N-(methanesulfonyl)-3-amino-1,3-diphenylprop-1-yne | 832732-23-7

• 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: N-(methanesulfonyl)-3-amino-1,3-diphenylprop-1-yne
• 英文别名: Methanesulfonamide, N-(1,3-diphenyl-2-propynyl)-；N-(1,3-diphenylprop-2-ynyl)methanesulfonamide
• CAS: 832732-23-7
• 化学式: C₁₆H₁₅NO₂S
• 分子量: 285.367
• InChiKey: GRKSFQHPFYEEJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(苯基亚甲基)甲磺酰胺 、 苯乙炔 在 Dimethylzinc 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以78%的产率得到N-(methanesulfonyl)-3-amino-1,3-diphenylprop-1-yne
  参考文献：
  名称：

  Dimethylzinc-Mediated Alkynylation of Imines

  摘要：

  [GRAPHICS]The treatment of various aromatic and aliphatic aldimines with a mixture of a terminal alkyne and a commercially available dimethylzinc solution in toluene yields the corresponding protected propargylic amines in moderate to excellent yields. The reaction proceeds in the absence of any activator. These observations led to the development of a three-component synthesis of propargylic amines in which the product was obtained upon mixing an aldehyde with ortho-methoxyaniline and phenylacetylene in the presence of dimethylzinc, through in situ formation of the corresponding imine.

  DOI：

  10.1021/jo052273o

文献信息

• Heteropoly Acid-catalyzed Direct Substitution of 2-Propynyl Alcohols with Sulfonamides
  作者：J. S. Yadav、B. V. Subba Reddy、T. Srinivasa Rao、B. Bala. M. Krishna、G. G. K. S. Narayana Kumar

  DOI：10.1246/cl.2007.1472

  日期：2007.12.5

  Direct substitution of the hydroxy group in 2-propynyl alcohols with sulfonamides has been achieved using 5 mol % of phosphomolybdic acid supported on silica gel (PMA/SiO2) under mild reaction cond...

  在温和的反应条件下，使用 5 mol% 的磷钼酸负载在硅胶 (PMA/SiO2) 上，用磺酰胺直接取代了 2-丙炔醇中的羟基。
• Alkynylation of N-tosylimines with aryl acetylenes promoted by ZnBr2 and N,N-diisopropylethylamine in acetonitrile
  作者：Ka Young Lee、Chang Gon Lee、Jeong Eun Na、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2004.11.046

  日期：2005.1

  We found a suitable condition for the effective alkynylation of N-tosylimines with aryl acetylenes. The reaction tosylimines and aryl acetylenes in the presence of ZnBr2, and DIEA (N,N -diisopropylethylamine) in CH3CN afforded the desired N-tosyl propargylamines in moderate to good yields. (C) 2004 Elsevier Ltd. All rights reserved.
• Dimethylzinc-Mediated Alkynylation of Imines
  作者：Lorenzo Zani、Silvia Alesi、Pier Giorgio Cozzi、Carsten Bolm

  DOI：10.1021/jo052273o

  日期：2006.2.1

  [GRAPHICS]The treatment of various aromatic and aliphatic aldimines with a mixture of a terminal alkyne and a commercially available dimethylzinc solution in toluene yields the corresponding protected propargylic amines in moderate to excellent yields. The reaction proceeds in the absence of any activator. These observations led to the development of a three-component synthesis of propargylic amines in which the product was obtained upon mixing an aldehyde with ortho-methoxyaniline and phenylacetylene in the presence of dimethylzinc, through in situ formation of the corresponding imine.