1,2-diphenyl-N-((R)-1-phenylethyl)ethylamine | 1034088-55-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-diphenyl-N-((R)-1-phenylethyl)ethylamine
• 英文别名: 1,2-diphenyl-N-[(1R)-1-phenylethyl]ethanamine
• CAS: 1034088-55-5
• 化学式: C₂₂H₂₃N
• 分子量: 301.431
• InChiKey: JAQGHUIEZAQUHM-ZZWBGTBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 溴甲苯 、 苯甲醛 在 三氟乙酸 、 锌 作用下， 以 乙腈 为溶剂， 反应 1.67h， 以82%的产率得到1,2-diphenyl-N-((R)-1-phenylethyl)ethylamine
  参考文献：
  名称：

  Chiral amines in the diastereoselective Mannich-related multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines, and β-arylethylamines

  摘要：

  The multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines and beta-arylethylamines has been undergone starting from aryl- or benzylzinc reagents, aldehydes, and primary or secondary chiral amines. Good to high diastereoselectivities have been obtained from both L-proline ester derivatives 1 and (+/-)-trans-1-allyl-2,5-dimethylpiperazine (4). The use of R-(+)-1-phenylethylamine (7) provides important diastereoisomeric excesses (similar to 60%) in conjunction with very high chemical yields. This work constitutes a preliminary entry to the intended development of a more flexible reaction system, involving easily cleavable chiral amines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.058

文献信息

• Pyrimidopteridine-Catalyzed Hydroamination of Stilbenes with Primary Amines: A Dual Photoredox and Hydrogen Atom Transfer Catalyst
  作者：Tobias Taeufer、Richy Hauptmann、Firas El-Hage、Thea S. Mayer、Haijun Jiao、Jabor Rabeah、Jola Pospech

  DOI：10.1021/acscatal.0c05540

  日期：2021.4.16

  potent organic pyrimidopteridine photoredox catalyst (E*[PrPPT*/PrPPT·–] = +2.10 V vs SCE in MeCN), the photo-mediated hydroamination of stilbenes was enabled using unprotected, primary aliphatic, allylic, benzylic amines for the synthesis of various α-phenyl phenethylamine derivatives. Notably, the stereogenic center of α-chiral amines was fully preserved. Both starting materials serve as competent quenching

  描述了杂芳族光氧化还原催化剂在无添加剂的丁苯酯的光介导的氢化胺化中的适用性。由高效有机嘧啶蝶啶光氧化还原催化剂（E * [ PrPPT * / PrPPT · –] ＝ + 2.10V相对于MeCN中的SCE），使用未保护的伯脂族烯丙基烯丙基苄基胺来合成各种α-苯基苯乙胺衍生物，从而实现了对苯乙烯的光介导的氢化胺化。值得注意的是，α-手性胺的立体中心完全被保留。两种起始材料都可以作为有效的淬火伙伴。荧光和竞争性荧光猝灭实验以及电子顺磁共振波谱分析和密度泛函理论计算可以推论出合理的反应机理。
• Three-Component Synthesis of α-Branched Amines under Barbier-like Conditions
  作者：Erwan Le Gall、Caroline Haurena、Stéphane Sengmany、Thierry Martens、Michel Troupel

  DOI：10.1021/jo901704s

  日期：2009.10.16

  An array of alpha-branched amines has been prepared by using an expedient three-component Mannich-type reaction among organic halides, aldehyde derivatives, and amines. The experimental procedure, which is characterized by its simplicity, employs zinc dust for the in situ generation of organozinc reagents. We show that this Barbier-like protocol constitutes a useful entry to diaryl-methylamines, 1,2-diarylethylamines, alpha- or beta-amino esters, benzylamines, and beta-arylethylamines.
• Chiral amines in the diastereoselective Mannich-related multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines, and β-arylethylamines
  作者：Caroline Haurena、Erwan LeGall、Stéphane Sengmany、Thierry Martens

  DOI：10.1016/j.tet.2010.10.058

  日期：2010.12

  The multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines and beta-arylethylamines has been undergone starting from aryl- or benzylzinc reagents, aldehydes, and primary or secondary chiral amines. Good to high diastereoselectivities have been obtained from both L-proline ester derivatives 1 and (+/-)-trans-1-allyl-2,5-dimethylpiperazine (4). The use of R-(+)-1-phenylethylamine (7) provides important diastereoisomeric excesses (similar to 60%) in conjunction with very high chemical yields. This work constitutes a preliminary entry to the intended development of a more flexible reaction system, involving easily cleavable chiral amines. (C) 2010 Elsevier Ltd. All rights reserved.