(S)-1-methyl-3-((S)-1-phenylethyl)-dihydroindol-2-one | 865288-88-6

• 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: (S)-1-methyl-3-((S)-1-phenylethyl)-dihydroindol-2-one
• 英文别名: (3S)-3-methyl-1-[(1S)-1-phenylethyl]-3H-indol-2-one
• CAS: 865288-88-6
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: HUZZFBVEDHMHCY-STQMWFEESA-N

物化性质

• 沸点：
  430.5±44.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-methyl-3-((S)-1-phenylethyl)-dihydroindol-2-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 以95%的产率得到7-bromo-(1S)-methyl-3-((S)-1-phenylethyl)-dihydroindol-2-one
  参考文献：
  名称：

  Relaying Asymmetry of Transient Atropisomers of o-Iodoanilides by Radical Cyclizations

  摘要：

  Atropisomers of N-2 degrees -alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2 degrees -alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide.

  DOI：

  10.1021/ja055666d
• 作为产物：
  描述：

  1,2-二碘苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙基硼 、 氧气 、 三正丁基氢锡 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 N,N-二异丙基乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 60.0h， 生成 (S)-1-methyl-3-((S)-1-phenylethyl)-dihydroindol-2-one
  参考文献：
  名称：

  Relaying Asymmetry of Transient Atropisomers of o-Iodoanilides by Radical Cyclizations

  摘要：

  Atropisomers of N-2 degrees -alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2 degrees -alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide.

  DOI：

  10.1021/ja055666d

文献信息

• Relaying Asymmetry of Transient Atropisomers of <i>o</i>-Iodoanilides by Radical Cyclizations
  作者：Marc Petit、Andre J. B. Lapierre、Dennis P. Curran

  DOI：10.1021/ja055666d

  日期：2005.11.1

  Atropisomers of N-2 degrees -alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2 degrees -alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide.