1-丁酮,3-(乙酰氧基)-2-甲基-1-苯基- | 139313-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-丁酮,3-(乙酰氧基)-2-甲基-1-苯基-
• 英文名称: 3-acetoxy-2-methylbutyrophenone
• 英文别名: (3-Methyl-4-oxo-4-phenylbutan-2-yl) acetate
• CAS: 139313-41-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: NNNJBQXTJKZRQK-UHFFFAOYSA-N

物化性质

• 沸点：
  323.7±25.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-phenyl-2-methyl-3-hydroxybutan-1-one 在 4-二甲氨基吡啶 、 乙酸酐 、 三乙胺 作用下， 以59%的产率得到1-丁酮,3-(乙酰氧基)-2-甲基-1-苯基-
  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

文献信息

• Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1021/jo00033a020

  日期：1992.3

  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.