3-Phenyl-5,6-dihydrothiazolo<2,3-b>thiazolium | 6094-68-4

• 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-Phenyl-5,6-dihydrothiazolo<2,3-b>thiazolium
• 英文别名: 5-Phenyl-2,3-dihydrothiazolo<2,3-b>thiazolium；3-Phenyl-5,6-dihydro-thiazolo<2.3-b>thiazoliumbromid；5-phenyl-2,3-dihydro-thiazolo[2,3-b]thiazolylium; bromide；5-Phenyl-2,3-dihydro-[1,3]thiazolo[2,3-b][1,3]thiazol-4-ium;bromide
• CAS: 6094-68-4
• 化学式: Br*C₁₁H₁₀NS₂
• 分子量: 300.243
• InChiKey: GKUNPIWAZOGBCH-UHFFFAOYSA-M

物化性质

• 熔点：
  231 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.19
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Phenyl-5,6-dihydrothiazolo<2,3-b>thiazolium 在 氢氧化钾 作用下， 生成 2-甲基-4-苯基噻唑
  参考文献：
  名称：

  Studies of heterocyclic compounds. VII. The reactions of 5,6-dihydrothiazolo(2,3-b)thiazolium salts with carbanions.

  摘要：

  5,6-二氢噻唑并[2,3-b]噻唑盐(1)与乙酰乙酸钠反应，生成3-(2-噻唑基)乙酰乙酸(2)，同时脱去硫杂环丙烷和2-丙酮亚甲基-3-乙酰硫乙基-4-噻唑啉(3)。1与乙酰乙酸乙酯钠盐反应得到乙基2-(2-噻唑基)乙酰乙酸酯(12)，而1与氰乙酸乙酯钠盐和丙二腈钠盐反应则生成2-取代噻唑(16)、3-(2-巯基乙基)噻唑啉(17)及其二硫化物(18)。根据甲基化产物的结构及其分光光度特性，讨论了2、12和16的互变异构形式。

  DOI：

  10.1248/cpb.23.3254
• 作为产物：
  描述：

  2-(Δ²-Thiazolinyl-(2)-mercapto)-acetophenon-hydrochlorid 在 氢溴酸 作用下， 生成 3-Phenyl-5,6-dihydrothiazolo<2,3-b>thiazolium
  参考文献：
  名称：

  Bradsher,C.K.; Jones,W.J., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, # 3, p. 274 - 278

  摘要：

  DOI：

文献信息

• Studies of heterocyclic compounds. V. Synthesis of 5,6-dihydrothiazolo(2,3-b)thiazolium salts and their reactions with amines. A new synthesis of 2-aminothiazoles.
  作者：HIROKO OHTSUKA、HATSUNORI TOYOFUKU、TADASHI MIYASAKA、KIICHI ARAKAWA

  DOI：10.1248/cpb.23.3234

  日期：——

  5, 6-Dihydrothiazolo [2, 3-b] thiazolium salts (1a-d) were synthesized from 2-mercapto-thiazoline and α-haloketones. The reaction of 1 with a secondary amine gave 2-aminothiazole (7a-1) with the liberation of thiirane (9) via an unstable adduct, 7a-amino-2, 3, 5, 6-tetrahydrothiazolo [2, 3-b] thiazole (8a-g). The reaction of 1 with a primary amine afforded 3-(2-mercaptoethyl)-4-thiazolin-2-imine (10) and/or its disulfide (11). The reaction of 1 with an amine was concluded to be initiated by the attack of the reagent on C-7a.

  5, 6-二氢噻唑 [2, 3-b] 噻唑鎓盐（1a-d）是通过2-巯基噻唑啉和α-卤酮合成的。1与二级胺的反应生成了2-氨基噻唑（7a-1），同时通过不稳定的加合物7a-氨基-2, 3, 5, 6-四氢噻唑 [2, 3-b] 噻唑（8a-g）释放出噻烷（9）。1与一级胺的反应产生了3-(2-巯基乙基)-4-噻唑啉-2-亚胺（10）和/或其二硫化物（11）。关于1与胺的反应，结论是反应的起始是由于试剂对C-7a的攻击。
• Studies of heterocyclic compounds. VI. The reactions of 5,6-dihydrothiazolo(2,3-b)thiazolium salts with O- and S-nucleophiles.
  作者：HIROKO OHTSUKA、TADASHI MIYASAKA、KIICHI ARAKAWA

