methyl 6-chloro-5-{4-[4-(dimethylamino)phenylazo]phenylamino}cyclopenta[d][1,2,3]dithiazol-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: methyl 6-chloro-5-{4-[4-(dimethylamino)phenylazo]phenylamino}cyclopenta[d][1,2,3]dithiazol-4-carboxylate
• 英文别名: Methyl 6-chloro-5-[4-[[4-(dimethylamino)phenyl]diazenyl]anilino]cyclopenta[d]dithiazole-4-carboxylate
• 化学式: C₂₁H₁₈ClN₅O₂S₂
• 分子量: 471.991
• InChiKey: QGEUZNMCLMCOCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-methoxycarbonylcyclopentanone oxime 在 二氯化二硫 、 三异丁基胺 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 methyl 6-chloro-5-{4-[4-(dimethylamino)phenylazo]phenylamino}cyclopenta[d][1,2,3]dithiazol-4-carboxylate
  参考文献：
  名称：

  From Cyclopentanone Oximes to Bis[1,2,3]dithiazolo-s-indacenes, Cyclopenta[c][1,2]thiazine, Pentathiepino-, Tetrathiino-, and Thienocyclopenta[1,2,3]dithiazoles as a Rich Source of New Materials

  摘要：

  The 1,5- and 1,7-s-hydrindacenedione dioximes reacted with S2Cl2 and (Bu3N)-Bu-i to give the first examples of bis[1,2,3]dithiazolo-s-indacenes; one of them was a near-infrared dye. In contrast, the silylated bicyclo[3.3.0]octan-2,6-dione dioxime reacted with S2Cl2 and Et3N to give a bicyclic 4-cyanoethylcyclopenta[1,2,3]dithiazole or, after addition of Li2S, a tricyclic 4-cyanoethyl-5,6-pentathiepinocyclopenta[1,2,3]dithiazole, also obtained from 2-cyanoethylcyclopentanone oxime, S2Cl2, and Hunig's base. In related reactions, 2-oxocyclopentylpropionate oxime gave the expected cyclopenta[1,2,3]dithiazole, in addition to an unexpected cyclopenta[c] [1,2]thiazine that showed a reversible reduction wave in its CV at -0.95 V. Ethyl 2-oxocyclopentanecarboxylate oxime reacted with S2Cl2, Hunig's base, and Li2S to give a 5,6-tetrathiinocyclopenta[1,2,3]dithiazole derivative. Cyclopentathiophen-4-one oximes reacted with S2Cl2 and (Bu3N)-Bu-i to give thienocyclopenta[1,2,3]-dithiazoles that showed UV-vis spectral bands that depended on the positions of the ring fusion.

  DOI：

  10.1021/jo0514117

文献信息

• From Cyclopentanone Oximes to Bis[1,2,3]dithiazolo-<i>s</i>-indacenes, Cyclopenta[<i>c</i>][1,2]thiazine, Pentathiepino-, Tetrathiino-, and Thienocyclopenta[1,2,3]dithiazoles as a Rich Source of New Materials
  作者：Sonia Macho、Daniel Miguel、Teresa Gómez、Teresa Rodríguez、Tomás Torroba

  DOI：10.1021/jo0514117

  日期：2005.11.1

  The 1,5- and 1,7-s-hydrindacenedione dioximes reacted with S2Cl2 and (Bu3N)-Bu-i to give the first examples of bis[1,2,3]dithiazolo-s-indacenes; one of them was a near-infrared dye. In contrast, the silylated bicyclo[3.3.0]octan-2,6-dione dioxime reacted with S2Cl2 and Et3N to give a bicyclic 4-cyanoethylcyclopenta[1,2,3]dithiazole or, after addition of Li2S, a tricyclic 4-cyanoethyl-5,6-pentathiepinocyclopenta[1,2,3]dithiazole, also obtained from 2-cyanoethylcyclopentanone oxime, S2Cl2, and Hunig's base. In related reactions, 2-oxocyclopentylpropionate oxime gave the expected cyclopenta[1,2,3]dithiazole, in addition to an unexpected cyclopenta[c] [1,2]thiazine that showed a reversible reduction wave in its CV at -0.95 V. Ethyl 2-oxocyclopentanecarboxylate oxime reacted with S2Cl2, Hunig's base, and Li2S to give a 5,6-tetrathiinocyclopenta[1,2,3]dithiazole derivative. Cyclopentathiophen-4-one oximes reacted with S2Cl2 and (Bu3N)-Bu-i to give thienocyclopenta[1,2,3]-dithiazoles that showed UV-vis spectral bands that depended on the positions of the ring fusion.