2,2-dichloro-N-(4-ethoxyphenyl)-3-oxobutanamide | 1477491-93-2

• 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: 2,2-dichloro-N-(4-ethoxyphenyl)-3-oxobutanamide
• CAS: 1477491-93-2
• 化学式: C₁₂H₁₃Cl₂NO₃
• 分子量: 290.146
• InChiKey: YXGXNQPESISTBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对乙氧基-N-乙酰乙酰苯胺 在 (二氯碘)-苯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以70%的产率得到2,2-dichloro-N-(4-ethoxyphenyl)-3-oxobutanamide
  参考文献：
  名称：

  Iodobenzene Dichloride Mediated Sequential C–Cl Bond Formation: A Safe, Convenient and Efficient Method for the Direct α,α-Dichlorination of β-Dicarbonyl Compounds

  摘要：

  Various -keto esters, 1,3-diketones, and -oxo amides are directly converted into their corresponding ,-dichloro--keto esters, 2,2-dichloro-1,3-diketones, and ,-dichloro--oxo amides, respectively, in moderate to high yields, using iodobenzene dichloride in dichloromethane in the presence of 4 angstrom molecular sieves at room temperature. This process is postulated to proceed via the iodobenzene dichloride mediated sequential oxidative -chlorination of the -dicarbonyl substrates.

  DOI：

  10.1055/s-0034-1379973

文献信息

• Palladium(II)-Catalyzed Sequential C−Cl Bond Formation: A Novel and Efficient Method for Direct α,α-Dichlorination of β-Dicarbonyl Compounds
  作者：Weibing Liu、Liquan Tan、Peng Zhou、Cui Chen、Qing Zhang

  DOI：10.1055/s-0033-1338515

  日期：——

  A simple and concise procedure for the synthesis of 2,2-dichloro-3-oxo-N-phenylbutanamides, via palladium-catalyzed C(sp(3))-H dichlorination of 3-oxo-N-phenylbutanamides, is described. The protocol provides a direct route to ,-dichlorinated products starting from -dicarbonyl compounds. A plausible mechanism for this transformation involving two consecutive chlorination steps is described.