2-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide
• 英文别名: 2-methyl-6H-benzo[c][2,1]benzothiazine 5,5-dioxide
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: CEUALMXHHWXXSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对甲苯硫酰苯胺 在 silver(II) acetate 、 potassium tert-butylate 、 palladium diacetate 、 溶剂黄146 、 三甲基乙酸 作用下， 反应 12.0h， 以78%的产率得到2-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide
  参考文献：
  名称：

  A高效多相铜催化浐榄耦合与芳基硼酸导致磺酰叠氮化物的反应Ñ -arylsulfonamides †

  摘要：

  在室温下，在存在10 mol％的L-脯氨酸官能化的MCM-41固定化铜（I）络合物[MCM-41– L]的情况下，在MeOH中实现了磺酰叠氮化物与芳基硼酸之间的异质Chan-Lam偶联反应-脯氨酸–CuCl ]在空气中产生多种N-芳基磺酰胺，收率极高。新的多相铜络合物可以由市售的廉价试剂制备，并通过简单过滤反应溶液进行回收，并循环至少8次而不会降低活性。

  DOI：

  10.1039/c6ra04298h

文献信息

• Palladium-Catalyzed Intramolecular Oxidative Coupling Involving Double C(sp²)–H Bonds for the Synthesis of Annulated Biaryl Sultams
  作者：Joydev K. Laha、Krupal P. Jethava、Neetu Dayal

  DOI：10.1021/jo5011334

  日期：2014.9.5

  The palladium-catalyzed intramolecular oxidative coupling described herein involves a double C(sp2)–H bond functionalization in sulfonanilides, providing a workable access to biaryl sultams annulated into a six-membered ring that are otherwise difficult to obtain by literature methods. The other synthetic applications of this protocol including the synthesis of biaryl sultams containing a seven-membered

  本文所述的钯催化的分子内氧化偶合涉及磺酰苯胺中的双C（sp 2）-H键官能化，提供了可操作的途径，可将成环成六元环的联芳基均聚物，否则难以通过文献方法获得。还介绍了该协议的其他合成应用，包括合成包含七元环的类似物磺内酯和类似的磺内酯。
• 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
  作者：Atsushi Ryokawa、Hideo Togo

  DOI：10.1016/s0040-4020(01)00560-9

  日期：2001.7

  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.
• A highly efficient heterogeneous copper-catalyzed Chan–Lam coupling reaction of sulfonyl azides with arylboronic acids leading to N-arylsulfonamides
  作者：Chongren You、Fang Yao、Tao Yan、Mingzhong Cai

  DOI：10.1039/c6ra04298h

  日期：——

  A heterogeneous Chan–Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an L-proline-functionalized MCM-41-immobilized copper(I) complex [MCM-41–L-proline–CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily

  在室温下，在存在10 mol％的L-脯氨酸官能化的MCM-41固定化铜（I）络合物[MCM-41– L]的情况下，在MeOH中实现了磺酰叠氮化物与芳基硼酸之间的异质Chan-Lam偶联反应-脯氨酸–CuCl ]在空气中产生多种N-芳基磺酰胺，收率极高。新的多相铜络合物可以由市售的廉价试剂制备，并通过简单过滤反应溶液进行回收，并循环至少8次而不会降低活性。