6-benzyl-10-trifluoromethylquino[3,2-b]benzothiazine | 1403665-00-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-benzyl-10-trifluoromethylquino[3,2-b]benzothiazine
• 英文别名: 6-benzyl-10-trifluoromethylquinobenzothiazine
• CAS: 1403665-00-8
• 化学式: C₂₃H₁₅F₃N₂S
• 分子量: 408.447
• InChiKey: IPMVBEBWAWXXDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(三氟甲基)苯胺盐酸盐 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， 生成 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