N-(Mesyloxy)-2-carbethoxy-N-methylacetamide | 164933-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(Mesyloxy)-2-carbethoxy-N-methylacetamide
• 英文别名: Ethyl 3-[methyl(methylsulfonyloxy)amino]-3-oxopropanoate
• CAS: 164933-11-3
• 化学式: C₇H₁₃NO₆S
• 分子量: 239.249
• InChiKey: GHRXACNQZIYSAO-UHFFFAOYSA-N

物化性质

• 沸点：
  322.8±44.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dibenzylhydrazine hydrochloride 、 N-(Mesyloxy)-2-carbethoxy-N-methylacetamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以67%的产率得到Ethyl 2-[[benzyl-(benzylamino)carbamoyl]-methylamino]acetate
  参考文献：
  名称：

  The Reactions of Hydrazines with α-Lactams. Regiochemistry of Hydrazine Addition and Subsequent Ring Closure to N-Aminohydantoins or 1,2,4-Triazine-3,6-diones

  摘要：

  DOI：

  10.1021/jo981650c
• 作为产物：
  描述：

  甲基磺酰氯 、 N-hydroxy-N-methyl-2-carbetoxyethanamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到N-(Mesyloxy)-2-carbethoxy-N-methylacetamide
  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

• Reaction of Hydrazines with .alpha.-Lactams for the Preparation of 1,2,4-Triazine-3,6-diones and Aza-Urea Peptide Mimetics
  作者：Robert V. Hoffman、Naresh K. Nayyar

  DOI：10.1021/jo00123a048

  日期：1995.9
• Improved Methodology for the Generation and Trapping of α-Lactams by Weak Nucleophiles
  作者：Robert V. Hoffman、Madhava M. Reddy、Francisco Cervantes-Lee

  DOI：10.1021/jo991732g

  日期：2000.4.1
• The Reactions of Hydrazines with α-Lactams. Regiochemistry of Hydrazine Addition and Subsequent Ring Closure to <i>N</i>-Aminohydantoins or 1,2,4-Triazine-3,6-diones
  作者：Robert V. Hoffman、Madhava M. Reddy、Curtis M. Klumas、Francisco Cervantes-Lee

  DOI：10.1021/jo981650c

  日期：1998.11.1
• 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.