N-[1-(4-methylphenyl)propyl]-P,P-diphenylphosphinoylamide | 145425-10-1

• 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-methylphenyl)propyl]-P,P-diphenylphosphinoylamide
• 英文别名: N-diphenylphosphoryl-1-(4-methylphenyl)propan-1-amine
• CAS: 145425-10-1
• 化学式: C₂₂H₂₄NOP
• 分子量: 349.412
• InChiKey: DDPJLTWMDNAGRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[1-(4-methylphenyl)propyl]-P,P-diphenylphosphinoylamide 在 oxonium 作用下， 生成 (R)-1-对甲苯丙烷-1-胺 、 (1S)-(4'-methylphenyl)propylamine
  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-(4-methybenzylidene)-P,P-diphenylphosphinamide 在 (1S,2R)-2-(morpholin-4-yl)-1-phenylpropanol 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 90.0h， 以75%的产率得到N-[1-(4-methylphenyl)propyl]-P,P-diphenylphosphinoylamide
  参考文献：
  名称：

  碳氮双键的高度对映选择性烷基化。通过将二烷基锌试剂对映选择性加成到N-二苯基膦基嘧啶上来催化和化学计量不对称地合成光学活性胺

  摘要：

  用手性氨基醇促进的二烷基锌试剂对（N-二苯基膦基嘧啶的）碳-氮双键进行的第一个高对映选择性烷基化可提供高达91％的对映体过量的光学活性磷酰胺（胺的前体）。

  DOI：

  10.1039/c39920001097

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。
• 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]
• Chiral amino alcohols bound to diimines, diamines and dendrimers as chiral ligands for the enantioselective ethylation of N-diphenylphosphinylimines
  作者：Takefumi Suzuki、Yutaka Hirokawa、Koji Ohtake、Takanori Shibata、Kenso Soai

  DOI：10.1016/s0957-4166(97)00553-3

  日期：1997.12

  Chiral diimines, diamines and dendrimers possessing 2, 4 and 8 ephedrine derivatives are utilized as chiral ligands for the enantioselective addition of diethylzinc to N-diphenylphosphinylimines to afford enantiomerically enriched N-diphenylphosphinylamines in up to 93% e.e. (C) 1997 Elsevier Science 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