ethyl 2-(N-phthalimidyloxy)-2-ethyl-3-oxobutanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 2-(N-phthalimidyloxy)-2-ethyl-3-oxobutanoate
• 英文别名: Ethyl 2-(1,3-dioxoisoindol-2-yl)oxy-2-ethyl-3-oxobutanoate；ethyl 2-(1,3-dioxoisoindol-2-yl)oxy-2-ethyl-3-oxobutanoate
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: ZCQSMQWHJGWDIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 2-乙基乙酰乙酸乙酯 在 cobalt(II) diacetate tetrahydrate 、 potassium permanganate 作用下， 以 溶剂黄146 为溶剂， 反应 0.19h， 以94%的产率得到ethyl 2-(N-phthalimidyloxy)-2-ethyl-3-oxobutanoate
  参考文献：
  名称：

  1,3-二羰基化合物的氧化CO交叉偶联及其与N-取代的异羟肟酸和N-羟基酰亚胺的异醛类似物

  摘要：

  AbstractThe oxidative CO cross‐coupling of 1,3‐dicarbonyl compounds and their heteroanalogues, 2‐substituted malononitriles and cyanoacetic esters, with N‐substituted hydroxamic acids and N‐hydroxyimides was realized. The best results were obtained with the use of manganese(III) acetate [Mn(OAc)3] or the cobalt(II) acetate catalyst [Co(OAc)2cat.]/potassium permanganate [KMnO4] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30–94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N‐substituted hydroxamic acids and N‐hydroxyimides.magnified image

  DOI：

  10.1002/adsc.201300341

文献信息

• Oxidative CO Cross-Coupling of 1,3-Dicarbonyl Compounds and Their Heteroanalogues with<i>N</i>-Substituted Hydroxamic Acids and<i>N</i>-Hydroxyimides
  作者：Alexander O. Terent'ev、Igor B. Krylov、Vladimir P. Timofeev、Zoya A. Starikova、Valentina M. Merkulova、Alexey I. Ilovaisky、Gennady I. Nikishin

  DOI：10.1002/adsc.201300341

  日期：2013.8.12

  AbstractThe oxidative CO cross‐coupling of 1,3‐dicarbonyl compounds and their heteroanalogues, 2‐substituted malononitriles and cyanoacetic esters, with N‐substituted hydroxamic acids and N‐hydroxyimides was realized. The best results were obtained with the use of manganese(III) acetate [Mn(OAc)3] or the cobalt(II) acetate catalyst [Co(OAc)2cat.]/potassium permanganate [KMnO4] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30–94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N‐substituted hydroxamic acids and N‐hydroxyimides.magnified image