(1S,2R)-2-Benzyloxy-1-methyl-2-phenyl-ethylamine

• 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: (1S,2R)-2-Benzyloxy-1-methyl-2-phenyl-ethylamine
• 英文别名: (1R,2S)-1-phenyl-1-phenylmethoxypropan-2-amine
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: MPRLZANZNFLPCY-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-Benzyloxy-1-methyl-2-phenyl-ethylamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  手性C 2对称DMEU衍生物介导的1-四氢萘酮烯醇锂的对映选择性甲基化

  摘要：

  设计并合成了手性C 2对称的DMEU衍生物，作为锂的手性配体。在DMEU衍生物（11）和六甲基-二硅氮烷的存在下，1-四氢萘酮（1）的烯醇锂（2）与甲基碘在甲苯中的反应得到（S）-2-甲基-1-四氢萘酮（（S ）-3）达到92％ee。

  DOI：

  10.1016/s0040-4039(96)02372-6
• 作为产物：
  描述：

  ((1R, 2S)-2-azido-1-(benzyloxy)propyl)benzene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1S,2R)-2-Benzyloxy-1-methyl-2-phenyl-ethylamine
  参考文献：
  名称：

  A short enantioselective synthesis of ephedrine, amphetamine and their analogues via two stereocentered Co(III)-catalyzed hydrolytic kinetic resolution of racemic syn-benzyloxy epoxide

  摘要：

  An efficient route for the synthesis of 6 drugs belonging to phenethylamine and amphetamine classes in excellent overall yields and high optical purity has been described. The strategy involves introduction of stereogenic centers by means of two-stereocentered Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of racemic syn-benzyloxy epoxide followed by Pd-catalyzed regioselective cationic hydrogenation of amino alcohols as the key reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.010

文献信息

• Selective<i>O</i>-Benzylation of Aminoalkanols
  作者：X. Eric Hu、John M. Cassady

  DOI：10.1080/00397919508013428

  日期：1995.3

  A simple and one-step method has been developed for selective O-benzylation of aminoalkanols. Study of steric effects shows the best selectivity in adjacent 1 degrees-OH vs 2 degrees-CHNH2 and decreased selectivity in 2 degrees-OH vs 1 degrees-CH2NH2 and non adjacen aminoalkanol.
• A short enantioselective synthesis of ephedrine, amphetamine and their analogues via two stereocentered Co(III)-catalyzed hydrolytic kinetic resolution of racemic syn-benzyloxy epoxide
  作者：Komal G. Lalwani、Arumugam Sudalai

  DOI：10.1016/j.tetlet.2015.10.010

  日期：2015.11

  An efficient route for the synthesis of 6 drugs belonging to phenethylamine and amphetamine classes in excellent overall yields and high optical purity has been described. The strategy involves introduction of stereogenic centers by means of two-stereocentered Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of racemic syn-benzyloxy epoxide followed by Pd-catalyzed regioselective cationic hydrogenation of amino alcohols as the key reactions. (C) 2015 Elsevier Ltd. All rights reserved.
• Enantioselective methylation of the lithium enolate of 1-tetralone mediated by chiral C2-symmetric DMEU derivatives
  作者：Katsuyuki Ishii、Shin Aoki、Kenji Koga

  DOI：10.1016/s0040-4039(96)02372-6

  日期：1997.1

  Chiral C2-symmetric DMEU derivatives were designed and synthesized as chiral ligands for lithium. The reaction of the lithium enolate (2) of 1-tetralone (1) with methyl iodide in toluene in the presence of a DMEU derivative (11) and hexamethyl-disilazane gave (S)-2-methyl-1-tetralone ((S)-3) in up to 92% ee.

  设计并合成了手性C 2对称的DMEU衍生物，作为锂的手性配体。在DMEU衍生物（11）和六甲基-二硅氮烷的存在下，1-四氢萘酮（1）的烯醇锂（2）与甲基碘在甲苯中的反应得到（S）-2-甲基-1-四氢萘酮（（S ）-3）达到92％ee。