(S,S)-N-sec-butyl-α-phenylethylamine | 86013-68-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S,S)-N-sec-butyl-α-phenylethylamine
• 英文别名: (2S)-N-((S)-1-phenylethyl)butan-2-amine；sek.-Butyl-phenylaethyl-amin；(2S)-N-[(1S)-1-phenylethyl]butan-2-amine
• CAS: 86013-68-5
• 化学式: C₁₂H₁₉N
• 分子量: 177.29
• InChiKey: PXWVXIBJJNDWLW-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  [1-Methyl-prop-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 在 diborane(6) 作用下， 以 四氢呋喃 为溶剂， 生成 (S,S)-N-sec-butyl-α-phenylethylamine
  参考文献：
  名称：

  Charles,J.-P. et al., Bulletin de la Societe Chimique de France, 1970, p. 4439 - 4446

  摘要：

  DOI：

文献信息

• A Simple Diastereoselective Synthesis of Chiral Nonracemic Aliphatic Amines
  作者：G. V. Grishina、E. R. Luk’yanenko、A. A. Borisenko

  DOI：10.1007/s11178-005-0248-1

  日期：2005.6

  An efficient procedure has been developed for the diastereoselective synthesis of chiral aliphatic amines (diastereoisomeric excess >96%) from (1S)-N-(1-methylethylidene)-1-phenylethylamine, i.e., Schiff base derived from the simplest ketone (acetone) and (1S)-1-phenylethylamine. The procedure includes successive lithiation, alkylation, and reduction and is characterized by high regioselectivity in the formation of alkylated syn-Z-imines. Hydride reduction of the prochiral C=N bond in the latter gives mainly optically active aliphatic amines with R configuration. All reactions are performed as a one-pot process without isolation of intermediate products.

  开发了一种有效的方法，用于从 (1S)-N-(1-甲基亚乙基)-1-苯乙胺（即源自最简单的酮（丙酮）的席夫碱）非对映选择性合成手性脂肪胺（非对映异构体过量 >96%）和(1S)-1-苯乙胺。该过程包括连续的锂化、烷基化和还原，其特点是在烷基化顺式-Z-亚胺的形成中具有高区域选择性。后者的前手性 C=N 键的氢化物还原主要产生具有 R 构型的光学活性脂肪胺。所有反应均以一锅法进行，无需分离中间产物。
• Catalytic alkyl group exchange reaction of primary and secondary amines
  作者：Shunichi Murahashi、Noriaki Yoshimura、Tatsuo Tsumiyama、Takeyuki Kojima

  DOI：10.1021/ja00353a025

  日期：1983.7
• Ytterbium Acetate Promoted Asymmetric Reductive Amination:  Significantly Enhanced Stereoselectivity
  作者：Thomas C. Nugent、Mohamed El-Shazly、Vijay N. Wakchaure

  DOI：10.1021/jo7021235

  日期：2008.2.1

  Reductive amination of prochiral unhindered 2-alkanones 1 with (R)- or (S)-alpha-MBA in the presence of Yb(OAc)(3) (50-110 mol %), Raney-Ni, and hydrogen (120 psi) results in increased diastereoselectivity for the amine products 2 (80-89% de) with good yield (80-87%). The increased de is based on comparison with the best previously reported de's when using (R)- or (S)-alpha-MBA, regardless of the strategy employed [stepwise (isolation of ketimines) or one-pot (reductive amination)], reducing agent examined, or achiral Lewis acid or Bronsted acid examined. An in situ cis- to trans-ketimine isomerization mechanism, promoted by Yb(OAC)(3), has been proposed to account for the observed increase in diastereoselectivity and suggests a new entry into the control of ketimine geometry.