3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid | 138965-46-5

• 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: 3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid
• 英文别名: 3-[(4S)-5-oxo-3-prop-2-enoxycarbonyl-1,3-oxazolidin-4-yl]propanoic acid
• CAS: 138965-46-5
• 化学式: C₁₀H₁₃NO₆
• 分子量: 243.216
• InChiKey: VFXMUVFVVSZLIJ-ZETCQYMHSA-N

物化性质

• 沸点：
  477.7±40.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid 在 四(三苯基膦)钯 sodium 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 L-谷氨酸
  参考文献：
  名称：

  Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid

  摘要：

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.

  DOI：

  10.1021/ja971568j
• 作为产物：
  描述：

  聚合甲醛 、 (S)-N-allyloxycarbonylglutamic acid 在 对甲苯磺酸 作用下， 反应 1.0h， 生成 3-[3-((allyloxy)carbonyl)-5-oxo-1,3-oxazolan-4-yl]propanoic acid
  参考文献：
  名称：

  Regioselective Amidation of Aspartic and Glutamic Acid

  摘要：

  本发明描述了以天冬氨酸和谷氨酸为原料，通过 5-oxazolidinone 衍生物中间体与水氨或胺的区域选择性酰胺化反应，合成 N 保护的天冬 1-酰胺和谷氨酸 1-酰胺的过程。

  DOI：

  10.1055/s-1991-26610

文献信息

• Synthesis of 5-oxo-l-pipecolic acid derivatives by rhodium(II) acetate catalyzed cyclization of diazoketones
  作者：Kwang-Youn Ko、Kee-In Lee、Wan-Loo Kim

  DOI：10.1016/s0040-4039(00)61009-2

  日期：1992.10

  A convenient synthesis of 5-oxo-L-pipecolic acid derivatives is described. The key step involves the rhodium(II) acetate catalyzed N-H insertion reaction of diazoketones, which are derived from L-glutamic acid.
• Solid-Phase Synthesis via 5-Oxazolidinones. Ring-Opening Reactions with Amines and Reaction Monitoring by Single-Bead FT-IR Microspectroscopy
  作者：Roger E. Marti、Bing Yan、Mark A. Jarosinski

  DOI：10.1021/jo9623503

  日期：1997.8.1
• Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid
  作者：Jin Luo、Michael D. Smith、Douglas A. Lantrip、Susan Wang、P. L. Fuchs

  DOI：10.1021/ja971568j

  日期：1997.10.1

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.
• Regioselective Amidation of Aspartic and Glutamic Acid
  作者：Kee-In Lee、Jae Hak Kim、Kwang-Youn Ko、Wan-Joo Kim

  DOI：10.1055/s-1991-26610

  日期：——

  The synthesis of N-protected aspartic 1-amide and glutamic 1-amide from aspartic and glutamic acids via regioselective amidation of intermediate 5-oxazolidinone derivatives with aqueous ammonia or amine is described.

  本发明描述了以天冬氨酸和谷氨酸为原料，通过 5-oxazolidinone 衍生物中间体与水氨或胺的区域选择性酰胺化反应，合成 N 保护的天冬 1-酰胺和谷氨酸 1-酰胺的过程。