N-(benzofuran-2-yl)-4-methyl-N-tosylbenzenesulfonamide

• 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-(benzofuran-2-yl)-4-methyl-N-tosylbenzenesulfonamide
• 英文别名: N,N-di(toluene-p-sulfonyl)(benzo[b]furan-2-yl)amine；N-(1-benzofuran-2-yl)-4-methyl-N-(4-methylphenyl)sulfonylbenzenesulfonamide
• 化学式: C₂₂H₁₉NO₅S₂
• 分子量: 441.529
• InChiKey: OQMMCIBRTYZXPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3-苯并呋喃 、 [(N-tosylimino)iodo]benzene 在 [Ru(II)(meso-tetrakis(tolyl)porphyrin)(CO)] 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以58%的产率得到N-(benzofuran-2-yl)-4-methyl-N-tosylbenzenesulfonamide
  参考文献：
  名称：

  Ruthenium(II) Porphyrin-Catalyzed Amidation of Aromatic Heterocycles

  摘要：

  Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles with iminoiodanes under mild conditions (CH2Cl2, 4 Angstrom molecular sieves, ultrasound, 40 degreesC) was achieved in moderate to good yields (up to 84%) and conversions (up to 99%). Only the N,N-ditosylamidated product was obtained for reactions involving heteroarenes, where X = O, S, or NTs. N-Alkyl- and N-aryl-substituted pyrroles, on the other hand, were shown to give the 3,4-diaminated adduct.

  DOI：

  10.1021/ol049232j

文献信息

• C–H Imidation and Dual C–H Bond Aminobromination of Five-Membered Heterocycles
  作者：Kai Sun、Yali Li、Ranran Feng、Shiqiang Mu、Xin Wang、Bing Zhang

  DOI：10.1021/acs.joc.9b02941

  日期：2020.1.17

  Here, we report a practical C-H imidation of five-membered heterocycles under metal-free conditions. We also report the first dual C-H bond aminobromination of thiophenes, with benzotriazole, saccharin, 1,2,4-triazole, benzimidazole, pyrazole, 4-bromopyrazole, 5-methyltetrazole, and dibenzenesulfonimides as effective amine sources. Mechanistic studies support the radical pathway of the imidation and aminobromination reactions.