Ethyl 2-[methyl(methylcarbamoyl)amino]acetate | 104892-33-3

• 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 2-[methyl(methylcarbamoyl)amino]acetate
• CAS: 104892-33-3
• 化学式: C₇H₁₄N₂O₃
• 分子量: 174.2
• InChiKey: IFQGAJGNUYYASR-UHFFFAOYSA-N

物化性质

• 熔点：
  62-65 °C
• 沸点：
  329.0±25.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-[methyl(methylcarbamoyl)amino]acetate 生成 1,3-二甲基海因
  参考文献：
  名称：

  Atay, Ergun; Blagoeva, Iva B.; Kirby, Anthony J., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 10, p. 2289 - 2297

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(Mesyloxy)-2-carbethoxy-N-methylacetamide 、 甲胺 以 二氯甲烷 为溶剂， 以80%的产率得到Ethyl 2-[methyl(methylcarbamoyl)amino]acetate
  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

• NH-Acidities of Some Sterically Hindered Ureas†
  作者：Ivan G. Pojarlieff、Iva B. Blagoeva、Bozhana P. Mikhova、Ergun Atay、Anthony J. Kirby

  DOI：10.1039/a608619e

  日期：——

  Introduction of an N-methyl group in to ethyl N-methylhydantoate causes a fourfold decrease in the rate of base-catalysed exchange of the N-H proton; a second methyl group restores the rate to close to that of the N-unsubstituted hydantoate; the latter effect is observed for N-phenylhydantoates.

  将 N-甲基引入 N-甲基海因酸乙酯会导致 NH 质子的碱催化交换速率降低四倍；第二个甲基使速率恢复到接近 N-未取代的乙内酰脲的速率；对于 N-苯海因酸盐观察到后一种效应。
• Kavalek, Jaromir; Machacek, Vladimir; Svobodova, Gabriela, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 2, p. 375 - 390
  作者：Kavalek, Jaromir、Machacek, Vladimir、Svobodova, Gabriela、Sterba, Vojeslav

  DOI：——

  日期：——
• KAVALEK, J.;MACHACEK, V.;SVOBODOVA, G.;STERBA, V., COLLECT. CZECHOSL. CHEM. COMMUN., 1986, 51, N 2, 375-390
  作者：KAVALEK, J.、MACHACEK, V.、SVOBODOVA, G.、STERBA, V.

  DOI：——

  日期：——
• 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.
• Atay, Ergun; Blagoeva, Iva B.; Kirby, Anthony J., Journal of the Chemical Society. Perkin Transactions 2 (2001), 1998, # 10, p. 2289 - 2297
  作者：Atay, Ergun、Blagoeva, Iva B.、Kirby, Anthony J.、Pojarlieff, Ivan G.

  DOI：——

  日期：——