Naphthalene-2-sulfonic acid (2-bromo-phenyl)-amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthalene-2-sulfonic acid (2-bromo-phenyl)-amide
• 英文别名: N-(2-bromophenyl)naphthalene-2-sulfonamide
• 化学式: C₁₆H₁₂BrNO₂S
• 分子量: 362.247
• InChiKey: KARWSJXFAOMWLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Naphthalene-2-sulfonic acid (2-bromo-phenyl)-amide 、 alkaline earth salt of/the/ methylsulfuric acid 生成 N-(2-bromophenyl)-N-methylnaphthalene-2-sulfonamide
  参考文献：
  名称：

  Synthetic use of 1,1,2,2-tetraphenyldisilane for the preparation of biaryls through the intramolecular free radical ipso-substitution of N-(2-bromoaryl)arenesulfonamides

  摘要：

  Treatment of various N-methyl-N-(2-bromoaryl)arenesulfonamides (1a-g, 1i, and 1m) with 1,1,2,2-tetraphenyldisilane and AIBN under heating conditions gave the corresponding biaryl products (2a-g, 2i, and 2m) in moderate yields through the intramolecular radical ipso-substitution. However, N-H foe N-(2-brornoaryl)arenesulfonamides Ih and 2-bromoaryl arenesulfonate 1j did not give the corresponding biarys. 1,1,2,2-Tetraphenyldisilane is the most effective reagent for 1,5-ipso-substitution on the sulfonamides among typical radical reagents such as diphenylsilane, tributyltin hydride, tris(trimethylsilyl)silane, and 1,1,2,2-tetraphenyldisilane. Furthermore, 1,1,2,2 tetraphenyldisilane has the advantages of low toxicity, stability, and ease of preparation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00560-9
• 作为产物：
  描述：

  2-bromo-N,N-di(naphth-2ylsulphonyl)aniline 、 dichlorobis(triphenylphosphine)palladium[II] 以8%的产率得到
  参考文献：
  名称：

  AMES, D. E.;OPALKO, A., TETRAHEDRON, 1984, 40, N 10, 1919-1925

  摘要：

  DOI：