2-(benzylamino)benzenesulfonamide | 958-45-2

• 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: 2-(benzylamino)benzenesulfonamide
• CAS: 958-45-2
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: MVIFCLNZXFVYCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(benzylamino)benzenesulfonamide 在 dipotassium peroxodisulfate 作用下， 以 乙腈 为溶剂， 以80%的产率得到3-phenyl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide
  参考文献：
  名称：

  Sulfate Radical Anion (SO₄^•–) Mediated C(sp³)–H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles

  摘要：

  A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.

  DOI：

  10.1021/acs.joc.5b01872
• 作为产物：
  描述：

  3-phenyl-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide 在 硼烷-三甲胺络合物 作用下， 以 溶剂黄146 为溶剂， 生成 2-(benzylamino)benzenesulfonamide
  参考文献：
  名称：

  Biressi; Cantarelli; Carissimi, Farmaco, Edizione Scientifica, 1969, vol. 24, # 2, p. 199 - 220

  摘要：

  DOI：

文献信息

• Sulfate Radical Anion (SO₄^•–) Mediated C(sp³)–H Nitrogenation/Oxygenation in <i>N</i>-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles
  作者：Joydev K. Laha、K. S. Satyanarayana Tummalapalli、Akshay Nair、Nidhi Patel

  DOI：10.1021/acs.joc.5b01872

  日期：2015.11.20

  A transition-metal-free, K2S2O8-mediated intra-molecular, oxidative nitrogenation/oxygenation of C(sp(3))-H in N-aryl benzylic amines followed by oxidation at the benzylic center has been developed for the synthesis of benzamidine/benzoxazine heterocycles, providing an expedient access to quinazolin-4(3H)-ones, N-aryl-2-arylbenzimidazoles, and 4H-3,1-benzoxazin-4-ones. A considerable amount of work dealing with the mechanistic study to understand the crucial intramolecular cyclization step largely favors an iminium ion as the key intermediate.
• <i>N</i>-Benzylation/Benzylic CH Amidation Cascade by the (η³-Benzyl)palladium System in Aqueous Media: An Effective Pathway for the Direct Construction of 3-Phenyl-3,4-dihydro- (2<i>H</i>)-1,2,4-benzothiadiazine 1,1-Dioxides
  作者：Hidemasa Hikawa、Naoya Matsuda、Hideharu Suzuki、Yuusaku Yokoyama、Isao Azumaya

  DOI：10.1002/adsc.201300317

  日期：2013.8.12

  AbstractWe demonstrate a unique strategy for a benzylation/benzylic CH amidation cascade reaction by the (η3‐benzyl)palladium system derived from a palladium catalyst and benzyl alcohol. This tandem process is devised as a new synthetic route for 3‐phenyl‐3,4‐dihydro‐(2H)‐1,2,4‐benzothiadiazine‐1,1‐dioxide. Water plays an important role for the smooth generation of the (η3‐benzyl)palladium species, and a bis‐benzylated Pd(II) intermediate would be formed in our catalytic system. Atom economical processes such as benzylic CH activation, cascade reactions and chemoselective reactions in aqueous media have been developed.magnified image
• The Preparation of 4-Substituted Benzothiadiazines
  作者：E. Magnien、W. Tom、W. Oroshnik

  DOI：10.1021/jm00336a040

  日期：1964.11
• Biressi; Cantarelli; Carissimi, Farmaco, Edizione Scientifica, 1969, vol. 24, # 2, p. 199 - 220
  作者：Biressi、Cantarelli、Carissimi、Cattaneo、Ravenna

  DOI：——

  日期：——
• Access to 2‐Arylquinazolin‐4(3H)‐ones through Intramolecular Oxidative C(sp ³ )−H/N−H Cross‐Coupling Mediated by I ₂ /DMSO
  作者：Simiaomiao Wen、Yifan Du、Yiwen Liu、Xiaofeng Cui、Qixing Liu、Haifeng Zhou

  DOI：10.1002/ejoc.202101187

  日期：2022.1.27

  AbstractA novel approach for the synthesis of 2‐arylquinazolin‐4(3H)‐ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO‐mediated intramolecular oxidative cross‐coupling of 2‐(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram‐scale synthesis. A proposed reaction pathway based on some control experiments was also provided.