(S)-N-(1,3-diphenylprop-2-ynyl)-P,P-diphenylphosphinic amide | 1187429-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (S)-N-(1,3-diphenylprop-2-ynyl)-P,P-diphenylphosphinic amide
• 英文别名: N-(1,3-diphenylprop-2-ynyl)-P,P-diphenylphosphinic amide；(S)-N-(1,3-diphenylprop-2-ynyl)-P,P-diphenylphosphinamide；(1S)-N-diphenylphosphoryl-1,3-diphenylprop-2-yn-1-amine
• CAS: 1187429-17-9
• 化学式: C₂₇H₂₂NOP
• 分子量: 407.452
• InChiKey: CVOMEJQVURKZHH-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(1,3-diphenylprop-2-ynyl)-P,P-diphenylphosphinic amide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以94.2%的产率得到(S)-N-(1,3-diphenylprop-2-ynyl)amine
  参考文献：
  名称：

  化学计量量的脯氨酸衍生的 β-氨基醇促进末端炔烃与 N-（二苯基膦酰基）亚胺的不对称加成

  摘要：

  描述了一种用于制备光学活性炔丙胺的新合成方法。通过使用二乙基锌和脯氨酸衍生的 β-氨基醇研究了芳香族、杂芳香族、脂肪族和 α,β-不饱和 N-（二苯基膦酰基）亚胺的炔基化反应。N-(二苯基膦酰基)-保护的炔丙胺可以以高产率合成，并且具有良好到优异的对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900342
• 作为产物：
  描述：

  N-亚苄基-P,P-二苯基次膦酸酰胺 、 苯乙炔 在 diethylzinc 、 (S)-(1-(naphthalen-2-ylmethyl)pyrrolidin-2-yl)methanol 作用下， 以 二氯甲烷 为溶剂， 反应 55.0h， 以78%的产率得到(S)-N-(1,3-diphenylprop-2-ynyl)-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  化学计量量的脯氨酸衍生的 β-氨基醇促进末端炔烃与 N-（二苯基膦酰基）亚胺的不对称加成

  摘要：

  描述了一种用于制备光学活性炔丙胺的新合成方法。通过使用二乙基锌和脯氨酸衍生的 β-氨基醇研究了芳香族、杂芳香族、脂肪族和 α,β-不饱和 N-（二苯基膦酰基）亚胺的炔基化反应。N-(二苯基膦酰基)-保护的炔丙胺可以以高产率合成，并且具有良好到优异的对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900342

文献信息

• Asymmetric Addition of Terminal Alkynes to<i>N</i>-(Diphenylphosphinoyl)imines Promoted by Stoichiometric Amounts of a Proline-Derived β-Amino Alcohol
  作者：Wenjin Yan、Bin Mao、Shaoqun Zhu、Xianxing Jiang、Zhongli Liu、Rui Wang

  DOI：10.1002/ejoc.200900342

  日期：2009.8

  preparation of optically active propargylamines is described. The alkynylation of aromatic, heteroaromatic, aliphatic and α,β-unsaturated N-(diphenylphosphinoyl)imines was investigated by using diethylzinc and a proline-derived β-amino alcohol. N-(Diphenylphosphinoyl)-protected propargylic amines can be synthesized in high yields and with good to excellent enantioselectivities. (© Wiley-VCH Verlag GmbH

  描述了一种用于制备光学活性炔丙胺的新合成方法。通过使用二乙基锌和脯氨酸衍生的 β-氨基醇研究了芳香族、杂芳香族、脂肪族和 α,β-不饱和 N-（二苯基膦酰基）亚胺的炔基化反应。N-(二苯基膦酰基)-保护的炔丙胺可以以高产率合成，并且具有良好到优异的对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Catalytic Asymmetric Addition of Alkyl and Aryl Alkynes to <i>N</i>-(Diphenylphosphinoyl)imines
  作者：Jun Ying、Xue-Dan Wu、Danny Wang、Lin Pu

  DOI：10.1021/acs.joc.6b01599

  日期：2016.10.7

  the asymmetric reaction of alkyl and aryl alkynes with N-(diphenylphosphinoyl)imines in the presence of Et2Zn and Ti(OiPr)4. It exhibits unprecedented high enantioselectivity (up to 85% ee) for a simple alkyl alkyne addition to the N-(diphenylphosphinoyl)imines. The easy removal of the N-(dipehenylphosphinoyl) protecting groups makes this method practically useful for the asymmetric synthesis of chiral

  甲3,3'-二（1- diphenylmethylpiperazinyl）甲基H 8 BINOL化合物，（小号） - 11，由（的曼尼希型反应制备小号）-H 8 BINOL与多聚甲醛和1-（二苯基甲基）哌嗪。该化合物可在Et 2 Zn和Ti（O i Pr）4存在下催化烷基和芳基炔烃与N-（二苯基膦酰基）亚胺的不对称反应。对于N-（二苯基膦酰基）亚胺的简单烷基炔烃加成，它表现出空前的高对映选择性（高达85％ee）。轻松去除N-（二苯甲酰基膦酰基）保护基使得该方法对于手性炔丙基胺的不对称合成实际上是有用的。
• 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.
• 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.