2-oxo-2H-1-benzothiopyran-3-carbonitrile | 25863-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 2-oxo-2H-1-benzothiopyran-3-carbonitrile
• 英文别名: 3-Cyan-1-thio-cumarin；2-oxo-2H-thiochromene-3-carbonitrile；2-Oxothiochromene-3-carbonitrile
• CAS: 25863-65-4
• 化学式: C₁₀H₅NOS
• 分子量: 187.222
• InChiKey: LTHJNIBQLTZXTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-2H-1-benzothiopyran-3-carbonitrile 、 2,3-二甲基-2-丁烯 以 乙腈 为溶剂， 反应 30.0h， 以64%的产率得到cis-3-oxo-1,1,2,2-tetramethyl-1,2-dihydro-3H,8bH-cyclobuta[c]benzothiopyran-2a-carbonitrile
  参考文献：
  名称：

  摘要：

  Both (intermolecular) photocycloadditions of 2H-1-benzopyran- and 2H-1-benzothiopyran-3-carbanitriles to 2,3-dimethylbut-2-ene and 2-methylbut-1-en-3-yne, and (intramolecular) photoisomerization of 4-(alkenyl)benzopyran-3-carbooitriles were investigated. In contrast to 2H-1-benzopyran-3-carbonitrile (1), its thia analog 4 reacts with 2,3-dimethylbut-2-ene selectively, to afford only cyclobuta derivative 2 In the presence of 2-methylbut-1-en-3-yne, both 1 and 4 behave alike to afford the all-cis-cyclobuta diastereoisomers, 15 and 8, respectively, as main products, as well as minor amounts of cyclobutenes 17 and 10, respectively, which result from the addition of the terminal C-atom of the acetylenic bond to C(3) of the heterocycle. 4-Methyl-2H-1-benzopyran-3-carbonitrile (5) does not undergo photoaddition to the alkene or the alkenyne mentioned above, whereas the corresponding intramolecular [2 + 2] photocycloaddition of 4-(pent-4-enyl)benzopyran-3-carbonitrile (6b) to tetracycle 20 proceeds quantitatively.

  DOI：

  10.1002/1522-2675(20000607)83:6<1168::aid-hlca1168>3.0.co;2-y