diethyl 2-(1-(4-chlorophenyl)-2-cyano-3-(4-methoxyphenylamino)-3-oxopropyl)malonate | 1248705-75-0

• 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: diethyl 2-(1-(4-chlorophenyl)-2-cyano-3-(4-methoxyphenylamino)-3-oxopropyl)malonate
• 英文别名: Diethyl 2-[1-(4-chlorophenyl)-2-cyano-3-(4-methoxyanilino)-3-oxopropyl]propanedioate
• CAS: 1248705-75-0
• 化学式: C₂₄H₂₅ClN₂O₆
• 分子量: 472.925
• InChiKey: MDVKIMYKXNXKCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2-(1-(4-chlorophenyl)-2-cyano-3-(4-methoxyphenylamino)-3-oxopropyl)malonate 在 亚碘酰苯 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以65%的产率得到ethyl 3-(4-chlorophenyl)-2-cyano-2-((4-methoxyphenyl)carbamoyl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Carbamoyl-2-cyanocyclopropanecarboxylates by Tandem Oxidative Cyclization and Neighboring Group-Assisted Decarboxylation

  摘要：

  In this paper. we report a facile synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates through a tandem iodosobenzene/tetrabutylammonium iodide-induced oxidative cyclization and a subsequent neighboring group-assisted decarboxylation of the Michael adducts of 2-eyanoacetamides with alpha,beta-unsaturated malonates. This method affords the desired highly functionalized cyclopropanes in moderate to good yields and with excellent chastereo selectivities. In addition, the reaction proceeds smoothly under mild conditions and with good functional group tolerance

  DOI：

  10.1021/jo1014245
• 作为产物：
  描述：

  2-氰基-N-(4-甲氧基苯基)乙酰胺 、 [(4-氯苯基)亚甲基]丙二酸二乙酯 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 diethyl 2-(1-(4-chlorophenyl)-2-cyano-3-(4-methoxyphenylamino)-3-oxopropyl)malonate
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Carbamoyl-2-cyanocyclopropanecarboxylates by Tandem Oxidative Cyclization and Neighboring Group-Assisted Decarboxylation

  摘要：

  In this paper. we report a facile synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates through a tandem iodosobenzene/tetrabutylammonium iodide-induced oxidative cyclization and a subsequent neighboring group-assisted decarboxylation of the Michael adducts of 2-eyanoacetamides with alpha,beta-unsaturated malonates. This method affords the desired highly functionalized cyclopropanes in moderate to good yields and with excellent chastereo selectivities. In addition, the reaction proceeds smoothly under mild conditions and with good functional group tolerance

  DOI：

  10.1021/jo1014245

文献信息

• Stereoselective Synthesis of 2-Carbamoyl-2-cyanocyclopropanecarboxylates by Tandem Oxidative Cyclization and Neighboring Group-Assisted Decarboxylation
  作者：Hua Wang、Renhua Fan

  DOI：10.1021/jo1014245

  日期：2010.10.15

  In this paper. we report a facile synthesis of 2-carbamoyl-2-cyanocyclopropanecarboxylates through a tandem iodosobenzene/tetrabutylammonium iodide-induced oxidative cyclization and a subsequent neighboring group-assisted decarboxylation of the Michael adducts of 2-eyanoacetamides with alpha,beta-unsaturated malonates. This method affords the desired highly functionalized cyclopropanes in moderate to good yields and with excellent chastereo selectivities. In addition, the reaction proceeds smoothly under mild conditions and with good functional group tolerance