3-(N-benzyl-4-methylphenylsulfonamido)prop-2-ynyl acetate | 1276027-43-0

• 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: 3-(N-benzyl-4-methylphenylsulfonamido)prop-2-ynyl acetate
• 英文别名: 3-[Benzyl-(4-methylphenyl)sulfonylamino]prop-2-ynyl acetate
• CAS: 1276027-43-0
• 化学式: C₁₉H₁₉NO₄S
• 分子量: 357.43
• InChiKey: YJPRVKWEBGJKBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(N-benzyl-4-methylphenylsulfonamido)prop-2-ynyl acetate 在 N-氯代丁二酰亚胺 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以71%的产率得到N-benzyl-2-chloro-N-tosylacrylamide
  参考文献：
  名称：

  Metal-Free Halonium Mediated Acetate Shifts of Ynamides To Access α-Halo Acrylamides/Acrylimides

  摘要：

  A metal-free acetate shift of 3-acetoxy ynamides to access alpha-iodo, bromo, and chloro acrylamides/acrylimides under very mild conditions is demonstrated. The Inherent alkyne activation of ynamides is sufficient to ensure the a-halo acrylamides/acrylimides in high yields without the addition of a catalyst. In all cases high Z-stereoselectivity is observed.

  DOI：

  10.1021/ol200269h
• 作为产物：
  描述：

  acetoxypropargyl bromide 、 N-benzyl-p-toluenesulfonamide 在 1,10-菲罗啉 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以98%的产率得到3-(N-benzyl-4-methylphenylsulfonamido)prop-2-ynyl acetate
  参考文献：
  名称：

  Zeo-Click合成：铜沸石催化的酰胺合成

  摘要：

  AbstractCopper(I)‐zeolites, especially copper(I)‐ultra stable Y zeolite (USY), are very efficient heterogeneous catalysts for the coupling of functionalized 1‐bromoalkynes and various nitrogen derivatives. Under these conditions, sulfonylated alkyl‐ or arylamines and various N‐heterocycles, such as oxazolidinones or indoles, could be efficiently transformed into the corresponding N‐alkynyl derivatives. However, imidazoles gave addition products rather than coupling products. The reaction conditions proved compatible with a variety of functional and protecting groups. Such zeolitic catalysts can be recycled and reused at least five times without significant deactivation. Low catalyst loading could be used (4 mol%) and as low as 0.8 mol% of this heterogeneous copper catalyst still gave good conversion and yields.magnified image

  DOI：

  10.1002/adsc.201400189