2-Acetamido-3-ethoxy-2-(naphthalen-1-ylmethyl)-3-oxopropanoic acid | 136015-49-1

• 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: 2-Acetamido-3-ethoxy-2-(naphthalen-1-ylmethyl)-3-oxopropanoic acid
• CAS: 136015-49-1
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: ZXGHVLYAQZOLJB-UHFFFAOYSA-N

物化性质

• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Acetamido-3-ethoxy-2-(naphthalen-1-ylmethyl)-3-oxopropanoic acid 在 盐酸 作用下， 反应 2.17h， 生成 3-(1-萘基)-L-丙氨酸
  参考文献：
  名称：

  Synthesis and biological activities of cholecystokinin analogues substituted in position 30 by 3-(1-naphthyl)-l-alanine [Nal(1)] or 3-(2-naphthyl)-l-alanine [Nal(2)]

  摘要：

  Acetyl derivatives of ethyl esters of 3-(1-naphthyl)-D,L-alanine and 3-(2-naphthyl)-D,L-alanine were synthesized through a malonic condensation. Resolution of these derivatives by subtilisin Carlsberg followed by acid hydrolysis afforded the 2 optical isomers of 3-(1-naphthyl)-alanine [Nal(1)] and 3-(2-naphthyl)-alanine [Nal(2)]. The L enantiomers of these amino acids were incorporated into the sequence of cholecystokinin in place of the tryptophan in position 30. The cholecystokinin analogues thus obtained behaved as full agonists, with reduced potencies on rat pancreatic acini and on guinea pig brain membranes, by about one order of magnitude for the Nal(2) derivative and by 2 orders of magnitude for the Nal(1) derivative, as compared to the potent parent compound Boc-Tyr(SO3H)-Nle-Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/0223-5234(91)90056-s
• 作为产物：
  描述：

  1-溴甲基萘 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-Acetamido-3-ethoxy-2-(naphthalen-1-ylmethyl)-3-oxopropanoic acid
  参考文献：
  名称：

  Synthesis and biological activities of cholecystokinin analogues substituted in position 30 by 3-(1-naphthyl)-l-alanine [Nal(1)] or 3-(2-naphthyl)-l-alanine [Nal(2)]

  摘要：

  Acetyl derivatives of ethyl esters of 3-(1-naphthyl)-D,L-alanine and 3-(2-naphthyl)-D,L-alanine were synthesized through a malonic condensation. Resolution of these derivatives by subtilisin Carlsberg followed by acid hydrolysis afforded the 2 optical isomers of 3-(1-naphthyl)-alanine [Nal(1)] and 3-(2-naphthyl)-alanine [Nal(2)]. The L enantiomers of these amino acids were incorporated into the sequence of cholecystokinin in place of the tryptophan in position 30. The cholecystokinin analogues thus obtained behaved as full agonists, with reduced potencies on rat pancreatic acini and on guinea pig brain membranes, by about one order of magnitude for the Nal(2) derivative and by 2 orders of magnitude for the Nal(1) derivative, as compared to the potent parent compound Boc-Tyr(SO3H)-Nle-Gly-Trp-Nle-Asp-Phe-NH2.

  DOI：

  10.1016/0223-5234(91)90056-s

文献信息

• Synthesis of 3-Substituted 2,3-Dehydroprolines: Oxidative Decarboxylation of Ethyl Hydrogen Acetoamidomalonate Derivatives
  作者：Satoshi Osada、Takeshi Fumoto、Hiroaki Kodama、Michio Kondo

  DOI：10.1246/cl.1998.675

  日期：1998.7

  A new synthetic method for α,β-dehydroamino acid derivatives have been accomplished via lead(IV) tetraacetate oxidation of ethyl hydrogen acetoamidomalonate derivatives in the presence of copper(II) acetate. Four 3-substituted 2,3-dehydroprolines have been synthesized by this oxidative decarboxylation.

  在乙酸铜 (II) 存在下，通过四乙酸铅 (IV) 氧化乙酰氨基丙二酸乙酯衍生物，实现了一种合成 α,β-脱氢氨基酸衍生物的新方法。通过这种氧化脱羧作用合成了四个 3-取代的 2,3-脱氢脯氨酸。