methyl 4-(2-ethyl-5-oxo-pyrrolidin-2-yl)benzoate | 1610701-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: methyl 4-(2-ethyl-5-oxo-pyrrolidin-2-yl)benzoate
• CAS: 1610701-54-6
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: WUMFCBCIAIGUPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  methyl 4-(1-ethyl-3-methoxycarbonyl-1-nitropropyl)benzoate 在 sodium tetrahydroborate 、 nickel chloride hexahydrate 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以85%的产率得到methyl 4-(2-ethyl-5-oxo-pyrrolidin-2-yl)benzoate
  参考文献：
  名称：

  Synthesis of 5-alkyl-5-aryl-γ-lactams from 1-aryl-substituted nitroalkanes and methyl acrylate via Michael addition and reductive lactamization

  摘要：

  A general method for accessing 5-alkyl-5-aryl-gamma-lactams has been developed using readily available aryl bromides, nitroalkanes, and methyl acrylate as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the DBU-mediated Michael addition with methyl acrylate at room temperature to afford the methyl 4-aryl-4-nitroalkanoates. The latter were then subjected to the nitro reduction using NaBH4-NiCl2 center dot 6H(2)O in MeOH at 0 degrees C to furnish, after treatment with aqueous K2CO3 at room temperature, the 5-alkyl-5-aryl-gamma-lactams in good to excellent overall yields. Selected examples of N-alkylation of the gamma-lactams were also illustrated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.074