Methyl 2-(propionyloxy)-4-oxohexanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Methyl 2-(propionyloxy)-4-oxohexanoate
• 英文别名: Methyl 2-propionoxy-4-oxohexanoate；Methyl 4-oxo-2-propanoyloxyhexanoate
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: LCHMSNSBOPKKEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙醛 、 丙烯酸甲酯（MA） 在 Schiff's base ligand 1a 氧气 作用下， 以 乙腈 为溶剂， 以14%的产率得到Methyl 2-hydroxy-4-oxohexanoate
  参考文献：
  名称：

  钴（II）催化烯烃与脂肪醛和分子氧的反应：范围和机理

  摘要：

  可以使用衍生自芳族醛和胺或α-氨基酯的席夫碱制备各种钴（II）配合物。这些络合物是脂肪族醛与各种烯烃之间反应的通用催化剂。反应的结果受烯烃的电子性质控制，因为缺电子的烯烃经历醛的氧化加成反应，然后引入双氧生成2-羟基（酰氧基）-4-氧酸酯或腈，而未活化或富电子的烯烃则提供了相应的环氧化物。这些反应是通过自由基途径进行的，并提出了一种常见的酰基钴中间体，用于形成4和环氧化物7。

  DOI：

  10.1016/s0040-4020(01)87194-5

文献信息

• Cobalt(II)-catalyzed reaction of aldehydes with acetic anhydride under an oxygen atmosphere: scope and mechanism
  作者：Beena Bhatia、T. Punniyamurthy、Javed Iqbal

  DOI：10.1021/jo00072a041

  日期：1993.9

  The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium. Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals. On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene. Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the corresponding anhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions. A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes. Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurrence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.
• Cobalt(II)-Catalyzed Reaction of Enolizable Aldehydes with Alkenes in the Presence of Dioxygen: The Role of Acyl Radical
  作者：T. Punniyamurthy、Beena Bhatia、Javed Iqbal

  DOI：10.1021/jo00083a029

  日期：1994.2

  Complex [bis(salicylidene-N-phenethyl)] cobalt(II) (1) catalyzes the reaction of enolizable aliphatic aldehydes and dioxygen with an electron-deficient alkene to afford the adducts 4 and 5, whereas the reaction with unactivated alkenes leads to the corresponding epoxides 6. These reactions are proposed to proceed via a common pathway involving acyl radicals.