(R)-N-(1,3-diphenylprop-2-ynyl)acetamide | 957061-34-6

• 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: (R)-N-(1,3-diphenylprop-2-ynyl)acetamide
• 英文别名: N-((R)-1,3-diphenylprop-2-ynyl)acetamide；N-[(R)-1,3-diphenylprop-2-ynyl]acetamide；N-[(1R)-1,3-Diphenyl-2-propyn-1-yl]acetamide；N-[(1R)-1,3-diphenylprop-2-ynyl]acetamide
• CAS: 957061-34-6
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: JKFLCKBEHDWUPU-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  (R)-N-(1,3-diphenylprop-2-ynyl)acetamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (S)-N-(1,3-diphenylpropyl)acetamide
  参考文献：
  名称：

  Diastereoselective Alkynylation of N-p-Tolylsulfinylimines with Aluminum Acetylides

  摘要：

  The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.

  DOI：

  10.1021/jo071139w
• 作为产物：
  描述：

  N-benzylidene-1,1,1-trimethylsilanamine 以 二氯甲烷 、 氯仿 为溶剂， 反应 27.0h， 生成 (R)-N-(1,3-diphenylprop-2-ynyl)acetamide
  参考文献：
  名称：

  Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates

  摘要：

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.

  DOI：

  10.1021/ol0523087

文献信息

• Diastereoselective alkynylation of chiral phosphinoylimines: preparation of optically active propargylamines
  作者：Mounira Benamer、Serge Turcaud、Jacques Royer

  DOI：10.1016/j.tetlet.2009.11.091

  日期：2010.1

  Chiral phosphinoylimines were prepared from methylphenylphosphonamides and tested as new chiral and activated imines. The addition of aluminum acetylides was proved to be highly diastereoselective while lithium or magnesium acetylides gave poor results. The cleavage of the chiral auxiliary was done under mild conditions and allows the recovery of the starting phosphonamide without loss of optical purity

  由甲基苯基膦酰胺制备手性膦基嘧啶，并作为新的手性和活化亚胺进行测试。事实证明，添加乙炔铝具有很高的非对映选择性，而乙炔酸锂或镁的添加效果较差。手性助剂的裂解是在温和的条件下进行的，并且可以回收起始的膦酰胺而不会损失光学纯度。
• Diastereoselective alkynylation of glucose-modified imines with terminal alkynes
  作者：Jiangang Mao、Pengfei Zhang

  DOI：10.1016/j.tetasy.2009.02.056

  日期：2009.3

  The copper(I)-catalyzed enantioselective alkynylation of aldimines incorporating a 2,3,4,6-tetrakis-O-pivaloyl-D-glucopyranosyl (Piv(4)Glc) chiral auxiliary with terminal alkynes is reported. The present system provides a versatile tool for the construction of optically active propargylamine derivatives Good. yields and enantiomeric excess values were achieved with an array of imines and biologically active, propargylamine derivatives. (C) 2009 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of Propargylamides via 3,3‘-Disubstituted Binaphthol-Modified Alkynylboronates
  作者：T. Robert Wu、J. Michael Chong

  DOI：10.1021/ol0523087

  日期：2006.1.1

  Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.
• Diastereoselective Alkynylation of <i>N</i>-<i>p</i>-Tolylsulfinylimines with Aluminum Acetylides
  作者：Serge Turcaud、Farouk Berhal、Jacques Royer

  DOI：10.1021/jo071139w

  日期：2007.10.1

  The addition of alkynyl dimethyl aluminum compounds onto N-p-tolylsulfinylimines was investigated. The reaction was proved to be totally regioselective, leading to propargylamines with high diastereoselectivity (up to 99% de). Addition of aluminum derivatives gave a reversal of diastereoselectivity compared to the addition reaction of lithium acetylide.