5-methyl-1H-2-benzothiopyran-1-one | 681141-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异硫色烯
• 英文名称: 5-methyl-1H-2-benzothiopyran-1-one
• 英文别名: 5-Methylisothiochromen-1-one；5-methylisothiochromen-1-one
• CAS: 681141-90-2
• 化学式: C₁₀H₈OS
• 分子量: 176.239
• InChiKey: LFTXEUSCOFAJPN-UHFFFAOYSA-N

物化性质

• 沸点：
  308.8±42.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  四氯乙烯 、 5-methyl-1H-2-benzothiopyran-1-one 以 乙腈 为溶剂， 反应 12.0h， 以97%的产率得到2aα,8bα-1,1,2,2-tetrachloro-2,2a-dihydro-8-methyl-1H-cyclobuta[c][2]benzothiopyran-4-one
  参考文献：
  名称：

  Photocycloaddition of Isocoumarins and Isothiocoumarins to Alkenes

  摘要：

  On irradiation in the presence of tetrachloroethene (TCE), both isocoumarins 3 and isothiocoumarins 4 afford in high yields the cis-fused cycloadducts 8 and 9, while only the oxacycles 3 undergo photocycloaddition to 2,3-dimethylbut-2-ene (TME) to give mixtures of cis- and trans-fused products 10 and 11, respectively, in moderate yields. This higher efficiency in reacting with TCE as compared to TME for compounds 3 and 4 contrasts the behavior of simple cyclic enones, e.g., 5,5-dimethylcyclohex-2-enone (12), which is converted to bicyclooctanones about fifty times faster with TME than with TCE.

  DOI：

  10.1002/1522-2675(20010815)84:8<2373::aid-hlca2373>3.0.co;2-4
• 作为产物：
  描述：

  5-methylisochroman-1-one 在 三氟乙酸 作用下， 生成 5-methyl-1H-2-benzothiopyran-1-one
  参考文献：
  名称：

  Photocycloaddition of Isocoumarins and Isothiocoumarins to Alkenes

  摘要：

  On irradiation in the presence of tetrachloroethene (TCE), both isocoumarins 3 and isothiocoumarins 4 afford in high yields the cis-fused cycloadducts 8 and 9, while only the oxacycles 3 undergo photocycloaddition to 2,3-dimethylbut-2-ene (TME) to give mixtures of cis- and trans-fused products 10 and 11, respectively, in moderate yields. This higher efficiency in reacting with TCE as compared to TME for compounds 3 and 4 contrasts the behavior of simple cyclic enones, e.g., 5,5-dimethylcyclohex-2-enone (12), which is converted to bicyclooctanones about fifty times faster with TME than with TCE.

  DOI：

  10.1002/1522-2675(20010815)84:8<2373::aid-hlca2373>3.0.co;2-4

文献信息

• Photocycloaddition of Isocoumarins and Isothiocoumarins to Alkenes
  作者：Michael A. Kinder、Lars Meyer、Paul Margaretha

  DOI：10.1002/1522-2675(20010815)84:8<2373::aid-hlca2373>3.0.co;2-4

  日期：2001.8.15

  On irradiation in the presence of tetrachloroethene (TCE), both isocoumarins 3 and isothiocoumarins 4 afford in high yields the cis-fused cycloadducts 8 and 9, while only the oxacycles 3 undergo photocycloaddition to 2,3-dimethylbut-2-ene (TME) to give mixtures of cis- and trans-fused products 10 and 11, respectively, in moderate yields. This higher efficiency in reacting with TCE as compared to TME for compounds 3 and 4 contrasts the behavior of simple cyclic enones, e.g., 5,5-dimethylcyclohex-2-enone (12), which is converted to bicyclooctanones about fifty times faster with TME than with TCE.