2,3-bis(methoxycarbonyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-benzothiopyran-4-thione | 135192-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis(methoxycarbonyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-benzothiopyran-4-thione
• CAS: 135192-62-0
• 化学式: C₁₅H₁₆O₅S₂
• 分子量: 340.421
• InChiKey: WGKMIQUZWRNOFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  1,3-dimethyl-2-(4,4-dimethyl-2,6-dithioxocyclohexylidene)imidazolidine 、 丁炔二酸二甲酯 以 甲苯 为溶剂， 以18%的产率得到2,3-bis(methoxycarbonyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-benzothiopyran-4-thione
  参考文献：
  名称：

  Addition of twisted 1,1-bis(thioacyl)-2,2-diaminoethylenes to dimethyl acetylenedicarboxylate. 2. Structure determination of two isomeric spiro adducts by x-ray crystallography and of a rearrangement product by the 2D INADEQUATE technique

  摘要：

  1,3-Dialkyl-2-(4,4-dimethyl-2,6-dithioxocyclohexylidene)imidazolidines (twisted push-pull ethylenes) react smoothly with dimethyl acetylenedicarboxylate (DMAD) but require at least 3 equiv of DMAD for complete consumption. Chromatography of the complex reaction mixture gave two isomeric 1:2 adducts, shown by X-ray crystallography to be (E)- and (Z)-[1,2-bis(methoxycarbonyl)vinyl]thio-susbstituted thiopyran-4-spiro-2'-imidazolidines. Treatment of the spior compounds with dilute nonaqueous acid led to isomers in which the imidazolidine ring had opened, and acid hydrolysis gave a thiopyrone and its enol tautomer. Continued chromatography of the original reaction mixture gave three new compounds, a thiopyran-4-thione, a tetrakis-(methoxycarbonyl)-1,4-dithiaphenalene, and a precursor to this with the same ring system. The formation of these compounds requires migration of a sulfur atom from the cyclohexene ring to the annelated thiopyran ring, and a possible mechanism is discussed. The dithiaphenalene structure was firmly established by the 2D INADEQUATE technique.

  DOI：

  10.1021/jo00016a021