methyl 2-(1'-acetoxyethyl)pent-4-enoate | 139313-39-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-(1'-acetoxyethyl)pent-4-enoate
• 英文别名: methyl 2-(1-acetyloxyethyl)pent-4-enoate
• CAS: 139313-39-6
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: JRRJCAROHLYTHK-UHFFFAOYSA-N

物化性质

• 沸点：
  164.2±20.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 2-(1-hydroxyethyl)pent-4-enoate 在 乙酸酐 、 cobalt(II) chloride 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以72%的产率得到methyl 2-(1'-acetoxyethyl)pent-4-enoate
  参考文献：
  名称：

  Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism

  摘要：

  Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield. Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones. Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate. The beta-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting beta-acetoxy carbonyl compound is observed. A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene. A mechanism for these acylations is proposed by invoking an electron-transfer process.

  DOI：

  10.1021/jo00033a020