(S)-N-(1-phenyl-3-(thien-3-yl)prop-2-ynyl)-P,P-diphenylphosphinamide | 1252608-03-9

• 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: (S)-N-(1-phenyl-3-(thien-3-yl)prop-2-ynyl)-P,P-diphenylphosphinamide
• 英文别名: (1S)-N-diphenylphosphoryl-1-phenyl-3-thiophen-3-ylprop-2-yn-1-amine
• CAS: 1252608-03-9
• 化学式: C₂₅H₂₀NOPS
• 分子量: 413.48
• InChiKey: VMFTUJIUVAYRHT-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙炔基噻吩 、 N-亚苄基-P,P-二苯基次膦酸酰胺 在 Dimethylzinc 、 (S)-3,3'-二溴-1,1'-联-2-萘酚 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 反应 51.25h， 生成 (S)-N-(1-phenyl-3-(thien-3-yl)prop-2-ynyl)-P,P-diphenylphosphinamide 、 (R)-N-(1-phenyl-3-(thien-3-yl)prop-2-ynyl)-P,P-diphenylphosphinamide
  参考文献：
  名称：

  Enantioselective addition of terminal alkynes to N-(diphenylphosphinoyl)imines catalyzed by Zn–BINOL complexes

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.01.037

文献信息

• 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
  作者：Wenjin Yan、Peng Li、Jingchao Feng、Dong Wang、Shaoqun Zhu、Xianxing Jiang、Rui Wang

  DOI：10.1016/j.tetasy.2010.07.020

  日期：2010.8

  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.