5-(tert-Butylamino)-3-methyl-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: 5-(tert-Butylamino)-3-methyl-4-phenyl-2-(phenylthio)thiazolium chloride
• 英文别名: N-tert-butyl-3-methyl-4-phenyl-2-phenylsulfanyl-1,3-thiazol-3-ium-5-amine;chloride
• 化学式: C₂₀H₂₃N₂S₂*Cl
• 分子量: 391.001
• InChiKey: NWXLALWZXRFBHE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  5-(tert-Butylamino)-3-methyl-4-phenyl-2-(phenylthio)thiazolium chloride 在 三乙胺 作用下， 以 四氢呋喃 、 氘代氯仿 为溶剂， 反应 14.0h， 生成 1,2-bis[1-methyl-2-phenyl-5-(phenylthio)-4-thiolate-imidazolium-3-yl]phenyl
  参考文献：
  名称：

  在α-硫代硫代酰胺或介离子噻唑存在下，二异硫氰酸酯作为亲异二烯体或亲偶极体

  摘要：

  进行 α-硫代硫代酰胺 (1) 与二异硫氰酸酯的反应，希望生成 N,N'-双 (1,3-噻唑啉-2-硫酮) (A)。尽管该目的无法实现，但我们成功地从亚苯基-1,2-二异硫氰酸酯 (4) 制备了单环加合物 7。苯并咪唑衍生物 8 和 9 也被表征，并假设一种机制来解释这种分子内过程。另一方面，通过在碱性介质中用二异硫氰酸酯 (4) 处理 5-氨基噻唑鎓氯化物 (2) 进行含有亚苯基桥的 N,N'-联咪唑 (13) 的区域选择性合成。介离子衍生物 13 可能来自单咪唑鎓-4-硫醇盐 (12)，它显示在类似条件下与盐 2 反应，得到初级环加合物 14 作为双（咪唑鎓）（13）的中间体。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:617–624, 2001

  DOI：

  10.1002/hc.1093
• 作为产物：
  描述：

  氯代二硫代甲酸苯基酯 、 异氰酸叔丁酯 、 苯亚甲基甲胺 以 氯仿 为溶剂， 反应 5.0h， 以81%的产率得到5-(tert-Butylamino)-3-methyl-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

• 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。
• 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。
• 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.
• Diisothiocyanates as heterodienophiles or dipolarophiles in the presence of ?-thioxothioamides or mesoionic thiazoles
  作者：Georges Morel、Evelyne Marchand

  DOI：10.1002/hc.1093

  日期：——

  Reactions of α-thioxothioamides (1) with diisothiocyanates were carried out in the hope of generating the N,N′-bis(1,3-thiazoline-2-thiones) (A). Although that purpose could not be achieved, we succeeded in preparing the monocycloadducts 7 from the phenylene-1,2-diisothiocyanate (4). The benzimidazole derivatives 8 and 9 were also characterized and a mechanism was assumed to account for this intramolecular

  进行 α-硫代硫代酰胺 (1) 与二异硫氰酸酯的反应，希望生成 N,N'-双 (1,3-噻唑啉-2-硫酮) (A)。尽管该目的无法实现，但我们成功地从亚苯基-1,2-二异硫氰酸酯 (4) 制备了单环加合物 7。苯并咪唑衍生物 8 和 9 也被表征，并假设一种机制来解释这种分子内过程。另一方面，通过在碱性介质中用二异硫氰酸酯 (4) 处理 5-氨基噻唑鎓氯化物 (2) 进行含有亚苯基桥的 N,N'-联咪唑 (13) 的区域选择性合成。介离子衍生物 13 可能来自单咪唑鎓-4-硫醇盐 (12)，它显示在类似条件下与盐 2 反应，得到初级环加合物 14 作为双（咪唑鎓）（13）的中间体。© 2001 John Wiley & Sons, Inc. 杂原子化学 12:617–624, 2001