(R)-N,N-dibenzyl-4-methyl-1-(trimethylsilyl)-1-pentyn-3-amine | 828300-94-3

• 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: (R)-N,N-dibenzyl-4-methyl-1-(trimethylsilyl)-1-pentyn-3-amine
• 英文别名: (R)-N,N-dibenzyl-4-methyl-1-(trimethylsilyl)pent-1-yn-3-amine；(3R)-N,N-dibenzyl-4-methyl-1-trimethylsilylpent-1-yn-3-amine
• CAS: 828300-94-3
• 化学式: C₂₃H₃₁NSi
• 分子量: 349.591
• InChiKey: FGBIFJKRUIKLSP-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (R)-N,N-dibenzyl-4-methyl-1-(trimethylsilyl)-1-pentyn-3-amine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以93%的产率得到(R)-N,N-dibenzyl-4-methyl-1-pentyn-3-amine
  参考文献：
  名称：

  现成的不饱和催化的二芳基P，N配体。

  摘要：

  DOI：

  10.1002/anie.200461286
• 作为产物：
  描述：

  异丁醛 、 三甲基乙炔基硅 、 二苄胺 在 (-)-2-(2-(diphenylphosphino)naphthalen-1-yl)-1-(perfluorobenzyl)-4,5-diphenyl-1H-imidazole 、 copper(I) bromide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到(R)-N,N-dibenzyl-4-methyl-1-(trimethylsilyl)-1-pentyn-3-amine
  参考文献：
  名称：

  Design, Preparation, and Implementation of an Imidazole-Based Chiral Biaryl P,N-Ligand for Asymmetric Catalysis

  摘要：

  A new strategy for increasing the barrier to rotation in biaryls has been developed that allows for the incorporation of 5-membered aromatic heterocycles into chiral atropisomers. Using this concept, an imidazole-based biaryl P,N-ligand has been designed and prepared as a single enantiomer. This ligand perfonns exceptionally well in the enantioselective A(3)-coupling, demonstrating the potential of this new design element.

  DOI：

  10.1021/ja407689a

文献信息

• Enantioselective, Copper(I)-Catalyzed Three-Component Reaction for the Preparation of Propargylamines
  作者：Nina Gommermann、Christopher Koradin、Kurt Polborn、Paul Knochel

  DOI：10.1002/anie.200352578

  日期：2003.12.1
• Diastereofacial π-Stacking as an Approach To Access an Axially Chiral P,N-Ligand for Asymmetric Catalysis
  作者：Balaji V. Rokade、Patrick J. Guiry

  DOI：10.1021/acscatal.6b03427

  日期：2017.4.7

  A phosphino-imidazoline (PHIM) ligand possessing axial chirality is prepared in a straightforward five-step synthesis. Configurational stability around the chiral axis is achieved by the diastereofacial pi-stacking between the pentafluorophenyl and the naphthalene rings. In particular, access to enantiopure ligand (S,S,R-a)-2a was realized by fractional crystallization of the corresponding similar to 3:1 atropdiastereomeric mixture. The preliminary application of ligand (S,S,R-a)-UCD-PHIM showed excellent activities in the enantioselective copper-catalyzed A3 coupling (ee's up to 98.1% and yields up to 98%).