(+/-)-erythro-α'-benzylidenamino-bibenzyl-α-ol; N-benzylidene-dl-diphenylhydroxyethylamine | 162237-42-5

• 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: (+/-)-erythro-α'-benzylidenamino-bibenzyl-α-ol; N-benzylidene-dl-diphenylhydroxyethylamine
• 英文别名: N-Benzyliden-(+)-diphenyloxaethylamin；(+/-)-erythro-α'-Benzylidenamino-bibenzyl-α-ol; N-Benzyliden-dl-diphenyloxaethylamin；(1S,2R)-2-(benzylideneamino)-1,2-diphenylethanol
• CAS: 162237-42-5
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: GDBSIHIJCJTOMM-RTWAWAEBSA-N

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：

  (+/-)-erythro-α'-benzylidenamino-bibenzyl-α-ol; N-benzylidene-dl-diphenylhydroxyethylamine 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (2R,3S,5S,6R)-(+/-)-3-phenyl-3-(2-oxo-3,5,6-triphenyl-2λ5-[1,4,2]oxazaphosphinan-2-yl)-methyl propionate
  参考文献：
  名称：

  Diastereoselective Michael addition of 2H-2-oxo-1,4,2-oxaza phosphinanes to olefins

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.10.078
• 作为产物：
  描述：

  (1S,2R)-2-氨基-1,2-二苯基乙醇 、 苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 (+/-)-erythro-α'-benzylidenamino-bibenzyl-α-ol; N-benzylidene-dl-diphenylhydroxyethylamine
  参考文献：
  名称：

  通过2-吡啶基硫酯的烯醇钛与带有手性助剂的亚胺的缩合立体选择性合成β-内酰胺

  摘要：

  通过2-吡啶基硫酯的烯醇钛与手性亚胺的缩合，β-内酰胺的立体选择性合成中已测试了几种胺作为手性助剂。胺选自以下化合物：苄基胺，β-氨基醇，β-杂取代的α-氨基酯。廉价且可以两种对映体形式获得的α-甲基苄胺被鉴定为手性助剂，通常结合了良好的反应性和令人满意的立体控制水平。为了说明该方法的潜力，制备了肾素抑制剂成分的前体。介绍了立体化学结果的初步合理化。

  DOI：

  10.1016/s0040-4020(01)85521-6

文献信息

• Stereoselective Synthesis of γ-Lactams from Imines and Cyanosuccinic Anhydrides
  作者：Darlene Q. Tan、Ashkaan Younai、Ommidala Pattawong、James C. Fettinger、Paul Ha-Yeon Cheong、Jared T. Shaw

  DOI：10.1021/ol402554n

  日期：2013.10.4

  A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization

  亚胺和酸酐之间的反应已经开发出手性二取代酸酐和手性亚胺。具有三个立体中心（包括一个四元中心）的高度取代的 γ-内酰胺的合成在室温下以高产率进行，并且在大多数情况下具有高非对映选择性。对映体纯的烷基取代酸酐不进行差向异构化，从而提供对映体纯的五取代内酰胺产品的途径。
• Synthesis, reactivity and stereochemistry of new phosphorus heterocycles with 5- or 6-membered rings
  作者：Henri-Jean Cristau、Jean-Luc Pirat、David Virieux、Jérôme Monbrun、Ciptadi Ciptadi、Yves-Alain Bekro

  DOI：10.1016/j.jorganchem.2004.11.035

  日期：2005.5

  Syntheses of novel phosphorus heterocycles containing α-amino or α-hydroxyphosphonic or phosphinic acids motifs are developed. 2,3-dihydro-1,3-oxaphospholes (1) and 1,4,2-oxazaphosphinanes (2) exhibit a reactive part, respectively the enolether moiety and the P–H bond, which allows various structural modifications: (i) for 1a, by introduction of amino substituents, (ii) for 2a, by hydroxy- or aminoalkylation

  开发了包含α-氨基或α-羟基膦酸或次膦酸基序的新型磷杂环的合成。2,3-二氢-1,3-氧杂磷腈（1）和1,4,2-氧杂氮杂膦（2）具有反应性，分别是烯醇醚部分和PH键，可进行各种结构修饰：对于1a，通过引入氨基取代基，（ii）对于2a，通过羟基或氨基烷基化，通过迈克尔加成或通过P-芳基化。这些反应通常表现出良好的或什至优异的动力学非对映选择性，这通常可以通过过渡态的分子模型来预测。
• 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.
• (β-Amino alcohol)(arene)ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Functionalized Ketones − Scope, Isolation of the Catalytic Intermediates, and Deactivation Processes
  作者：Kathelyne Everaere、André Mortreux、Michel Bulliard、Johannes Brussee、Arne van der Gen、Guy Nowogrocki、Jean-François Carpentier

  DOI：10.1002/1099-0690(200101)2001:2<275::aid-ejoc275>3.3.co;2-e

  日期：2001.1
• Erlenmeyer, Justus Liebigs Annalen der Chemie, 1899, vol. 307, p. 99
  作者：Erlenmeyer

  DOI：——

  日期：——