(2R)-N,N-dibenzyl-2-bromo-4-methylpentan-1-amine | 324047-76-9

• 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: (2R)-N,N-dibenzyl-2-bromo-4-methylpentan-1-amine
• CAS: 324047-76-9
• 化学式: C₂₀H₂₆BrN
• 分子量: 360.337
• InChiKey: DUEZVJBYMUOQLL-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-N,N-dibenzyl-2-bromo-4-methylpentan-1-amine 、 (S)-2-((S)-2-Amino-3-methyl-pentylamino)-3-methyl-pentan-1-ol 在 cesium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以46%的产率得到(S)-2-[(S)-2-((S)-2-Dibenzylamino-4-methyl-pentylamino)-3-methyl-pentylamino]-3-methyl-pentan-1-ol
  参考文献：
  名称：

  CsOH-promoted chemoselective mono-N-alkylation of diamines and polyamines

  摘要：

  Selective N-alkylation of diamines and polyamines was carried out using cesium hydroxide, 4 Angstrom molecular sieves, and DMF. This protocol was highly chemoselective, favoring mono-N-alkylation over overalkylations. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01747-0
• 作为产物：
  描述：

  (S)-(+)-2-(N,N-二苄基氨基)-4-甲基戊醇 在 N,N-二甲基甲酰胺 二溴亚砜 作用下， 以 环己烷 为溶剂， 反应 3.0h， 以93%的产率得到(2R)-N,N-dibenzyl-2-bromo-4-methylpentan-1-amine
  参考文献：
  名称：

  Efficient synthesis of β-amino bromides

  摘要：

  beta-Aminoalcohols were smoothly converted to beta-amino bromides using thionyl bromide and DME which were easily isolated without any further purification. Participation by the beta-amino group in brominations not only enhanced reaction rates but also promoted stereo- and regioselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00330-0

文献信息

• Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI
  作者：Ralph N Salvatore、Feixia Chu、Advait S Nagle、Elona A Kapxhiu、Richard M Cross、Kyung Woon Jung

  DOI：10.1016/s0040-4020(02)00286-7

  日期：2002.4

  Novel solution and solid-phase methods for the synthesis of carbonates and carbamates were developed using cesium bases and TBAI via a three-component coupling. Cesium carbonate not only promoted successful carbonylations of alcohols and carbamations of amines, but also suppressed common side reactions traditionally seen using existing protocols. Various alcohols and amines were examined, using a wide

  利用铯碱和TBAI，通过三组分偶联，开发了用于合成碳酸盐和氨基甲酸酯的新型溶液和固相方法。碳酸铯不仅可以促进醇的成功羰基化和胺的氨基甲酸酯化，而且还可以抑制传统上使用现有方案观察到的常见副反应。使用各种各样的烷基卤化物检查了各种醇和胺，结果表明该方法具有高度的化学选择性。特别地，使用对空间有要求的底物或氨基酸衍生物只能提供相应的产物，从而提供了广泛的应用，例如新颖的保护基和拟肽合成。
• Efficient Carbamate Synthesis via a Three-Component Coupling of an Amine, CO₂, and Alkyl Halides in the Presence of Cs₂CO₃ and Tetrabutylammonium Iodide
  作者：Ralph N. Salvatore、Seung Il Shin、Advait S. Nagle、Kyung Woon Jung

  DOI：10.1021/jo001140u

  日期：2001.2.1
• Efficient synthesis of β-amino bromides
  作者：Advait S Nagle、Ralph N Salvatore、Byong-Don Chong、Kyung Woon Jung

  DOI：10.1016/s0040-4039(00)00330-0

  日期：2000.4

  beta-Aminoalcohols were smoothly converted to beta-amino bromides using thionyl bromide and DME which were easily isolated without any further purification. Participation by the beta-amino group in brominations not only enhanced reaction rates but also promoted stereo- and regioselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.
• CsOH-promoted chemoselective mono-N-alkylation of diamines and polyamines
  作者：Ralph N Salvatore、Shaun E Schmidt、Seung Il Shin、Advait S Nagle、Jay H Worrell、Kyung Woon Jung

  DOI：10.1016/s0040-4039(00)01747-0

  日期：2000.12

  Selective N-alkylation of diamines and polyamines was carried out using cesium hydroxide, 4 Angstrom molecular sieves, and DMF. This protocol was highly chemoselective, favoring mono-N-alkylation over overalkylations. (C) 2000 Published by Elsevier Science Ltd.