4-chloro-N-(4,5,6,7-tetrahydro-1,2-benzothiazol-2-ium-2-yl)benzenecarboximidate | 135826-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-chloro-N-(4,5,6,7-tetrahydro-1,2-benzothiazol-2-ium-2-yl)benzenecarboximidate
• CAS: 135826-42-5
• 化学式: C₁₄H₁₃ClN₂OS
• 分子量: 292.789
• InChiKey: GGUOLWJIQDARSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(4,5,6,7-tetrahydro-1,2-benzothiazol-2-ium-2-yl)benzenecarboximidate 在 高氯酸 作用下， 反应 1.0h， 以90%的产率得到4-chloro-N-(4,5,6,7-tetrahydro-1,2-benzothiazol-2-ium-2-yl)benzamide;perchlorate
  参考文献：
  名称：

  Synthese neuer N-Aroylisothiazol-2-imine und N-Aroylamino-isothiazoliumsalze durch Cyclisierung von thiocyanato-substituierten Hydrazonen

  摘要：

  The synthesis of new N-aroylisothiazole-2-imines (4g-n) as well as the corresponding acceptor-substituted 2-amino-isothiazolium salts (6f-n) by cyclocondensation of thiocyanatovinylaldehyde hydrazones (3) is reported. The structure of these N-imines was proved by spectroscopic methods. The alternative cyclization route to 1,2,3-thiadiazines (8) is not observed. The hydrazones (3a-e) could not be cyclized to N-imines, only sulfides (5a-c) were obtained. The reaction of 2-thiocyanatomethylen-cycloheptan-2-one (9) with benzhydrazides gave the same ring closure to the salts (10a,b). The structure of the N-imine 11b has been confirmed unequivocally by X-ray structure analysis.

  DOI：

  10.1002/prac.19943360204
• 作为产物：
  描述：

  2-thiocyanato-cyclohex-1-enecarbaldehyde 、 4-氯苯甲酰肼 以 乙醇 、 水 为溶剂， 反应 1.0h， 以71%的产率得到4-chloro-N-(4,5,6,7-tetrahydro-1,2-benzothiazol-2-ium-2-yl)benzenecarboximidate
  参考文献：
  名称：

  Synthese neuer N-Aroylisothiazol-2-imine und N-Aroylamino-isothiazoliumsalze durch Cyclisierung von thiocyanato-substituierten Hydrazonen

  摘要：

  The synthesis of new N-aroylisothiazole-2-imines (4g-n) as well as the corresponding acceptor-substituted 2-amino-isothiazolium salts (6f-n) by cyclocondensation of thiocyanatovinylaldehyde hydrazones (3) is reported. The structure of these N-imines was proved by spectroscopic methods. The alternative cyclization route to 1,2,3-thiadiazines (8) is not observed. The hydrazones (3a-e) could not be cyclized to N-imines, only sulfides (5a-c) were obtained. The reaction of 2-thiocyanatomethylen-cycloheptan-2-one (9) with benzhydrazides gave the same ring closure to the salts (10a,b). The structure of the N-imine 11b has been confirmed unequivocally by X-ray structure analysis.

  DOI：

  10.1002/prac.19943360204

文献信息

• Kolberg, Arne; Kirrbach, Sabine; Selke, Dagmar, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 3, p. 291 - 296
  作者：Kolberg, Arne、Kirrbach, Sabine、Selke, Dagmar、Schulze, Baerbel、Morozkina, Svetlana

  DOI：——

  日期：——
• Synthese neuer N-Aroylisothiazol-2-imine und N-Aroylamino-isothiazoliumsalze durch Cyclisierung von thiocyanato-substituierten Hydrazonen
  作者：B�rbel Schulze、Dagmar Selke、Sabine Kirrbach、Rhett Kempe

  DOI：10.1002/prac.19943360204

  日期：——

  The synthesis of new N-aroylisothiazole-2-imines (4g-n) as well as the corresponding acceptor-substituted 2-amino-isothiazolium salts (6f-n) by cyclocondensation of thiocyanatovinylaldehyde hydrazones (3) is reported. The structure of these N-imines was proved by spectroscopic methods. The alternative cyclization route to 1,2,3-thiadiazines (8) is not observed. The hydrazones (3a-e) could not be cyclized to N-imines, only sulfides (5a-c) were obtained. The reaction of 2-thiocyanatomethylen-cycloheptan-2-one (9) with benzhydrazides gave the same ring closure to the salts (10a,b). The structure of the N-imine 11b has been confirmed unequivocally by X-ray structure analysis.