N-ethynyl-4-methyl-N-(3-methylbut-2-en-1-yl)benzenesulfonamide | 1437788-40-3

• 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: N-ethynyl-4-methyl-N-(3-methylbut-2-en-1-yl)benzenesulfonamide
• CAS: 1437788-40-3
• 化学式: C₁₄H₁₇NO₂S
• 分子量: 263.36
• InChiKey: JEPWBKCEHHGVKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-ethynyl-4-methyl-N-(3-methylbut-2-en-1-yl)benzenesulfonamide 在 di(rhodium)tetracarbonyl dichloride 、 3,5-二氯吡啶 N-氧化物 、 三(1,1,1,3,3,3-六氟-2-丙基)亚磷酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以87%的产率得到
  参考文献：
  名称：

  Generation of Rhodium(I) Carbenes from Ynamides and Their Reactions with Alkynes and Alkenes

  摘要：

  Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]-hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.

  DOI：

  10.1021/ja4047069
• 作为产物：
  描述：

  4-methyl-N-(3-methylbut-2-enyl)benzenesulfonamide 在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 33.0h， 生成 N-ethynyl-4-methyl-N-(3-methylbut-2-en-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Generation of Rhodium(I) Carbenes from Ynamides and Their Reactions with Alkynes and Alkenes

  摘要：

  Rh(I) carbenes were conveniently generated from readily available ynamides. These metal carbene intermediates could undergo metathesis with electron-rich or neutral alkynes to afford 2-oxopyrrolidines or be trapped by tethered alkenes to yield 3-azabicyclo[3.1.0]-hexanes, a common skeleton in numerous bioactive pharmaceuticals. Although the scope of the former is limited, the latter reaction tolerates various substituted alkenes.

  DOI：

  10.1021/ja4047069

文献信息

• 1,4-Conjugate addition/esterification of <i>ortho</i>-quinone methides in a multicomponent reaction
  作者：Renjie Chen、Yu Liu、Sunliang Cui

  DOI：10.1039/c8cc07328g

  日期：——

  A novel 1,4-conjugate addition/esterification of ortho-quinone methides in a multicomponent reaction has been developed. In this protocol, numerous carboxylic acids, ynamides and in situ generated ortho-quinone methides could assemble rapidly to constitute this process for the synthesis of functionalized 3,3-diarylpropanamides with sufficient structural diversity. Furthermore, the products could be

  的新的1,4-共轭加成/酯化邻-quinone的甲基化物中的多组分反应已经研制成功。在该方案中，许多羧酸，乙酰胺和原位生成的邻醌甲基化物可以迅速组装，从而构成用于合成具有足够结构多样性的官能化3,3-二芳基丙酰胺的过程。此外，可以将产物转化为一系列化合物。
• Oxoarylation of ynamides with N-aryl hydroxamic acids
  作者：Changwei Chen、Hongyu Zhang、Gang Xu、Sunliang Cui

  DOI：10.1016/j.cclet.2021.02.054

  日期：2021.8

  building blocks in organic synthesis. Therefore, the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting. Herein, we report an oxoarylation of ynamides with N-aryl hydroxamic acids. In the presence of catalytic Cu(OTf)2, both the terminal and internal ynamides could undergo an addition/[3,3] sigmatropic rearrangement cascade with N-aryl hydroxamic

  炔烃是富含电子的炔烃，具有独特的反应性，可作为有机合成中的灵活构件。因此，以优异的选择性和效率转化ynamides的研究是有吸引力和有趣的。在此，我们报告了 ynamides 与N-芳基异羟肟酸的氧代芳基化。在催化 Cu (OTf) 2存在下，末端和内部炔酰胺都可以与N-芳基异羟肟酸发生加成 / [3,3] σ 重排级联反应以实现氧代芳基化，同时提供选择性进入（邻氨基) 芳基乙酰胺和羟吲哚。此外，进行了氘标记反应和克级反应以探索机制并展示可扩展性。