(1R,2S)-1,2-Diphenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-ethanol | 23364-45-6

• 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: (1R,2S)-1,2-Diphenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-ethanol
• 英文别名: (1R,2S)-2-(benzylideneamino)-1,2-diphenylethanol
• CAS: 23364-45-6
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: GDBSIHIJCJTOMM-LEWJYISDSA-N

物化性质

• 沸点：
  442.3±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-1,2-Diphenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-ethanol 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.5h， 生成 (1R,2S)-2-benzylamino-1,2-diphenylethyl methyl ether
  参考文献：
  名称：

  手性路易斯碱性N-甲酰胺作为高效有机催化剂的发展，用于不对称还原酮和酮亚胺，具有空前的底物范围。

  摘要：

  已经开发出L-哌啉酸衍生的路易斯碱性N-甲酰胺，它是第一种高效的催化剂，用于以良好至高对映选择性不对称地还原芳族和脂族酮以及芳族和脂族酮亚胺。

  DOI：

  10.1039/b703307a
• 作为产物：
  描述：

  (1R,2S)-2-氨基-1,2-二苯基乙醇 、 苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 生成 (1R,2S)-1,2-Diphenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-ethanol
  参考文献：
  名称：

  手性路易斯碱性N-甲酰胺作为高效有机催化剂的发展，用于不对称还原酮和酮亚胺，具有空前的底物范围。

  摘要：

  已经开发出L-哌啉酸衍生的路易斯碱性N-甲酰胺，它是第一种高效的催化剂，用于以良好至高对映选择性不对称地还原芳族和脂族酮以及芳族和脂族酮亚胺。

  DOI：

  10.1039/b703307a

文献信息

• Easily accessible chiral amino-phosphinite ligands for highly enantioselective palladium-mediated allylic alkylation
  作者：Guoshu Chen、Xin Li、Haile Zhang、Liuzhu Gong、Aiqiao Mi、Xin Cui、Yaozhong Jiang、Michael C.K. Choi、Albert S.C. Chan

  DOI：10.1016/s0957-4166(02)00204-5

  日期：2002.5

  Palladium-catalyzed asymmetric allylic alkylation of 1,3-diplienyl-2-propenyl acetate with the dimethyl malonate-BSA-LiOAc system has been successfully carried out in the presence of easily prepared new chiral amino-phosphinite ligands such as 3b and 3c to result in good yields and excellent enantioselectivities of up to 95%, e.e. (C) 2002 Published by Elsevier Science Ltd.
• Diastereoselective Michael addition of 2H-2-oxo-1,4,2-oxaza phosphinanes to olefins
  作者：Jérôme Monbrun、Bénédicte Dayde、Henri-Jean Cristau、Jean-Noël Volle、David Virieux、Jean-Luc Pirat

  DOI：10.1016/j.tet.2010.10.078

  日期：2011.1

  Diastereoselective Michael additions of 2-hydrogeno-2-oxo-1,4,2-oxazaphosphinanes to olefins were described. Phosphinopeptide compounds were obtained in very good yield (up to 90%) and diasteromeric excesses ranging from 26 to 78%. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
• New Catalysts for the Asymmetric Hydrosilylation of Ketones Discovered by Mass Spectrometry Screening
  作者：Sulan Yao、Jun-Cai Meng、Gary Siuzdak、M. G. Finn

  DOI：10.1021/jo026365e

  日期：2003.4.1

  A method for determining enantiomeric excess by mass spectrometry was employed to screen a family of chiral phosphite P,N-ligands for activity in the rhodium-catalyzed asymmetric hydro-silylation of ketones. The identification of an effective set of ligands was followed by preliminary studies of the reaction scope and mechanism. Asymmetric induction of 84-88% ee for larger-scale reactions was observed, which is close to the level of the best alternative catalysts previously discovered. The screening method was shown to be applicable to a variety of substrates without the need for special optimization.
• Evolution of chiral Lewis basic N-formamide as highly effective organocatalyst for asymmetric reduction of both ketones and ketimines with an unprecedented substrate scope
  作者：Li Zhou、Zhouyu Wang、Siyu Wei、Jian Sun

  DOI：10.1039/b703307a

  日期：——

  L-Pipecolinic acid derived Lewis basic N-formamide has been developed as a first highly effective catalyst for the asymmetric reduction of aromatic and aliphatic ketones as well as aromatic and aliphatic ketimines in good to high enantioselectivity.

  已经开发出L-哌啉酸衍生的路易斯碱性N-甲酰胺，它是第一种高效的催化剂，用于以良好至高对映选择性不对称地还原芳族和脂族酮以及芳族和脂族酮亚胺。
• Enantiomer separation of 2‐halomandelic acids via diastereomeric salt formation with chiral <i>N</i>‐substituted 2‐amino‐2‐phenylethanols
  作者：Koichi Kodama、Yumi Kondo、Kosei Katayama、Moeka Yanagisawa、Takuji Hirose

  DOI：10.1002/chir.23630

  日期：2024.2

  Chiral N-substituted secondary 1,2-aminoalcohols have been developed for the enantioseparation of ortho-halomandelic acids (o-X-MAs) via diastereomeric salt formation. Two structural isomers, N-methyl-2-amino-1,2-diphenylethanol and N-benzyl-2-amino-2-phenylethanol, showed high separation abilities for o-X-MAs (X = Cl, Br, I). The chiral recognition mechanism was elucidated by crystallographic analysis

  手性N取代仲 1,2-氨基醇已开发用于通过非对映体盐形成原卤扁桃酸 ( o -X-MA) 的对映体分离。两种结构异构体N-甲基-2-氨基-1,2-二苯基乙醇和N-苄基-2-氨基-2-苯基乙醇对o -X-MA（X = Cl、Br、I）表现出较高的分离能力。通过难溶盐的晶体学分析阐明了手性识别机制。拆分剂氮原子上的取代基和结晶溶剂的包含稳定了盐并增强了它们的分离能力。