ethyl 2-ethylidene-4-methyl-3-oxopentanoate | 1373511-54-6

• 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: ethyl 2-ethylidene-4-methyl-3-oxopentanoate
• CAS: 1373511-54-6
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: WOYPWJGTKPVFGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-环丙基-3-羰基-丙酸乙酯 在 1,10-菲罗啉 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 ethyl 2-ethylidene-4-methyl-3-oxopentanoate 、 ethyl 2-(cyclopropanecarbonyl)-3-(4-methylphenylsulfonamido)butanoate
  参考文献：
  名称：

  Copper(II) Triflate Catalyzed Amination and Aziridination of 2-Alkyl Substituted 1,3-Dicarbonyl Compounds

  摘要：

  A method to prepare alpha-acyl-beta-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)(2) + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI=NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C-H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the beta-aminatecl adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2-3 equiv was discovered to result in preferential formal aziridination of the C-C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.

  DOI：

  10.1021/ja301415k