(S)-tert-butyl 1-(2,6-dibromophenyl)-3-phenylpropan-2-ylcarbamate | 1142923-80-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-tert-butyl 1-(2,6-dibromophenyl)-3-phenylpropan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S)-1-(2,6-dibromophenyl)-3-phenylpropan-2-yl]carbamate
• CAS: 1142923-80-5
• 化学式: C₂₀H₂₃Br₂NO₂
• 分子量: 469.216
• InChiKey: MCEVWSYIMHHLTP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 1-(2,6-dibromophenyl)-3-phenylpropan-2-ylcarbamate 在 DPE-Phos 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines

  摘要：

  Stabilized ortho-bromo phenyllithium reagents, generated via lithium-halogen exchange of aryl iodides, undergo regioselective ring opening of mono-substituted N-Boc, N-Cbz, and N-tosyl-protected aziridines in good to excellent yields. The resulting ortho-bromo phenethylamines can be cyclized under transition-metal-catalyzed conditions to give 2-substituted chiral, non-racemic indolines in good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.047
• 作为产物：
  描述：

  1,3-二溴-2-碘苯 、 tert-butyl (S)-2-benzylaziridine-1-carboxylate 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 2.5h， 以87%的产率得到(S)-tert-butyl 1-(2,6-dibromophenyl)-3-phenylpropan-2-ylcarbamate
  参考文献：
  名称：

  Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines

  摘要：

  Stabilized ortho-bromo phenyllithium reagents, generated via lithium-halogen exchange of aryl iodides, undergo regioselective ring opening of mono-substituted N-Boc, N-Cbz, and N-tosyl-protected aziridines in good to excellent yields. The resulting ortho-bromo phenethylamines can be cyclized under transition-metal-catalyzed conditions to give 2-substituted chiral, non-racemic indolines in good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.047

文献信息

• Ring opening of aziridines with ortho-bromophenyl metal reagents: synthesis of 2-substituted indolines
  作者：David J. Michaelis、Thomas A. Dineen

  DOI：10.1016/j.tetlet.2009.02.047

  日期：2009.4

  Stabilized ortho-bromo phenyllithium reagents, generated via lithium-halogen exchange of aryl iodides, undergo regioselective ring opening of mono-substituted N-Boc, N-Cbz, and N-tosyl-protected aziridines in good to excellent yields. The resulting ortho-bromo phenethylamines can be cyclized under transition-metal-catalyzed conditions to give 2-substituted chiral, non-racemic indolines in good yields. (C) 2009 Elsevier Ltd. All rights reserved.