3-(4-(trifluoromethyl)phenyl)-4H-1,4-benzothiazine 1,1-dioxide | 1384585-89-0

• 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-(4-(trifluoromethyl)phenyl)-4H-1,4-benzothiazine 1,1-dioxide
• 英文别名: 3-[4-(trifluoromethyl)phenyl]-4H-1lambda6,4-benzothiazine 1,1-dioxide；3-[4-(trifluoromethyl)phenyl]-4H-1λ6,4-benzothiazine 1,1-dioxide
• CAS: 1384585-89-0
• 化学式: C₁₅H₁₀F₃NO₂S
• 分子量: 325.311
• InChiKey: AQBVISIDEFBNDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

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-(4-(trifluoromethyl)phenyl)-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

• One-Pot Domino Reaction: Direct Access to Polysubstituted 1,4-Benzothiazine 1,1-Dioxide via Water–Gas Shift Reaction Utilizing DMF/H₂O
  作者：Yogesh Sharma、Ganesh P. Pawar、Vinod D. Chaudhari

  DOI：10.1021/acs.joc.2c02171

  日期：2023.1.6

  Benzothiazine 1,1-dioxide (BTDO) is a privileged chemical motif, and its metal-free domino access is in high demand. Current BTDO production methods require costly metal catalysts or harsh reaction conditions. A facile domino approach to BTDO via a water–gas shift reaction (WGSR) employing sodium 2-nitrobenzenesulfinates and α-bromo ketones is presented. This strategy is cost-effective and environmentally

  苯并噻嗪 1,1-二氧化物 (BTDO) 是一种特殊的化学基序，其无金属多米诺骨牌通道的需求量很大。目前的 BTDO 生产方法需要昂贵的金属催化剂或苛刻的反应条件。提出了一种通过使用 2-硝基苯亚磺酸钠和 α-溴酮的水煤气变换反应 (WGSR) 生成 BTDO 的简单多米诺骨牌方法。该策略具有成本效益且对环境有益。优化的反应条件对两个偶联伙伴上的各种电学和空间变化的取代基表现出显着的化学耐受性。
• 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.