N-[1-(2-naphthyl)propyl]-P,P-diphenylphosphinic amide | 145425-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[1-(2-naphthyl)propyl]-P,P-diphenylphosphinic amide
• 英文别名: N-diphenylphosphoryl-1-naphthalen-2-ylpropan-1-amine
• CAS: 145425-09-8
• 化学式: C₂₅H₂₄NOP
• 分子量: 385.445
• InChiKey: IUGRYWWQBVAQRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  diethylzinc 、 (E)-N-(naphthalen-2-ylmethylene)-P,P-diphenylphosphinic amide 在 (1S,2R)-2-(morpholin-4-yl)-1-phenylpropanol 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 112.0h， 以84%的产率得到N-[1-(2-naphthyl)propyl]-P,P-diphenylphosphinic amide
  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

• Highly enantioselective alkylation of carbon–nitrogen double bonds. Catalytic and stoichiometric asymmetric synthesis of optically active amines by the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines
  作者：Kenso Soai、Toshihiro Hatanaka、Tohru Miyazawa

  DOI：10.1039/c39920001097

  日期：——

  The first highly enantioselective alkylation of carbon–nitrogen double bonds (of N-diphenylphosphinoylimines) with dialkylzinc reagents promoted by chiral amino alcohols afforded optically active phosphoramides (precursors of amines) in up to 91% enantiomeric excess.

  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）。
• 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.
• 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.