3-(p-methoxyphenyl)-4H-1,4-benzothiazine 1,1-dioxide | 76148-83-9

• 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: 3-(p-methoxyphenyl)-4H-1,4-benzothiazine 1,1-dioxide
• 英文别名: 3-(4-methoxyphenyl)-4H-1,4-benzothiazine 1,1-dioxide；3-(4-methoxyphenyl)-4H-1lambda6,4-benzothiazine 1,1-dioxide；3-(4-methoxyphenyl)-4H-1λ6,4-benzothiazine 1,1-dioxide
• CAS: 76148-83-9
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: BQBIRGAVASSYEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氟苯硫酚 在 [Rh(OH)(cod)]2 、 sodium carbonate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 32.0h， 生成 3-(p-methoxyphenyl)-4H-1,4-benzothiazine 1,1-dioxide
  参考文献：
  名称：

  Use of (Z)-β-(2-Fluorobenzenesulfonyl)vinylamines as Novel Synthons in the Synthesis of 1,4-Benzothiazine Derivatives

  摘要：

  A novel synthetic route for arylated 1,4-benzothiazine derivatives has been developed. This method utilizes a key intramolecular nucleophilic aromatic substitution step of the corresponding (Z)-beta-(2-fluorobenzenesulfonyl) vinylamine intermediate to construct the benzothiazine ring. A wide range of aryl and heteroaryl substituent groups can be installed from commercial boronic acids. Both mono-and diarylated products have been synthesized in good yields and with good functional group tolerance.

  DOI：

  10.1055/s-0031-1289741

文献信息

• High yield synthesis of 4<i>H</i>-1,4-benzothiazine-1,1-dioxide derivatives
  作者：Stefania De Montis、Claudia Fattuoni、Enzo Cadoni、Maria G. Cabiddu、Michele Usai、Salvatore Cabiddu

  DOI：10.1002/jhet.5570450530

  日期：2008.9

  4H-1,4-Benzothiazine-1,1-dioxide derivatives were synthesized through a sequence of almost quantitative reactions. The commercial starting material 2-(methylsulfanyl)aniline was Boc-protected, N-acylated and oxidized at the sulfur atom to obtain a sulfonyl derivative. An anionic transposition of the acyl group followed by asimultaneous deprotection-cyclization gave the title products in excellent yields

  通过一系列几乎定量的反应合成了4 H -1,4-苯并噻嗪-1,1-二氧化物衍生物。将商品原料2-（甲基硫烷基）苯胺进行Boc保护，N-酰化并在硫原子上氧化以获得磺酰基衍生物。酰基的阴离子转座，然后同时进行脱保护-环化，可以以优异的收率得到标题产物。所有产品和中间体均经过充分表征。
• MacKenzie, Neil E.; Thomson, Ronald H.; Greenhalgh, Colin W., Journal of the Chemical Society. Perkin transactions I, 1980, p. 2923 - 2932
  作者：MacKenzie, Neil E.、Thomson, Ronald H.、Greenhalgh, Colin W.

  DOI：——

  日期：——
• MACKENZIE N. E.; THOMSON R. H.; GREENHAIGH C. W., J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 12, 2923-2932
  作者：MACKENZIE N. E.、 THOMSON R. H.、 GREENHAIGH C. W.

  DOI：——

  日期：——
• Use of (Z)-β-(2-Fluorobenzenesulfonyl)vinylamines as Novel Synthons in the Synthesis of 1,4-Benzothiazine Derivatives
  作者：Mark Lautens、Gavin Tsui、Yuttapong Singjunla

  DOI：10.1055/s-0031-1289741

  日期：2012.5

  A novel synthetic route for arylated 1,4-benzothiazine derivatives has been developed. This method utilizes a key intramolecular nucleophilic aromatic substitution step of the corresponding (Z)-beta-(2-fluorobenzenesulfonyl) vinylamine intermediate to construct the benzothiazine ring. A wide range of aryl and heteroaryl substituent groups can be installed from commercial boronic acids. Both mono-and diarylated products have been synthesized in good yields and with good functional group tolerance.