2-acetoxy-2-acetylamino-propionic acid ethyl ester | 62183-00-0

• 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: 2-acetoxy-2-acetylamino-propionic acid ethyl ester
• 英文别名: Ethyl 2-acetamido-2-acetyloxypropanoate
• CAS: 62183-00-0
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: XAEBLIZAVMFLFR-UHFFFAOYSA-N

物化性质

• 沸点：
  361.5±27.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-acetoxy-2-acetylamino-propionic acid ethyl ester 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-acetamidoacrylate
  参考文献：
  名称：

  Syntheses of amino acids and related compounds. 19. New versatile syntheses of 2-substituted-2-amino acid and 2,3-dehydro-2-amino acid derivatives

  摘要：

  DOI：

  10.1021/jo01317a017
• 作为产物：
  描述：

  diethyl α-acetamido, α-methylmalonate 在 氢氧化钾 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 2-acetoxy-2-acetylamino-propionic acid ethyl ester
  参考文献：
  名称：

  2-乙酰氧基-2-氨基酸和3-乙酰氧基-3-氨基酸衍生物的电化学合成。

  摘要：

  DOI：

  10.1021/jo00434a015

文献信息

• Synthesis of .alpha.-substituted .alpha.-amino acids via cationic intermediates
  作者：Eric C. Roos、M. Carmen Lopez、Michael A. Brook、Henk Hiemstra、W. Nico Speckamp、Bernard Kaptein、Johan Kamphuis、Hans E. Schoemaker

  DOI：10.1021/jo00064a011

  日期：1993.6

  A novel synthetic approach to racemic alpha-substituted alpha-amino acids is described. The key intermediates of this methodology are highly electrophilic iminium ions, bearing carbonyl substituents at both the iminium carbon and nitrogen atom. The preparation of precursors 8, 10a-c, and 12 includes electrochemical oxidation techniques according to literature procedures. When an alpha-methyl precursor (8 or 10a) was used, reactions with allylsilanes and silyl enol ethers led to the desired products, but elimination to dehydroalanine derivatives appeared to be an important side reaction. A major improvement in the yields of the desired products could be effected by using longer reaction times. In this way, efficient syntheses of protected alpha-methyl-alpha-amino acids could be developed. The elimination process appeared to be a more serious problem in the alpha-benzyl (10b) and alpha-allyl (10c) cases. On the other hand, the alpha-phenyl precursor 12 appeared to be highly useful, because the elimination is impossible in this case. High yields of alpha-phenyl-alpha-amino acid derivatives were obtained upon reaction of 12 with silicon-activated pi-nucleophiles. Deprotection led to various types of free alpha-substituted alpha-amino acids.
• Syntheses of amino acids and related compounds. 22. Efficient synthesis of 3-substituted aspartic acids
  作者：Yasuhiko Ozaki、Tameo Iwasaki、Muneji Miyoshi、Kazuo Matsumoto

  DOI：10.1021/jo01324a029

  日期：1979.5