  DOI：10.1248/cpb.23.3243

  日期：——

  The reaction of 5, 6-dihydrothiazolo [2, 3-b] thiazolium salts (1) with hydroxide ion furnished disulfide of 3-(2-mercaptoethyl)-4-thiazolin-2-one (6). The reaction of 1 with hydrogensulfide ion furnished 3-(2-mercaptoethyl)-4-thiazolin-2-thione (7) and/or its disulfide (8) and with N, N-dimethyldithiocarbamate ion furnished 3-(N, N-dimethyl-dithiocarbamylethyl)-4-thiazolin-2-thione (12) whereas the reaction of 1b with thiophenolate ion afforded 3-(2-phenylthioethyl)-4-thiazolin-2-thione (18b), thiazole (21), 6b, phenyl 2-[2-(4-phenylthiazolin-2-thion-3-yl) ethylthio] ethyl disulfide (22) and phenyl 2-phenylthioethyl disulfide (23). Brief reaction mechanism of the formation of these products are discussed. The reaction of 1 is considered to be initiated by the attack of the nucleophile on the polarized >C=N< bond to form an adduct and to proceed through AE-mechanism. The elimination stage of the reaction is concluded to depend upon basicity, polarizability and other properties of the reagent to induce either the cleavage of S7-C7a bond, the cleavage of S7-C7a and N-C5 bonds, or another attack of the reagent on C5 or on S7.

  5, 6-二氢噻唑并[2, 3-b]噻唑鎓盐(1)与氢氧根离子反应得到3-(2-巯基乙基)-4-噻唑啉-2-酮(6)的二硫化物。 1与硫氢离子反应得到3-(2-巯基乙基)-4-噻唑啉-2-硫酮(7)和/或其二硫化物(8)，与N，N-二甲基二硫代氨基甲酸根离子反应得到3-(N，N-)二甲基-二硫代氨基甲酰乙基)-4-噻唑啉-2-硫酮(12)，而1b与苯硫酚根离子的反应得到3-(2-苯硫基乙基)-4-噻唑啉-2-硫酮(18b)、噻唑(21)、6b、苯基2-[2-(4-苯基噻唑啉-2-硫磷-3-基)乙硫基]乙基二硫醚(22)和苯基2-苯硫基乙基二硫醚(23)。讨论了这些产物形成的简要反应机理。 1的反应被认为是由亲核试剂攻击极化的>C=N<键形成加合物并通过AE机制进行的。反应的消除阶段取决于试剂的碱性、极化性和其他性质，以诱导 S7-C7a 键的裂解、S7-C7a 和 N-C5 键的裂解，或试剂对C5 或 S7。
• Reaction of 2-mercaptothiazoline with α-halogenocar bonyl compounds
  作者：V. A. Bogolyubskii、L. T. Bogolyubskaya

  DOI：10.1007/bf00481589

  日期：1967.7
• OHTSUKA H.; MIYASAKA T.; ARAKAWA K., CHEM. AND PHARM. BULL. <CPBT-AL>, 1975, 23, NO 12, 3254-3265
  作者：OHTSUKA H.、 MIYASAKA T.、 ARAKAWA K.

  DOI：——

  日期：——
• Studies of heterocyclic compounds. VII. The reactions of 5,6-dihydrothiazolo(2,3-b)thiazolium salts with carbanions.
  作者：HIROKO OHTSUKA、TADASHI MIYASAKA、KIICHI ARAKAWA

  DOI：10.1248/cpb.23.3254

  日期：——

  The reaction of 5, 6-dihydrothiazolo [2, 3-b] thiazolium salt (1) with the sodium salt of acetylacetone furnished 3-(2-thiazolyl)-acetylacetone (2) with elimination of thiirane and 2-acetonylidene-3-acetylthioethyl-4-thiazoline (3). The reaction of 1 with the sodium salt of ethyl acetoacetate gave ethyl 2-(2-thiazolyl)-acetoacetate (12) and the reaction of 1 with the sodium salts of ethyl cyanoacetate and malononitrile gave 2-substituted thiazole (16), 3-(2-mercaptoethyl)-thiazoline (17) and/or its disulfide (18). The tautomeric forms of 2, 12 and 16 are discussed on the basis of the structures of the methylated products and of their spectrophotometric properties.

  5,6-二氢噻唑并[2,3-b]噻唑盐(1)与乙酰乙酸钠反应，生成3-(2-噻唑基)乙酰乙酸(2)，同时脱去硫杂环丙烷和2-丙酮亚甲基-3-乙酰硫乙基-4-噻唑啉(3)。1与乙酰乙酸乙酯钠盐反应得到乙基2-(2-噻唑基)乙酰乙酸酯(12)，而1与氰乙酸乙酯钠盐和丙二腈钠盐反应则生成2-取代噻唑(16)、3-(2-巯基乙基)噻唑啉(17)及其二硫化物(18)。根据甲基化产物的结构及其分光光度特性，讨论了2、12和16的互变异构形式。