N-benzyl-N-(3-bromobenzo[b]thiophen-2-yl)-4-methylbenzenesulfonamide | 1453196-31-0

• 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-benzyl-N-(3-bromobenzo[b]thiophen-2-yl)-4-methylbenzenesulfonamide
• 英文别名: N-benzyl-N-(3-bromobenzo[b]thiophen-2-yl)-4-methyl-benzenesulfonamide
• CAS: 1453196-31-0
• 化学式: C₂₂H₁₈BrNO₂S₂
• 分子量: 472.426
• InChiKey: KBAFAMATQMINLG-UHFFFAOYSA-N

物化性质

• 沸点：
  609.1±65.0 °C(predicted)
• 密度：
  1.505±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-benzyl-4-methyl-N-{2-[2-(methylthio)phenyl]ethynyl}benzenesulfonamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到N-benzyl-N-(3-bromobenzo[b]thiophen-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Electrophilic Cyclization of o-Anisole- and o-Thioanisole-Substituted Ynamides­: Synthesis of 2-Amidobenzofurans and 2-Amidobenzothiophenes

  摘要：

  A facile synthesis of 3-substituted 2-amidobenzofurans and 2-amidobenzothiophenes via electrophilic cyclization reaction of o-anisole- and o-thioanisole-substituted ynamides with I-2, NBS and NCS was developed. The products 3-iodo-2-amidobenzofurans were further transferred into 3-aryl-, 3-alkynyl, and 3-vinyl-2-amidobenzofurans via Pd-catalyzed reactions such as Suzuki-Miyaura and Sonogashira cross-coupling reactions and the Heck reaction.

  DOI：

  10.1055/s-0033-1338481

文献信息

• Step‐Economical Route to 2‐Amido‐3‐bromobenzo[ <i>b</i> ]thiophenes <i>via</i> Ynamide Formation and Selectfluor‐Mediated Oxidative Bromocyclization
  作者：Su Jeong Hong、Chang Ju Yoon、Hee Nam Lim、Hyun‐Suk Yeom

  DOI：10.1002/ejoc.202101093

  日期：2021.11.8

  AbstractA one‐pot synthesis of 2‐amido‐3‐bromobenzo[b]thiophenes based on C−N coupling and oxidative bromocyclization reactions was developed. This enables a modular approach to obtain diverse substituents at the C2 position of benzothiophenes by employing structurally modified sulfonamides. Oxidative cyclization was driven by Selectfluor and represents a previously unreported recycling method for the bromide anion byproducts of the C−N bond coupling step. The details of the study are described fully herein.