Ethyl 1-[(2-ethoxy-2-oxoethyl)-methylcarbamoyl]piperidine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Ethyl 1-[(2-ethoxy-2-oxoethyl)-methylcarbamoyl]piperidine-2-carboxylate
• 化学式: C₁₄H₂₄N₂O₅
• 分子量: 300.355
• InChiKey: PITQWIFDMUMOOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(Mesyloxy)-2-carbethoxy-N-methylacetamide 、 2-哌啶甲酸乙酯 以 二氯甲烷 为溶剂， 以84%的产率得到Ethyl 1-[(2-ethoxy-2-oxoethyl)-methylcarbamoyl]piperidine-2-carboxylate
  参考文献：
  名称：

  Origins of Regioselectivity in the Reactions of .alpha.-Lactams with Nucleophiles

  摘要：

  Regioselectivity in the reaction of alpha-lactams with nucleophiles results from two competing steps. Nucleophilic addition to the carbonyl group of the alpha-lactam, which yields rearranged, acyl-substituted products, is dependent on the nucleophilicity and the concentration of the nucleophile. Ring opening of the alpha-lactam to an ion pair intermediate, which gives nucleophile incorporation at C-2, is dependent on electronic effects of substituents at C-2. Groups which can stabilize positive charge at C-2 speed up ion pair formation, whereas electron-withdrawing groups slow the ring opening and give more carbonyl addition product. These factors are used to control the regioselectivity and produce a series of unsymmetric urea peptide mimetics in high yields and with complete regiochemical control.

  DOI：

  10.1021/jo00118a032

文献信息

• Origins of Regioselectivity in the Reactions of .alpha.-Lactams with Nucleophiles
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00118a032

  日期：1995.6

  Regioselectivity in the reaction of alpha-lactams with nucleophiles results from two competing steps. Nucleophilic addition to the carbonyl group of the alpha-lactam, which yields rearranged, acyl-substituted products, is dependent on the nucleophilicity and the concentration of the nucleophile. Ring opening of the alpha-lactam to an ion pair intermediate, which gives nucleophile incorporation at C-2, is dependent on electronic effects of substituents at C-2. Groups which can stabilize positive charge at C-2 speed up ion pair formation, whereas electron-withdrawing groups slow the ring opening and give more carbonyl addition product. These factors are used to control the regioselectivity and produce a series of unsymmetric urea peptide mimetics in high yields and with complete regiochemical control.