2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione | 152420-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione
• 英文别名: 2-(2-hydroxy-4-oxopent-2-en-3-yl)sulfanylisoindole-1,3-dione
• CAS: 152420-82-1
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: KRORARDSXBTXDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione 在 吡啶 作用下， 以 氘代氯仿 、 氯仿 为溶剂， 反应 120.0h， 生成 2-[(E)-2-hydroxy-4-oxopent-2-en-3-yl]sulfanylprop-2-enal
  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
• 作为产物：
  描述：

  phthalimidesulfenyl chloride 、 乙酰丙酮 以 二氯甲烷 为溶剂， 生成 2-((E)-1-Acetyl-2-hydroxy-propenylsulfanyl)-isoindole-1,3-dione
  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

• A Base-Mediated Mild Sulfenylation of Indoles and Pyrrole with α-Acylthiones
  作者：Caterina Viglianisi、Enrico Marcantoni、Vanessa Carapacchi、Stefano Menichetti、Laura Marsili

  DOI：10.1002/ejoc.201402894

  日期：2014.10

  procedure for the sulfenylation of indoles and pyrroles based on an aromatic substitution with α-acylthiones used as electrophiles is described. The sulfenylating species were obtained, under very mild reaction conditions, from N-thiophthalimides, using a weak base (pyridine or triethylamine) as promoter. The overall yields obtained are comparable with those obtained by other known sulfenylation protocols

  描述了一种基于芳香取代的吲哚和吡咯磺基化的新程序，其中 α-酰基硫酮用作亲电子试剂。使用弱碱（吡啶或三乙胺）作为促进剂，在非常温和的反应条件下，从 N-硫代邻苯二甲酰亚胺获得亚磺酰化物质。获得的总产率与通过其他已知的亚磺酰化方案获得的产率相当，后者通常需要更苛刻的反应条件和/或含金属的路易斯酸作为促进剂。