4-(o-chlorophenyl)-2,3-diketobutyramide hydrate | 133373-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(o-chlorophenyl)-2,3-diketobutyramide hydrate
• 英文别名: 4-(2-Chlorophenyl)-2,2-dihydroxy-3-oxobutanamide；4-(2-chlorophenyl)-2,2-dihydroxy-3-oxobutanamide
• CAS: 133373-29-2
• 化学式: C₁₀H₁₀ClNO₄
• 分子量: 243.647
• InChiKey: WJXPTXOHCJEFDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(o-chlorophenyl)-2,3-diketobutyramide hydrate 在 硫酸 作用下， 反应 1.5h， 以95%的产率得到rac-3-(2-chlorophenyl)-2-hydroxypropionic acid
  参考文献：
  名称：

  Unstable 1,1,2-enetriols as (probable) intermediates in the decarboxylation of .alpha.,.beta.-diketo acids

  摘要：

  During the acid hydrolyis of (hydrated) 4-aryl-2,3-diketobutyramide 2 (aryl = phenyl, o-chlorophenyl, p-methoxyphenyl), 3-aryllactic acid (5) is formed by rapid decarboxylation of the intermediate diketo acid (3). In the decarboxylation step, a further unstable intermediate is formed. The latter manifests itself by reducing 1 mol of added iodine during the hydrolysis-decarboxylation reaction, thereby forming 3-arylpyruvic acid (6), isolated instead of 5. Thus, the oxidation of the unstable intermediate by iodine is more rapid than its ketonization. It is formulated as an 1,1,2-enetriol (4), more probable than an alpha-hydroxyketene.

  DOI：

  10.1021/jo00009a029