4,5-dihydrocyclopenta[b]thiophen-6-one oxime | 14600-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 4,5-dihydrocyclopenta[b]thiophen-6-one oxime
• 英文别名: 6-Oximino-4,5-dihydro-6H-cyclopentathiophen；N-(4,5-dihydrocyclopenta[b]thiophen-6-ylidene)hydroxylamine
• CAS: 14600-24-9
• 化学式: C₇H₇NOS
• 分子量: 153.205
• InChiKey: GOLWSRVBSVLITK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dihydrocyclopenta[b]thiophen-6-one oxime 在 PPA 作用下， 生成 5,6-二氢噻吩并[2,3-c]吡啶-7(4H)-酮
  参考文献：
  名称：

  Aparajithan,K. et al., Journal of Heterocyclic Chemistry, 1966, vol. 3, p. 466 - 469

  摘要：

  DOI：

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.