3-Benzyl-5-(tert-butylamino)-4-phenyl-2-(phenylthio)thiazolium chloride

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-Benzyl-5-(tert-butylamino)-4-phenyl-2-(phenylthio)thiazolium chloride
• 英文别名: 3-benzyl-N-tert-butyl-4-phenyl-2-phenylsulfanyl-1,3-thiazol-3-ium-5-amine;chloride
• 化学式: C₂₆H₂₇N₂S₂*Cl
• 分子量: 467.099
• InChiKey: AFPGQIWHUKYTNA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Benzyl-5-(tert-butylamino)-4-phenyl-2-(phenylthio)thiazolium chloride 在 苯硫酚 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 28.0h， 以86%的产率得到1-Benzyl-3-tert-butyl-5-phenylimidazol-3-ium-4-thiolate
  参考文献：
  名称：

  2-未取代的咪唑鎓盐和噻唑鎓盐的新型便捷方法

  摘要：

  高度官能化的 5-(叔丁基氨基)-2-(苯硫基)噻唑鎓氯化物和介离子 2-(苯硫基)噻唑鎓-5-硫醇盐的选择性还原裂解在室温下使用过量的 PhSH 在Et 3 N得到相应的2-未取代咪唑鎓和噻唑鎓-5-硫醇盐。还报道了 2-(甲硫基)咪唑氯化物的 NaBH 4 还原和噻唑啉-2-硫酮的 H 2 O 2 处理。

  DOI：

  10.1055/s-2003-42100
• 作为产物：
  描述：

  氯代二硫代甲酸苯基酯 、 异氰酸叔丁酯 、 N-苄烯丁胺 以 氯仿 为溶剂， 反应 9.0h， 以61%的产率得到3-Benzyl-5-(tert-butylamino)-4-phenyl-2-(phenylthio)thiazolium chloride
  参考文献：
  名称：

  Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates

  摘要：

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.

  DOI：

  10.1021/jo00074a032

文献信息

• Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates
  作者：Fabienne Berree、Yvelise Malvaut、Evelyne Marchand、Georges Morel

  DOI：10.1021/jo00074a032

  日期：1993.10

  Treatment of imino chloro sulfides with dimethylthioformamide and isocyanides at room temperature provides selectively the 5-amino-4-(dimethylamino)-2-(methylthio)(or phenylthio)thiazolium salts. Similarly, the reactions of p-tolyl chlorothionoformate and phenyl chlorodithioformate with a mixture of benzaldimine and isocyanide afford rapidly the 5-amino-4-phenylthiazolium salts. We suggest that these reactions involve the N-(thiocarbonyl)formamidinium and benzylideniminium chlorides as transient intermediates, which are trapped by isocyanides according to a [1 + 4] cycloaddition process. The structure of the thiazolium salts and some of their reactivities are discussed.
• A Novel and Convenient Approach to 2-Unsubstituted Imidazolium and Thiazolium Salts
  作者：Georges Morel

  DOI：10.1055/s-2003-42100

  日期：——

  The selective reductive cleavage of highly functionalized 5-(tert-butylamino)-2-(phenylthio)thiazolium chlorides and mesoionic 2-(phenylthio)thiazolium-5-thiolates has been effected efficiently at room temperature using an excess of PhSH in the presence of Et 3 N to give the corresponding 2-unsubstituted imidazolium and thiazolium-5-thiolates. The NaBH 4 reduction of 2-(methylthio)imidazolium chlorides

  高度官能化的 5-(叔丁基氨基)-2-(苯硫基)噻唑鎓氯化物和介离子 2-(苯硫基)噻唑鎓-5-硫醇盐的选择性还原裂解在室温下使用过量的 PhSH 在Et 3 N得到相应的2-未取代咪唑鎓和噻唑鎓-5-硫醇盐。还报道了 2-(甲硫基)咪唑氯化物的 NaBH 4 还原和噻唑啉-2-硫酮的 H 2 O 2 处理。