1-<5,6-dihydro-2-methyl-6-N-(2'-oxo-2',3',4',5'-tetrahydropyrrolo)-1,4-oxathiin-3-yl>ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环己烯
• 英文名称: 1-<5,6-dihydro-2-methyl-6-N-(2'-oxo-2',3',4',5'-tetrahydropyrrolo)-1,4-oxathiin-3-yl>ethanone
• 英文别名: 1-(5-Acetyl-6-methyl-2,3-dihydro-1,4-oxathiin-2-yl)pyrrolidin-2-one
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: NJUHXTFIHLYDEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(三甲基硅氧基)-3-戊烯-2-酮 在 吡啶 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 52.0h， 生成 1-<5,6-dihydro-2-methyl-6-N-(2'-oxo-2',3',4',5'-tetrahydropyrrolo)-1,4-oxathiin-3-yl>ethanone
  参考文献：
  名称：

  Phthalimidesulfenyl Chloride. 9. A Simple Access to .alpha.,.alpha.'-Dioxothiones, a New Class of Bis-heterodienes. Synthesis of 1,4-Oxathiin Systems

  摘要：

  alpha,alpha'-Dioxothiophthalimides 4a and 4b react with pyridine to generate the alpha,alpha'-dioxothiones 5a and 5b which undergo chemo- and regiospecific inverse electron demand Diels-Alder reactions With electron-rich alkenes to give 1,4-oxathiin heterocyclic systems. Enol ethers, silyl enol ethers, vinyl sulfides, vinyl amides, substituted styrenes, and electron rich alkynes and allenes can be fruitfully employed as dienophiles. Among the vinyl ethers tested tri-O-benzylglucal was successfully used as a dienophile. Ab initio molecular orbital calculations performed on thiones 5a and 5b as well as on a selected enol ether are consistent with the experimental results. When thione 5a was generated in the presence of 2,3-dimethyl-2-butene (31) and -(beta)-pinene (33) a selective ''thiophlic ene reaction'' was observed leading to the formation of sulfides 32 and 34. Thione 5b reacted similarly with 33 to generate the sulfide 35. Additionally a competition between the dienic versus dienophilic behavior of alpha,alpha'-dioxothiones 5a and 5b was observed in reactions with 2,3-dimethoxy-1,3-butadiene (45) and 2-methoxyfuran (50). A preliminary screening of the reactivity of 1,4-oxathiins 7c and 8b, used as model substrates, is also outlined.

  DOI：

  10.1021/jo00125a030

文献信息

• Phthalimidesulfenyl Chloride. 9. A Simple Access to .alpha.,.alpha.'-Dioxothiones, a New Class of Bis-heterodienes. Synthesis of 1,4-Oxathiin Systems
  作者：G. Capozzi、R. W. Franck、M. Mattioli、S. Menichetti、C. Nativi、G. Valle

  DOI：10.1021/jo00125a030

  日期：1995.10

  alpha,alpha'-Dioxothiophthalimides 4a and 4b react with pyridine to generate the alpha,alpha'-dioxothiones 5a and 5b which undergo chemo- and regiospecific inverse electron demand Diels-Alder reactions With electron-rich alkenes to give 1,4-oxathiin heterocyclic systems. Enol ethers, silyl enol ethers, vinyl sulfides, vinyl amides, substituted styrenes, and electron rich alkynes and allenes can be fruitfully employed as dienophiles. Among the vinyl ethers tested tri-O-benzylglucal was successfully used as a dienophile. Ab initio molecular orbital calculations performed on thiones 5a and 5b as well as on a selected enol ether are consistent with the experimental results. When thione 5a was generated in the presence of 2,3-dimethyl-2-butene (31) and -(beta)-pinene (33) a selective ''thiophlic ene reaction'' was observed leading to the formation of sulfides 32 and 34. Thione 5b reacted similarly with 33 to generate the sulfide 35. Additionally a competition between the dienic versus dienophilic behavior of alpha,alpha'-dioxothiones 5a and 5b was observed in reactions with 2,3-dimethoxy-1,3-butadiene (45) and 2-methoxyfuran (50). A preliminary screening of the reactivity of 1,4-oxathiins 7c and 8b, used as model substrates, is also outlined.