)cyclopropylamines is reported. The key step in the sequence is a stereoselective palladium-catalyzed cyclopropanation of the indole-3-acryloyl derivative of Oppolzer's chiral sultam (bornane[10,2]sultam) with diazomethane, following by the purification of the resulting diastereomeric cyclopropanated sultams by recrystallization. Base hydrolysis of the pure crystalline diastereomers gave the resolved indolylcyclopropane carboxylic acids. These could be converted into enantiomers of indolylcyclopropylamine by Curtius rearrangement, which did not affect the absolute configuration. In addition, single crystal X-ray erystallography of the cyclopropanated sultam was used to determine the absolute configuration of the intermediate indolylcyclopropanecarboxylic acid and thus to establish the configuration of the final compound.