N-(2-(1-hydroxybut-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide | 1394401-57-0

• 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: N-(2-(1-hydroxybut-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide
• 英文别名: N-[2-(1-hydroxybut-2-ynyl)phenyl]-4-methylbenzenesulfonamide
• CAS: 1394401-57-0
• 化学式: C₁₇H₁₇NO₃S
• 分子量: 315.393
• InChiKey: OWTLCFHVGQPSIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(1-hydroxybut-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide 在 silver(I) acetate 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以68%的产率得到(Z)-2-ethylidene-1-tosylindolin-3-ol
  参考文献：
  名称：

  Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols

  摘要：

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.

  DOI：

  10.1021/jo301198z
• 作为产物：
  描述：

  2-氨基苯甲醛 在 吡啶 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 5.17h， 生成 N-(2-(1-hydroxybut-2-yn-1-yl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (Z)-2-Methylene-1-sulfonylindolin-3-ols

  摘要：

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.

  DOI：

  10.1021/jo301198z

文献信息

• Transition-Metal-Free Decarboxylative Propargylic Substitution/Cyclization with either Azolium Enolates or Acyl Anions
  作者：Shenci Lu、Jun-Yang Ong、Si Bei Poh、Terence Tsang、Yu Zhao

  DOI：10.1002/anie.201801340

  日期：2018.5.14

  unprecedented transition‐metal‐free propargylic substitution reaction with either azolium enolates or acyl anions, which are generated from aldehydes under N‐heterocyclic carbene catalysis. This new catalytic activation operates on readily available cyclic propargylic carbamates through decarboxylation, and generates reactive allene intermediates that can undergo divergent cyclization pathways to deliver

  本文介绍了一种空前的无过渡金属的炔丙基取代反应，它与氮杂环卡宾催化下的醛类生成的烯醇氮或酰基阴离子。这种新的催化活化作用是通过脱羧作用在易于获得的环状丙炔基氨基甲酸酯上，并生成反应性丙二烯中间体，该中间体可以经历不同的环化途径，从而以高水平的效率和出色的对映选择性提供骨架多样的多环化合物。
• Rh(III)-Catalyzed C–H Activation of Benzamides and Chemodivergent Annulation with Benzoxazinanones: Substrate Controlled Selectivity
  作者：Danqing Ji、Xingwei Li

  DOI：10.1021/acs.orglett.3c02371

  日期：2023.10.6

  Decarboxylative annulation of propargyl carbamates with benzamides has been realized via rhodium-catalyzed C–H bond activation under mild conditions, delivering two distinct classes of heterocycles in high efficiency and selectivity under substrate control. This protocol provides a direct synthetic method for the preparation of functionalized 1,8-naphthyridines and isoindolinones.

  在温和条件下，通过铑催化的 C-H 键活化，实现了氨基甲酸炔丙酯与苯甲酰胺的脱羧环化，在底物控制下以高效率和选择性产生两类不同的杂环。该方案提供了制备功能化 1,8-萘啶和异吲哚酮的直接合成方法。
• Silver Acetate Catalyzed Hydroamination of 1-(2-(Sulfonylamino)phenyl)prop-2-yn-1-ols to (<i>Z</i>)<i>-</i>2-Methylene-1-sulfonylindolin-3-ols
  作者：Dewi Susanti、Fujiet Koh、Jeffrey Antonius Kusuma、Prasath Kothandaraman、Philip Wai Hong Chan

  DOI：10.1021/jo301198z

  日期：2012.9.7

  A method to prepare (Z)-2-methylene-1-sulfonylindolin-3-ols efficiently that relies on silver acetate catalyzed hydroamination of 1-(2-(sulfonylamino)phenyl)prop-2-yn-1-ols is reported. The reactions proceed rapidly at room temperature with catalyst loadings as low as 1 mol % under conditions that did not require the exclusion of air or moisture. The utility of this N-heterocyclic ring-forming strategy as a synthetic tool that makes use of unsaturated alcohols was exemplified by the conversion of the (Z)-2-methylene-1-sulfonylindolin-3-ol to examples of other members of the indole family of compounds.