(S)-N-(1-(naphthalen-2-yl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinamide | 1252608-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-N-(1-(naphthalen-2-yl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinamide
• 英文别名: (1S)-N-diphenylphosphoryl-1-naphthalen-2-yl-3-phenylprop-2-yn-1-amine
• CAS: 1252608-01-7
• 化学式: C₃₁H₂₄NOP
• 分子量: 457.511
• InChiKey: ZMIAOLWMDLSGFI-WJOKGBTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 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：

  N-(2-naphthylmethylene)diphenylphosphinamide 、 苯乙炔 在 (1-(thiophen-2-ylmethyl)pyrrolidin-2-yl)methanol 、 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 79.0h， 以77%的产率得到(S)-N-(1-(naphthalen-2-yl)-3-phenylprop-2-ynyl)-P,P-diphenylphosphinamide
  参考文献：
  名称：

  Design and synthesis of a tridentate ligand inspired by the phenomenon of self-assembly catalysis and its application in the asymmetric alkynylation of N-(diphenylphosphinoyl) imines

  摘要：

  On the basis of the phenomenon of self-assembly catalysis, a tridentate ligand was designed and synthesized in two steps. The application in alkynylation of N-(diphenylphosphinoyl) imines gave the expected products. Aromatic, heteroaromatic N-(diphenylphosphinoyl) imines were employed and gave optically active propargylic amines in good yields (up to 89%) and excellent enantioselectivities (up to 96%) by a simple experimental procedure. The direct use of sulfone amides in the alkynylation of N-(diphenylphosphinoyl) aliphatic imines made this method very attractive. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.020

文献信息

• Enantioselective addition of terminal alkynes to N-(diphenylphosphinoyl)imines catalyzed by Zn–BINOL complexes
  作者：Gonzalo Blay、Eric Ceballos、Alicia Monleón、José R. Pedro

  DOI：10.1016/j.tet.2012.01.037

  日期：2012.3

  Chiral nonracemic N-(diphenylphosphinoyl)-protected propargylic amines have been prepared by addition of terminal alkynes to N-(diphenylphosphinoyl)aldimines in the presence of dimethylzinc and 3,3'-dibromo-BINOL as catalyst. The reaction works with a variety of aromatic and heteroaromatic aldimines and with different alkynes, providing the expected products in generally good yields and enantiomeric excesses (up to 96%). (C) 2012 Elsevier Ltd. All rights reserved.