ethyl (Z)-2-formamido-4-(ethoxymethylphosphinyl)but-2-enoate | 131131-80-1

• 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 (Z)-2-formamido-4-(ethoxymethylphosphinyl)but-2-enoate
• 英文别名: ethyl (Z)-4-[ethoxy(methyl)phosphoryl]-2-formamidobut-2-enoate
• CAS: 131131-80-1
• 化学式: C₁₀H₁₈NO₅P
• 分子量: 263.23
• InChiKey: VOQIBAKRQKPKFP-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(ethoxymethylphosphinyl)acetaldehyde 在 氰化钠 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 90.5h， 生成 ethyl (Z)-2-formamido-4-(ethoxymethylphosphinyl)but-2-enoate
  参考文献：
  名称：

  Enantioselective synthesis of both enantiomers of phosphinothricin via asymmetric hydrogenation of .alpha.-acylamido acrylates

  摘要：

  Both enantiomers of phosphinothricin (1), a naturally occuring amino acid that contains the unique methylphosphinate moiety, were prepared by asymmetric hydrogenation of alpha-acylamido acrylate precursors 7. L-1 and peptides containing L-1 are inhibitors of the enzyme glutamine synthetase (GS). Inhibition of GS is responsible for the antibiotical and herbicidal properties of these compounds. Synthesis of substrates 7 and parameters influencing the enantioselectivity are discussed. Substrate concentration and solvent polarity appear to have the most marked effects on enantiomeric excesses for a given catalyst system. Enantiomeric excesses reach 91 % for hydrogenations with (R,R)-NORPHOS- and (S,S)-CHIRAPHOS-derived catalysts.

  DOI：

  10.1021/jo00005a024

文献信息

• Enantioselective synthesis of both enantiomers of phosphinothricin via asymmetric hydrogenation of .alpha.-acylamido acrylates
  作者：Hans Joachim Zeiss

  DOI：10.1021/jo00005a024

  日期：1991.3

  Both enantiomers of phosphinothricin (1), a naturally occuring amino acid that contains the unique methylphosphinate moiety, were prepared by asymmetric hydrogenation of alpha-acylamido acrylate precursors 7. L-1 and peptides containing L-1 are inhibitors of the enzyme glutamine synthetase (GS). Inhibition of GS is responsible for the antibiotical and herbicidal properties of these compounds. Synthesis of substrates 7 and parameters influencing the enantioselectivity are discussed. Substrate concentration and solvent polarity appear to have the most marked effects on enantiomeric excesses for a given catalyst system. Enantiomeric excesses reach 91 % for hydrogenations with (R,R)-NORPHOS- and (S,S)-CHIRAPHOS-derived catalysts.