6H-10-trifluoromethylquino[3,2-b]benzo[1,4]thiazine | 1192303-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6H-10-trifluoromethylquino[3,2-b]benzo[1,4]thiazine
• 英文别名: 10-trifluoromethylquinobenzothiazine；6H-10-trifluoromethylquinobenzothiazine；10-(trifluoromethyl)-6H-quinolino[3,2-b][1,4]benzothiazine
• CAS: 1192303-54-0
• 化学式: C₁₆H₉F₃N₂S
• 分子量: 318.322
• InChiKey: XSPCTABXAONSAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6H-10-trifluoromethylquino[3,2-b]benzo[1,4]thiazine 、 氯化苄 在 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 25.0h， 以86%的产率得到6-benzyl-10-trifluoromethylquino[3,2-b]benzothiazine
  参考文献：
  名称：

  The Structures of 8- and 10-Trifluoromethylquino[3,2-b]benzo[1,4]thiazines and Their Benzyl Derivatives

  摘要：

  The modification of the phenothiazine structure via the substitution of the benzene ring with the quinoline ring may proceed through the Ullmann cyclization or the Smiles rearrangement of the appropriate sulfides followed by cyclization. Reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide or pentacyclic diquinodithiin with m-trifluoromethylaniline led to two isomeric tetracyclic trifluoromethylquinobenzothiazines. The product structures as the appropriate 6H-X-trifluoromethylquino[3,2-b]benzo[1,4]thiazines (X = 8, 10) were finally confirmed by X-ray analysis (one product was transformed into N-benzyl derivative). These results exclude the possibility of the reverse Smiles rearrangement and the existence of 5H-tautomers in these conditions. Although both compounds have the same quinobenzothiazine system, they differ in the spatial structures and geometric data. Molecule 6b is unexpectedly almost planar that is the result of larger than usual the C-S-C and C-N-C angles in the thiazine ring. Molecule 14 is folded along the S-N axis with the thiazine ring in boat conformation and the benzyl group in equatorial position.

  DOI：

  10.3987/com-12-12528
• 作为产物：
  描述：

  5,12-diaza-6,13-dithiapentacene 、 3-(三氟甲基)苯胺盐酸盐 反应 4.0h， 以28%的产率得到6H-8-trifluoromethylquino[3,2-b]benzo[1,4]thiazine
  参考文献：
  名称：

  Diquino-1,4-dithiin 和 2,2'-Dichloro-3,3'-diquinolinyl Disulfide 合成 Quinobenzo-1,4-thiazines

  摘要：

  合成新型四环氮杂吩噻嗪，6-, 8-, 9- 和 10-取代的 quinobenzo-1,4-thiazines (benzo[b]-1-azaphenothiazines) (5) 和 (10), 从diquino-1,4-dithiin (5,12-diaza-6,13-​​dithiapentacene) (2) 通过 1,4-dithiin 开环和 1,4-thiazine 与盐酸苯胺 (8)·HCl 发生融合反应闭环。当 2,2'-二氯-3,3'-二喹啉基二硫化物 (9) 与苯胺 (8) 在 MEDG 中反应时，获得了更好的结果。选择的 6H-quinobenzo-1,4-thiazines (5a) (5c) 和 (5g) 通过使用烷基卤化物的 N-烷基化转化为 6-烷基衍生物 (10a-10n)。6-甲基衍生物（10a）的同核NOE实验证实产物结构为醌[3,2-b]苯并[1,4]噻嗪。

  DOI：

  10.3987/com-09-11736

文献信息

• Synthesis of Quinobenzo-1,4-thiazines from Diquino-1,4-dithiin and 2,2’-Dichloro-3,3’-diquinolinyl Disulfide
  作者：Krystian Pluta、Małgorzata Jeleń

  DOI：10.3987/com-09-11736

  日期：——

  10-substituted quinobenzo-1,4-thiazines (benzo[b]-1-azaphenothiazines) (5) and (10), has been worked out from diquino-1,4-dithiin (5,12-diaza-6,13-dithiapentacene) (2) as fusion reactions with aniline hydrochlorides (8)·HCl via the 1,4-dithiin ring opening and the 1,4-thiazine ring closure. The better results were obtained when 2,2'-dichloro-3,3'-diquinolinyl disulfide (9) reacted with anilines (8) in MEDG

  合成新型四环氮杂吩噻嗪，6-, 8-, 9- 和 10-取代的 quinobenzo-1,4-thiazines (benzo[b]-1-azaphenothiazines) (5) 和 (10), 从diquino-1,4-dithiin (5,12-diaza-6,13-​​dithiapentacene) (2) 通过 1,4-dithiin 开环和 1,4-thiazine 与盐酸苯胺 (8)·HCl 发生融合反应闭环。当 2,2'-二氯-3,3'-二喹啉基二硫化物 (9) 与苯胺 (8) 在 MEDG 中反应时，获得了更好的结果。选择的 6H-quinobenzo-1,4-thiazines (5a) (5c) 和 (5g) 通过使用烷基卤化物的 N-烷基化转化为 6-烷基衍生物 (10a-10n)。6-甲基衍生物（10a）的同核NOE实验证实产物结构为醌[3,2-b]苯并[1,4]噻嗪。
• The Structures of 8- and 10-Trifluoromethylquino[3,2-b]benzo[1,4]thiazines and Their Benzyl Derivatives
  作者：Krystian Pluta、Małgorzata Jeleń、Kinga Suwińska、Céline Besnard、Beata Morak-Młodawska

  DOI：10.3987/com-12-12528

  日期：——

  The modification of the phenothiazine structure via the substitution of the benzene ring with the quinoline ring may proceed through the Ullmann cyclization or the Smiles rearrangement of the appropriate sulfides followed by cyclization. Reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide or pentacyclic diquinodithiin with m-trifluoromethylaniline led to two isomeric tetracyclic trifluoromethylquinobenzothiazines. The product structures as the appropriate 6H-X-trifluoromethylquino[3,2-b]benzo[1,4]thiazines (X = 8, 10) were finally confirmed by X-ray analysis (one product was transformed into N-benzyl derivative). These results exclude the possibility of the reverse Smiles rearrangement and the existence of 5H-tautomers in these conditions. Although both compounds have the same quinobenzothiazine system, they differ in the spatial structures and geometric data. Molecule 6b is unexpectedly almost planar that is the result of larger than usual the C-S-C and C-N-C angles in the thiazine ring. Molecule 14 is folded along the S-N axis with the thiazine ring in boat conformation and the benzyl group in equatorial position.