2-(acetyloxymethylene)propanedial | 1073795-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(acetyloxymethylene)propanedial
• 英文别名: (2-Formyl-3-oxoprop-1-enyl) acetate；(2-formyl-3-oxoprop-1-enyl) acetate
• CAS: 1073795-64-8
• 化学式: C₆H₆O₄
• 分子量: 142.111
• InChiKey: FOBQNXWWFWRSOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(acetyloxymethylene)propanedial 在 四氯化钛 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Diene-Transmissive Hetero-Diels-Alder Cycloaddition Using Cross-Conjugated Dioxatrienes: A Novel Synthesis of Tetrahydropyran-Fused Aza- and Thia-heterocycles

  摘要：

  The diene-transmissive hetero-Diels-Alder methodology using cross-conjugated dioxatrienes [2-(R-methylene)propanedials] has been developed. The initial cycloaddition with electron-rich dienophiles, followed by the reactions of the resulting 1-oxadiene moiety of the monoadducts with amines and Lawesson's reagent generated 1-azadienes and 1-thiadienes. The second hetero-Diels-Alder reaction of these reactive heterodienes with dienophiles (tosyl isocyanate, diphenylketene, enones, and maleinimide) produced pyran-fused aza-and thiaheterocycles, providing a new synthetic method for these heterocycles.

  DOI：

  10.3987/com-08-s(n)55
• 作为产物：
  描述：

  三甲酰基甲烷 、 乙酸酐 在 吡啶 作用下， 生成 2-(acetyloxymethylene)propanedial
  参考文献：
  名称：

  Diene-Transmissive Hetero-Diels-Alder Cycloaddition Using Cross-Conjugated Dioxatrienes: A Novel Synthesis of Tetrahydropyran-Fused Aza- and Thia-heterocycles

  摘要：

  The diene-transmissive hetero-Diels-Alder methodology using cross-conjugated dioxatrienes [2-(R-methylene)propanedials] has been developed. The initial cycloaddition with electron-rich dienophiles, followed by the reactions of the resulting 1-oxadiene moiety of the monoadducts with amines and Lawesson's reagent generated 1-azadienes and 1-thiadienes. The second hetero-Diels-Alder reaction of these reactive heterodienes with dienophiles (tosyl isocyanate, diphenylketene, enones, and maleinimide) produced pyran-fused aza-and thiaheterocycles, providing a new synthetic method for these heterocycles.

  DOI：

  10.3987/com-08-s(n)55

文献信息

• Diene-Transmissive Hetero-Diels-Alder Cycloaddition Using Cross-Conjugated Dioxatrienes: A Novel Synthesis of Tetrahydropyran-Fused Aza- and Thia-heterocycles
  作者：Takao Saito、Satoru Kobayashi、Takashi Otani、Hideoki Iwanami、Takayuki Soda

  DOI：10.3987/com-08-s(n)55

  日期：——

  The diene-transmissive hetero-Diels-Alder methodology using cross-conjugated dioxatrienes [2-(R-methylene)propanedials] has been developed. The initial cycloaddition with electron-rich dienophiles, followed by the reactions of the resulting 1-oxadiene moiety of the monoadducts with amines and Lawesson's reagent generated 1-azadienes and 1-thiadienes. The second hetero-Diels-Alder reaction of these reactive heterodienes with dienophiles (tosyl isocyanate, diphenylketene, enones, and maleinimide) produced pyran-fused aza-and thiaheterocycles, providing a new synthetic method for these heterocycles.