(E)-N-ethyl-4-methyl-N-(3-oxo-3-phenylprop-1-en-1-yl)benzenesulfonamide

• 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: (E)-N-ethyl-4-methyl-N-(3-oxo-3-phenylprop-1-en-1-yl)benzenesulfonamide
• 英文别名: beta-(N-p-Tosyl-ethylamino)-phenyl-vinyl-ketone；N-ethyl-4-methyl-N-[(E)-3-oxo-3-phenylprop-1-enyl]benzenesulfonamide
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: ZMPMARXOIGRHEJ-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-ethyl-4-methyl-N-(3-oxo-3-phenylprop-1-en-1-yl)benzenesulfonamide 以 乙醚 为溶剂， 反应 0.5h， 以7%的产率得到
  参考文献：
  名称：

  Photochemie von Aminoketonen. XV. Photochemische Acylgruppenwanderung in N-Tosyl-?-aminovinyl-phenyl-ketonen

  摘要：

  N-Tosyl-beta-aminovinyl-phenyl-ketones 1a - i are prepared in good yields from beta-chlorovinyl-phenyl-ketones by reaction with the sodium salts of tosyl amides in dry DMF at room temperature. In contrast to the relatively photostable N,N-dialkyl-beta-aminovinyl-aryl-ketones the electronically excited 1 give irreversible chemical reactions within a few minutes. Among other not identified photoproducts the alpha-tosyl-beta-aminovinyl-phenyl-ketones 2 were found. From the experimental results it is evident that the migration of the tosyl group prefers a radical-type two step reaction through an intermediate X/Y of a (1,5)-N --> O-tosylrearrangement.

  DOI：

  10.1002/prac.19933350107
• 作为产物：
  描述：

  N-乙基对甲苯磺酰胺 、 1-benzoyl-2-chloroethene 在 sodium hydride 作用下， 生成 (E)-N-ethyl-4-methyl-N-(3-oxo-3-phenylprop-1-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Photochemie von Aminoketonen. XV. Photochemische Acylgruppenwanderung in N-Tosyl-?-aminovinyl-phenyl-ketonen

  摘要：

  N-Tosyl-beta-aminovinyl-phenyl-ketones 1a - i are prepared in good yields from beta-chlorovinyl-phenyl-ketones by reaction with the sodium salts of tosyl amides in dry DMF at room temperature. In contrast to the relatively photostable N,N-dialkyl-beta-aminovinyl-aryl-ketones the electronically excited 1 give irreversible chemical reactions within a few minutes. Among other not identified photoproducts the alpha-tosyl-beta-aminovinyl-phenyl-ketones 2 were found. From the experimental results it is evident that the migration of the tosyl group prefers a radical-type two step reaction through an intermediate X/Y of a (1,5)-N --> O-tosylrearrangement.

  DOI：

  10.1002/prac.19933350107

文献信息

• Copper(<scp>i</scp>)-catalyzed N–H olefination of sulfonamides for <i>N</i>-sulfonyl enaminone synthesis
  作者：Xiao Liang、Xin Huang、Mingteng Xiong、Kexin Shen、Yuanjiang Pan

  DOI：10.1039/c8cc04385j

  日期：——

  copper-catalyzed N–H olefination of sulfonamides for enaminone synthesis using saturated ketones as olefin sources. With TEMPO derivatives and O2 as oxidants, this method provided an efficient way to produce various enaminones in good yields. Mechanistic studies helped figure out the stable intermediates and develop novel methodologies for the difunctionalization of saturated ketones.

  该通讯报道了使用饱和酮作为烯烃源的铜催化磺酰胺的NH烯化反应，用于烯胺合成。以TEMPO衍生物和O 2为氧化剂，该方法提供了一种以高收率生产各种烯胺酮的有效方法。机理研究有助于找出稳定的中间体，并为饱和酮的双官能化开发了新的方法。