ethyl 3-(4-iodophenyl)-2-methyl-3-oxopropanoate | 1373511-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-(4-iodophenyl)-2-methyl-3-oxopropanoate
• 英文别名: Benzenepropanoic acid, 4-iodo-I+/--methyl-I(2)-oxo-, ethyl ester
• CAS: 1373511-21-7
• 化学式: C₁₂H₁₃IO₃
• 分子量: 332.138
• InChiKey: VJUDKFGMBBDVFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-iodophenyl)-2-methyl-3-oxopropanoate 、 [(N-tosylimino)iodo]benzene 在 1,10-菲罗啉 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以62%的产率得到ethyl 2-(4-iodobenzoyl)-1-tosylaziridine-2-carboxylate
  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
• 作为产物：
  描述：

  乙基 (4-碘苯甲酰)乙酸 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 3-(4-iodophenyl)-2-methyl-3-oxopropanoate
  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