2,2-dichloro-1-p-tolylsulfonylethenyl isothiocyanate | 147622-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dichloro-1-p-tolylsulfonylethenyl isothiocyanate
• 英文别名: 1-tosyl-2,2-dichloroethenyl isothiocyanate；2,2-dichloro-1-tosylethenyl isothiocyanate；1-tosyl-2,2-dichloroethenylisothiocyanate；1-[(2,2-Dichloro-1-isothiocyanatovinyl)sulfonyl]-4-methylbenzene；1-(2,2-dichloro-1-isothiocyanatoethenyl)sulfonyl-4-methylbenzene
• CAS: 147622-09-1
• 化学式: C₁₀H₇Cl₂NO₂S₂
• mdl: MFCD00548049
• 分子量: 308.209
• InChiKey: BMRVXVHHOAQEFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-1-p-tolylsulfonylethenyl isothiocyanate 在 吡啶 、 双氧水 、 溶剂黄146 作用下， 以 水 、 苯 为溶剂， 反应 49.0h， 生成 4-tosyl-2-p-tolylsulfonyl-5-chloro-1,3-thiazole
  参考文献：
  名称：

  摘要：

  Treatment of 1-tosyl-2,2-dichloroethenyl isothiocyanate with alcohols, thiols, primary and secondary amines, hydrazine and its derivatives, and phosphonium ylides results in addition of the O-, S-, N-, or C-nucleophilic center to the isothiocyanate, group, followed by cyclocondensation with elimination of hydrogen chloride and formation of the corresponding 2-functionally substituted 4-tosyl-5-chloro-1,3-thiazoles. Further transformations of these compounds were studied, and a series of previously unknown types of 3-functionally substituted 1,3-thiazole derivatives were prepared.

  DOI：

  10.1023/a:1023337112138

文献信息

• Transformations of 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole
  作者：K. V. Turov、T. K. Vinogradova、B. S. Drach

  DOI：10.1134/s1070363208110248

  日期：2008.11

  Accessible 2,2-dichloro-1-p-tolylsulfonylethenyl isothiocyanate reacted with hydrazine hydrate to give 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole whose reactions with thiols and amines followed a complicated pattern. Treatment of 5-chloro-2-hydrazino-4-p-tolylsulfonyl-1,3-thiazole with acetylacetone led to the formation of previously unknown 5-chloro-2-(3,5-dimethyl-1H-pyrazol-1-yl)-4-p-tolylsulfonyl-1,3-thiazole which reacted with O-, S-, and N-centered nucleophiles at the C(5) atom with high regioselectivity.
• Reaction of 2-(Benzenesulfonyl)-5-(p-chlorobenzenesulfonyl)-4-tosyl-1,3-thiazole with O-, N-, S-, and C-nucleophiles
  作者：K. V. Turov、B. S. Drach

  DOI：10.1134/s1070363208040208

  日期：2008.4

  2-(Benzenesulfonyl)-4-tosyl-1,3-thiazole was synthesized starting from the available 2,2-dichloro-1-tosylethenyl isothiocyanate. The product is a pronounced electrophilic substrate feasible for investigation of the order of nucleophilic substitution at the C(2), C(4), and C(5) centers of the thiazole ring. Different nucleophilic agent first attack the C(2) atom. After that S-nucleophiles react with C(5), while O- and N-nucleophiles, with C(4).
• Convenient approach to the synthesis of enamino-substituted thiazoles
  作者：A. A. Tolmachev、V. S. Zyabrev、N. V. Lysenko、B. S. Drach

  DOI：10.1007/bf02256857

  日期：2000.1
• Synthesis of 4-tosyl-5-chloro-1,3-thiazole-2-carbonitrile and its transformations
  作者：K. V. Turov、T. K. Vinogradova、B. S. Drach

  DOI：10.1134/s1070363210010159

  日期：2010.1

  Reaction of the available 1-tosyl-2,2-dichloroethenyl isothiocyanate with sodium cyanide yields new clearly electrophilic substrate of thiazole nature containing the nitrile group, the tosyl residue, and the chlorine atom at C(2), C(4), and C(5) respectively. The direction of the reaction of this substrate with nucleophile depends significantly on the nature of the latter. It was used in regioselective syntheses of a series of the unknown previously trifunctional thiazoles.
• 10.1134/s1070363214110401
  作者：Kornienko、Zyabrev、Brovarets

  DOI：10.1134/s1070363214110401

  日期：——