6-methyl-6,7-dihydro-5-thia-6-aza-dibenzo[a,c]cycloheptene-5,5-dioxide | 42060-54-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 6-methyl-6,7-dihydro-5-thia-6-aza-dibenzo[a,c]cycloheptene-5,5-dioxide
• 英文别名: 6-methyl-6,7-dihydrodibenzo[d,f][1,2]thiazepine 5,5-dioxide；6,7-dihydro-6-methyl-dibenzo[d,f][1,2]thiazepine 5,5-dioxide；6-methyl-7H-benzo[d][1,2]benzothiazepine 5,5-dioxide
• CAS: 42060-54-8
• 化学式: C₁₄H₁₃NO₂S
• 分子量: 259.329
• InChiKey: FTKNKFNBVBTCOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  o-Amino-N-benzolsulfonyl-N-methylbenzylamin 生成 6-methyl-6,7-dihydro-5-thia-6-aza-dibenzo[a,c]cycloheptene-5,5-dioxide
  参考文献：
  名称：

  Huppatz,J.L., Australian Journal of Chemistry, 1973, vol. 26, p. 1307 - 1318

  摘要：

  DOI：

文献信息

• Palladium-catalysed direct heteroarylation of bromobenzenes bearing SO2R substituents at C2 or C4
  作者：Charles Beromeo Bheeter、Rongwei Jin、Jitendra K. Bera、Henri Doucet

  DOI：10.1039/c3ra40769a

  日期：——

  Palladium-catalysed direct arylation of 4- or 2-bromobenzenesulfonic acid derivatives in the presence of a variety of heteroaromatics was found to proceed using 0.1–0.5 mol% palladium acetate as the catalyst. However, both the nature and position of the SO2R substituent on such bromobenzenes has an influence on the reaction rates and yields. The presence of SO2Et or SO2NEt2 at the C2 or C4 position of bromobenzene is tolerated. Good results were also obtained from bromobenzene substituted at C4 by SO2NHPh or SO2OPh. On the other hand, the reactions of bromobenzenes bearing either SO2N(Me)CH2Ph or SO2OAr at C2 led in some cases to intramolecular reactions instead of the desired intermolecular couplings. Some reactions were performed in cyclopentyl methyl ether, which can be considered as a green solvent.

  使用0.1-0.5%摩尔的醋酸钯作为催化剂，在多种杂芳环存在下，发现钯催化的4-或2-溴苯磺酸衍生物的直接芳基化反应可以进行。然而，溴苯上SO2R取代基的性质和位置对反应速率和产率有影响。在溴苯的C2或C4位置存在SO2Et或SO2NEt2是可以容忍的。在C4位置由SO2NHPh或SO2OPh取代的溴苯也得到了良好的结果。另一方面，在C2位置带有SO2N(Me)CH2Ph或SO2OAr的溴苯的反应在某些情况下会导致分子内反应，而不是所期望的分子间偶联。一些反应在环戊基甲基醚中进行，这种溶剂可以被认为是一种环保溶剂。
• Structurally Diverse Synthesis of Five-, Six-, and Seven-Membered Benzosultams through Electrochemical Cyclization
  作者：Aiyun Liu、Tiantian Guo、Shuangshuang Zhang、Han Yang、Qi Zhang、Yonghai Chai、Shengyong Zhang

  DOI：10.1021/acs.orglett.1c02128

  日期：2021.8.20

  to structurally diverse synthesis of benzosultams from aryl sulfonamides through an electrochemical cyclization. Upon variation of the ortho substituent on aryl sulfonamides, five-, six-, and seven-membered benzosultams were efficiently assembled in an atom- and resource-economic manner. The generality of the process is demonstrated by the formation of five- to seven-membered cyclic products from 42

  我们开发了一种无金属和无氧化剂的方法，通过电化学环化从芳基磺酰胺合成结构多样的苯并磺胺。根据芳基磺酰胺上的邻位取代基的变化，五元、六元和七元苯并磺胺以原子和资源经济的方式有效组装。该过程的通用性通过从 42 种带有不同电子效应和空间位阻的取代基的底物形成 5 到 7 元环状产物来证明。
• Palladium-Catalyzed Regio- and Chemo­selective Reactions of 2-Bromobenzyl Bromides: Expanding the Scope for the Synthesis of Biaryls Fused to a Seven-Membered Sultam
  作者：Joydev K. Laha、Shubhra Sharma、Neetu Dayal

  DOI：10.1002/ejoc.201501032

  日期：2015.12

  Speedy access to biaryls fused to seven-membered sultams was achieved by starting from readily accessible N-alkylbenzenesulfonamides and 2-bromobenzyl bromides. The protocol features a domino reaction and proceeds through an N-benzylation followed by an intramolecular direct C–H arylation that occurs ortho to the sulfonamide group.

  通过从容易获得的 N-烷基苯磺酰胺和 2-溴苄基溴开始，快速获得与七元磺胺稠合的联芳基化合物。该方案的特点是多米诺反应，并通过 N-苄基化进行，然后是在磺酰胺基团邻位发生的分子内直接 C-H 芳基化。
• Palladium-Catalysed Intramolecular Direct Arylation of 2-Bromobenzenesulfonic Acid Derivatives
  作者：Charles Beromeo Bheeter、Jitendra K. Bera、Henri Doucet

  DOI：10.1002/adsc.201200793

  日期：2012.12.14

  arylation of 2-bromobenzenesulfonic acid derivatives was found to proceed using 1 mol% of palladium acetate as the catalyst. The influence of the substituents on the phenol moiety of 2-bromobenzenesulfonic acid phenyl esters reveals that electron-donating substituents favour the reaction while electron-withdrawing ones are unfavourable. The reactivity of sulfonamides was also studied and, in all cases

  发现使用1mol％乙酸钯作为催化剂进行2-溴苯磺酸衍生物的钯催化的分子内直接芳基化。取代基对2-溴苯磺酸苯基酯的酚部分的影响表明，供电子取代基有利于反应，而吸电子取代基不利。还研究了磺酰胺的反应性，并且在所有情况下，均观察到sp 2 CH与sp 3 CH的选择性活化。在氮上同时带有苯基和苄基取代基的磺酰胺选择性地产生六元环产物。
• α-Haloarylsulfonamides: multiple cyclization pathways to skeletally diverse benzofused sultams
  作者：Dinesh Kumar Rayabarapu、Aihua Zhou、Kyu Ok Jeon、Thiwanka Samarakoon、Alan Rolfe、Hina Siddiqui、Paul R. Hanson

  DOI：10.1016/j.tet.2008.11.053

  日期：2009.4

  The development of new methods to skeletally diverse sultams based oil a central alpha-halo benzene sulfonamide building block is reported. Several salient features of this building block are Utilized ill multiple reaction pathways, including the Fleck reaction, C- and O-arylation, Sonogashira-Pauson-Khand, Sonogashira-intramolecular hydroamination, and domino aza-Michael-Heck for the generation of five-, six-, and seven-membered benzofused bicyclic and tricyclic sultams. (C) 2008 Elsevier Ltd. All rights reserved.