1-oxo-3-phenyl-2H-1,2,4-benzothiadiazine | 4826-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 1-oxo-3-phenyl-2H-1,2,4-benzothiadiazine
• 英文别名: 3-phenyl-2(4)H-benzo[1,2,4]thiadiazine 1-oxide；3-Phenyl-2H-1,2,4-benzothiadiazin-oxid-(1)
• CAS: 4826-05-5
• 化学式: C₁₃H₁₀N₂OS
• 分子量: 242.301
• InChiKey: QPQKICQXTOOCPK-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C (decomp)(Solv: dichloromethane (75-09-2))
• 沸点：
  458.9±28.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-oxo-3-phenyl-2H-1,2,4-benzothiadiazine 在 溶剂黄146 、 锌 作用下， 生成 2-苯基苯并噻唑
  参考文献：
  名称：

  Kresze,G. et al., Justus Liebigs Annalen der Chemie, 1968, vol. 715, p. 223 - 237

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methanesulfonylamino-3-phenyl-1λ⁴-benzo[1,2,4]thiadiazine 在 溶剂黄146 作用下， 生成 1-oxo-3-phenyl-2H-1,2,4-benzothiadiazine
  参考文献：
  名称：

  Kresze,G. et al., Justus Liebigs Annalen der Chemie, 1968, vol. 715, p. 223 - 237

  摘要：

  DOI：

文献信息

• Copper-promoted aerial oxidation of benzothiadiazines: access to benzothiadiazine S-oxide heterocycles
  作者：Ewan R. Clark、John J. Hayward、Bryce J. Leontowicz、Muhammad U. Anwar、Melanie Pilkington、Jeremy M. Rawson

  DOI：10.1039/c4dt03467h

  日期：——

  Aerial oxidation of benzothiadiazines selectively affords the corresponding benzothiadiazine S-oxides in the presence of Cu²⁺ ions. Structural studies reveal that the S-oxide appears to be a strong hydrogen-bond acceptor.

  苯并噻二嗪的空气氧化在Cu2+离子的存在下选择性地生成相应的苯并噻二嗪S-氧化物。结构研究表明，S-氧化物似乎是一个强的氢键受体。
• 1-Oxo-1-fluoro-1,2,4-benzothiadiazines—A new type of cyclic sulfonimidoyl fluorides
  作者：Natalia P. Kolesnik、Alexander B. Rozhenko、Vasyl Kinzhybalo、Tadeusz Lis、Yuriy G. Shermolovich

  DOI：10.1016/j.jfluchem.2014.01.008

  日期：2014.4

  An approach to the synthesis of the novel cyclic sulfonimidoyl fluorides was elaborated based on the electrophilic fluorination of 1-oxo-2H-1,2,4-benzothiadizines with Selectfluor®. Crystal structure of 1-oxo-1-fluoro-3-phenyl-1,2,4-benzothiadiazine was determined.

  到新的环状sulfonimidoyl氟化物的合成的方法得到阐述基于1-氧代-2H-1,2,4- benzothiadizines用的Selectfluor的电氟化®。测定了1-氧代-1-氟-3-苯基-1,2,4-苯并噻二嗪的晶体结构。
• Syntheses of 1,2,4-benzothiadiazine 1-oxides and 1,2,4-benzothiadiazines
  作者：Neville Finch、Salvatore Ricca、Lincoln H. Werner、Ronald Rodebaugh

  DOI：10.1021/jo01305a009

  日期：1980.8
• Markovskii,L.N.; Darmokhval,E.A., Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, # 3, p. 664 - 665
  作者：Markovskii,L.N.、Darmokhval,E.A.

  DOI：——

  日期：——
• Experimental and Theoretical Studies of Fused-Ring Persistent [1,2,4]Thiadiazinyl Radicals
  作者：Józef Zienkiewicz、Piotr Kaszynski、Victor G. Young

  DOI：10.1021/jo0486746

  日期：2004.10.1

  Five persistent radicals la-le were generated by the oxidation of 4H-[1,2,4]thiadiazines 2a-2e and studied with ESR and UV-vis spectroscopy. Three of the radicals, 1a, 1d, and 1e, were generated in high yields (>90%) using either SO2Cl2/amine in toluene or AgO/K2CO3 in a toluene/MeCN mixture. Halogenated radicals 1d and le were sufficiently stable for chromatographic isolation and vacuum sublimation. The solution stability of the fluorinated 1d was measured at t(1/2) approximate to 4 months in the absence of oxygen, and le at t(1/2) approximate to 40 min in the presence of air. The crystal and molecular structures of 1d were determined by X-ray crystallography showing columns of parallel almost evenly spaced planar heterocycles connected by infinite ...N...S... chains. Cyclic voltammetry of 1d and le shows reversible reduction waves at about 0 V and irreversible oxidations at about 1.2 V. Spectral and electrochemical properties of 1 were well reproduced by DFT methods.