N-[1-(4-methoxyphenyl)propyl]-P,P-diphenylphosphinic amide | 892494-01-8

• 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: N-[1-(4-methoxyphenyl)propyl]-P,P-diphenylphosphinic amide
• 英文别名: N-[1-(4-methoxyphenyl)propyl]-P,P-diphenylphosphinoylamide；N-diphenylphosphoryl-1-(4-methoxyphenyl)propan-1-amine
• CAS: 892494-01-8
• 化学式: C₂₂H₂₄NO₂P
• 分子量: 365.412
• InChiKey: JMIRKPWKWOODRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[1-(4-methoxyphenyl)propyl]-P,P-diphenylphosphinic amide 在 oxonium 作用下， 生成 (1R)-1-(4-甲氧基苯基)-1-丙胺 、 (S)-1-(p-methoxyphenyl)propan-1-amine
  参考文献：
  名称：

  Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing N,N-dialkyl-1,2-diphenyl-2-aminoethanols as chiral ligands

  摘要：

  By fine-tuning the substituents on the nitrogen of (1S,2R) and (1R,2S)-1,2-diphenyl-2-aminoethanols, a chiral ligand 2b was obtained, which showed excellent enantioselectivity, with up to 94% e.e, for the asymmetric addition of diethylzinc to N-diphenylphosphinoylimines 1. In one example, the optically active amide 3c was converted into a new amine 5 with 98% e.e. by a reaction sequence involving Suzuki coupling and hydrolysis without racemization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01273-4
• 作为产物：
  描述：

  diethylzinc 、 N-(p-methoxybenzylidene)diphenylphosphinamide 在 (1R,2S)-N-2',4',6'-trimethylbenzyl-1,2-diphenyl-2-aminoethanol 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以89%的产率得到N-[1-(4-methoxyphenyl)propyl]-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  使用容易获得的N-单取代的氨基醇向亚胺中添加高度对映选择性的二乙基锌。

  摘要：

  通过精细筛选N，N-二取代和N-单取代的氨基醇，发现了一种容易获得的手性配体3c，它促进了二乙基锌添加到具有96-98％ee的亚胺中。平均而言，N-单取代的氨基醇比其N，N-二取代的类似物具有更高的对映选择性。这些结果表明，氨基醇的受限和刚性结构不是对二苯基膦基嘧啶的高对映选择性二烷基锌的绝对要求。[结构：见文字]

  DOI：

  10.1021/ol025728u

文献信息

• METHOD OF ENANTIOSELECTIVE ADDITION TO IMINES
  申请人：National Tsing Hua University

  公开号：US20150183811A1

  公开（公告）日：2015-07-02

  The present invention relates to a method of enantioselective addition to imines, including: reacting R 2 CH═NY with R 3 ZnR 4 in the presence of a compound represented by the following formula (I), in which Y, R 1 , R 2 , R 3 and R 4 are defined the same as the specification. Accordingly, the present invention can prepare secondary amines in high yields and enantiomeric excess by the above-mentioned method.

  本发明涉及一种对亚胺进行对映选择性加成的方法，包括：在以下化合物的存在下，将R2CH═NY与R3ZnR4反应，其中该化合物由以下式（I）表示，其中Y、R1、R2、R3和R4的定义与规范相同。因此，本发明可以通过上述方法高产率和对映过量地制备二级胺。
• Nickel-catalysed addition of dialkylzinc reagents to N-phosphinoyl- and N-sulfonylimines
  作者：Raquel Almansa、David Guijarro、Miguel Yus

  DOI：10.1016/j.tet.2006.11.056

  日期：2007.1

  A catalytic amount of a nickel complex (0.1-5.3 mol %) extraordinarily increases the reaction rate of the addition of dialkylzinc reagents to N-(diphenylphosphinoyl)- or N-(benzenesulfonyl)imines. The reaction of imines derived from both aromatic and aliphatic aldehydes with various dialkylzinc reagents in the presence of several nickel complexes gives the expected addition products in most cases in I h and in very good yields. In general, the formation of reduction by-products was not an important side reaction. The process represents a great improvement, with regard to the reaction rate and the yield of the addition products, in comparison with the reactions performed in the absence of the nickel catalyst, and reaction times are much shorter than the ones reported so far using other catalysts. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing cinchonidine and cinchonine as chiral ligands
  作者：Kenneth J.M Beresford

  DOI：10.1016/j.tetlet.2004.06.018

  日期：2004.7

  The use of the 'pseudoenantiomeric pair' of cinchonine and cinchonidine as ligands for the addition of diethylzinc to N-diphenylphosphinoylimines has been investigated. With 1 equiv of cinchonidine as ligand, a series of chiral amines was prepared in good yield and enantiomeric excesses of up to 94%. The use of 2.0 equiv of methanol as an achiral additive was found significantly to improve the selectivity of the addition when using 0.2 equiv of ligand, yielding ce's close to those obtained with a stoichiometric amount of ligand. (C) 2004 Elsevier Ltd. All rights reserved.
• US9193743B2
  申请人：——

  公开号：US9193743B2

  公开（公告）日：2015-11-24
• Highly Enantioselective Diethylzinc Addition to Imines Employing Readily Available <i>N</i>-Monosubstituted Amino Alcohols
  作者：Hai-Le Zhang、Xiao-Mei Zhang、Liu-Zhu Gong、Ai-Qiao Mi、Xin Cui、Yao-Zhong Jiang、Michael C. K. Choi、Albert S. C. Chan

  DOI：10.1021/ol025728u

  日期：2002.4.1

  easily accessible chiral ligand 3c, which promoted diethylzinc addition to imines with 96-98% ee, has been found by finely screening N,N-disubstituted and N-monosubstituted amino alcohols. N-monosubstituted amino alcohols, on average, gave slightly higher enantioselectivities than their N,N-disubstituted analogues. These results imply that the restricted and rigid structure of amino alcohol is not the absolute

  通过精细筛选N，N-二取代和N-单取代的氨基醇，发现了一种容易获得的手性配体3c，它促进了二乙基锌添加到具有96-98％ee的亚胺中。平均而言，N-单取代的氨基醇比其N，N-二取代的类似物具有更高的对映选择性。这些结果表明，氨基醇的受限和刚性结构不是对二苯基膦基嘧啶的高对映选择性二烷基锌的绝对要求。[结构：见文字]