(R)-N-(1-phenylbutyl)-P,P-diphenylphosphinamide

• 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: (R)-N-(1-phenylbutyl)-P,P-diphenylphosphinamide
• 英文别名: (1R)-N-diphenylphosphoryl-1-phenylbutan-1-amine
• 化学式: C₂₂H₂₄NOP
• 分子量: 349.412
• InChiKey: WWTCKBQFBLBCHU-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯基次膦酰氯 在 [ReOCl3(OPPh3)(SMe2)] 、 (R,R)-bis[4-(4-t-Bu-Phe)-4,5-dihydrooxazol-2-yl]acetonitrile 、 二甲基苯基硅烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-N-(1-phenylbutyl)-P,P-diphenylphosphinamide
  参考文献：
  名称：

  Enantioselective Reduction of Imines Catalyzed by a Rhenium(V)−Oxo Complex

  摘要：

  An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)-oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium-oxo complex of the general formula (CNbox)Re(O)Cl2(OPPh3). Using this catalyst, a wide range of aromatic imines (including cyclic, acyclic, and heteroaromatic), alpha-iminoesters, and alpha,beta-unsaturated imines are reduced with good to excellent enantioselectivities.

  DOI：

  10.1021/ja050831a

文献信息

• Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction
  作者：Braja Gopal Das、Rajender Nallagonda、Dhananjay Dey、Prasanta Ghorai

  DOI：10.1002/chem.201501914

  日期：2015.9.1

  salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α‐amino esters, γ‐ and δ‐lactams, and isoindolinones have also been carried

  合成了空气/水分稳定，晶体和可储存的手性水杨基恶唑啉基氧化（V）配合物，并公开了其在氢化硅烷作为氢化物源的情况下催化不对称还原酮亚胺的催化应用。获得了广泛的底物范围，高收率和出色的对映选择性（最高99％）。此外，对映体纯α-氨基酯，γ-和δ-内酰胺以及异吲哚啉酮的合成也已使用该方法进行。最后，该方法已应用于具有药物相关性的合成靶标，例如R -（+）-沙丁胺碱和R -（+）-crispine A.
• Enantioselective MSPV Reduction of Ketimines Using 2-Propanol and (BINOL)Al^III
  作者：Christopher R. Graves、Karl A. Scheidt、SonBinh T. Nguyen

  DOI：10.1021/ol060110w

  日期：2006.3.1

  A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)Al-III/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.