3-Benzyl-5-(tert-butylamino)-4-(dimethylamino)-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-(dimethylamino)-2-(phenylthio)thiazolium chloride
• 英文别名: 3-benzyl-5-N-tert-butyl-4-N,4-N-dimethyl-2-phenylsulfanyl-1,3-thiazol-3-ium-4,5-diamine;chloride
• 化学式: C₂₂H₂₈N₃S₂*Cl
• 分子量: 434.069
• InChiKey: OFQFGRREMIOHKJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Benzyl-5-(tert-butylamino)-4-(dimethylamino)-2-(phenylthio)thiazolium chloride 在 敌草腈 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以38%的产率得到3-Benzyl-5-(tert-butylimino)-2-(phenylthio)-4-thiazolidinone
  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
• 作为产物：
  描述：

  苄异腈 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-Benzyl-5-(tert-butylamino)-4-(dimethylamino)-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

• Base-induced conversion of 5-aminothiazolium salts into substituted pyrroles and pyrrolines via 1,3-dipolar cycloadditions with electron-deficient alkynes and alkenes
  作者：Fabienne Berrée、Georges Morel

  DOI：10.1016/0040-4020(95)00359-g

  日期：1995.6

  base-catalyzed rearrangements of the primary 1 : 1 cycloadducts, with retention of the elements of isothiocyanate. A similar initial cycloadduct 17 was isolated from N-phenylmaleimide which generally led to the condensed imino thiopyrans 20. Some of the 1,3-dipolar reactional stereoselectivities were deduced from the stereochemistry or distribution of the final products and found to be markedly dependent

  在DBN或NEt 3的存在下，通过用几种亲电性偶极亲和剂处理5-氨基噻唑鎓盐1，生成了一系列中离子噻唑2并就地转化。反应涉及“掩蔽的”环状偶氮甲亚胺的1，3-偶极环加成反应跨烯烃或乙炔π键，作为第一步，产生不稳定的N桥联加合物。因此，DMAD和丙酸甲酯通过随后的异硫氰酸酯的挤出得到官能化的吡咯。富马酸二甲酯，马来酸酯和富马腈通过碱催化的主要1：1环加合物的重排，保留了异硫氰酸酯的元素，提供了多种多取代的吡咯啉，吡咯和氨基丁二烯。类似的初始环加合物从N-苯基马来酰亚胺中分离出17，其通常导致缩合的亚氨基硫代吡喃20。从最终产物的立体化学或分布推导了一些1，3-偶极反应性立体选择性，发现它们明显取决于存在的取代基。