2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1,3-cyclohexanedione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1,3-cyclohexanedione
• 英文别名: 2-(4-Chlorodithiazol-5-ylidene)cyclohexane-1,3-dione
• 化学式: C₈H₆ClNO₂S₂
• 分子量: 247.726
• InChiKey: KENDFTACHKNTKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 4,5-二氯-1,2,3-二噻唑氯化物 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以13%的产率得到2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-1,3-cyclohexanedione
  参考文献：
  名称：

  Synthesis of new5-alkylidene-4-chloro-5H-1,2,3-dithiazoles and their stereochemistry

  摘要：

  A variety of 5-alkylidene-4-chloro-5H-1,2,3-dithiazoles (9-25) have been prepared from 4-chloro-5H-1,2,3-dithiazolium chloride, active methylene compounds, and pyridine. The reactions with ethyl nitroacetate ((Z) > (E)), ethyl 3-nitrobenzoylacetate ((E) > (Z)), ethyl 2-fluorobenzoylacetate ((E) > (Z)), and tetronic acid ((Z) > (E)) gave a mixture of (E)- and (Z)-isomers, whereas those of benzoylnitromethane (Z), 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (E), 4-hydroxy-6-methyl-2-pyrone (E), 4-hydroxycoumarin (E), 6-chloro-4-hydroxycoumarin (E), and 6-bromo-4-hydroxycoumarin (E) afforded only single stereoisomers. The reactions with 4-hydroxy-1-methyl-2(1H)-quinolone, 2-hydroxy-1,4-naphthoquinone and homophthalic anhydride gave only single stereoisomers whose stereochemistry is uncertain. It appears that geometrically more rigid cyclic 1,3-dicarbonyl compounds give better yields of dithiazol-5-ylidenes than the corresponding acyclic compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00585-2

文献信息

• Synthesis of new5-alkylidene-4-chloro-5H-1,2,3-dithiazoles and their stereochemistry
  作者：Moon-Kook Jeon、Kyongtae Kim

  DOI：10.1016/s0040-4020(99)00585-2

  日期：1999.8

  A variety of 5-alkylidene-4-chloro-5H-1,2,3-dithiazoles (9-25) have been prepared from 4-chloro-5H-1,2,3-dithiazolium chloride, active methylene compounds, and pyridine. The reactions with ethyl nitroacetate ((Z) > (E)), ethyl 3-nitrobenzoylacetate ((E) > (Z)), ethyl 2-fluorobenzoylacetate ((E) > (Z)), and tetronic acid ((Z) > (E)) gave a mixture of (E)- and (Z)-isomers, whereas those of benzoylnitromethane (Z), 5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one (E), 4-hydroxy-6-methyl-2-pyrone (E), 4-hydroxycoumarin (E), 6-chloro-4-hydroxycoumarin (E), and 6-bromo-4-hydroxycoumarin (E) afforded only single stereoisomers. The reactions with 4-hydroxy-1-methyl-2(1H)-quinolone, 2-hydroxy-1,4-naphthoquinone and homophthalic anhydride gave only single stereoisomers whose stereochemistry is uncertain. It appears that geometrically more rigid cyclic 1,3-dicarbonyl compounds give better yields of dithiazol-5-ylidenes than the corresponding acyclic compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.