ethyl (2'R)-2-carboethoxy-3-(tetrahydro-2'-furyl)propanoate | 71862-15-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (2'R)-2-carboethoxy-3-(tetrahydro-2'-furyl)propanoate
• 英文别名: (R)-diethyl 2-((tetrahydrofuran-2-yl)methyl)malonate；diethyl 2-[[(2R)-oxolan-2-yl]methyl]propanedioate
• CAS: 71862-15-2
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: DNNUDKVYVAZVKN-SECBINFHSA-N

物化性质

• 沸点：
  304.6±12.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2'R)-2-carboethoxy-3-(tetrahydro-2'-furyl)propanoate 在 R(+)-alpha-甲基苄胺 、 sodium hydride 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 5.5h， 生成 2-(diethylamino)ethyl (2R)-2-(naphthalen-1-ylmethyl)-3-[(2R)-oxolan-2-yl]propanoate;oxalic acid
  参考文献：
  名称：

  Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor

  摘要：

  Naftidrofuryl oxalate (Praxilene (R), 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (2-HT2) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT2A receptor, and the C-2' configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT2A receptor that have clinical significance as vasodilators and CNS agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.093
• 作为产物：
  描述：

  四氢糠醇 在 吡啶 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 ethyl (2'R)-2-carboethoxy-3-(tetrahydro-2'-furyl)propanoate
  参考文献：
  名称：

  Intramolecular acylative ring-switching reactions of 3-(tetrahydro-2′-furyl)propanoic acid derivatives to give butanolides: mechanism and scope

  摘要：

  当3-(四氢-2′-呋喃基)丙酸-三氟乙酸混合酐在酸催化剂的作用下生成二氢-5-(3′-三氟乙酰氧基丙基)-2(3H)-呋喃酮的机制被定义，并描述了一些潜在有用的丁内酯合成体的合成途径。

  DOI：

  10.1039/b301329b

文献信息

• Intramolecular acylative ring-switching reactions of 3-(tetrahydro-2′-furyl)propanoic acid derivatives to give butanolides: mechanism and scope
  作者：David H. Grayson、Úna McCarthy、Edwin D. Roycroft

  DOI：10.1039/b301329b

  日期：——

  The mechanism by which dihydro-5-(3′-trifluoroacetoxypropyl)-2(3H)-furanone is formed when 3-(tetrahydro-2′-furyl)propanoic-trifluoroacetic mixed anhydride is treated with an acidic catalyst is defined, and routes to some potentially useful butanolide synthons are described.

  当3-(四氢-2′-呋喃基)丙酸-三氟乙酸混合酐在酸催化剂的作用下生成二氢-5-(3′-三氟乙酰氧基丙基)-2(3H)-呋喃酮的机制被定义，并描述了一些潜在有用的丁内酯合成体的合成途径。
• Practical access to four stereoisomers of naftidrofuryl and their binding affinity towards 5-hydroxytryptamine 2A receptor
  作者：Jia Hao、Bo Chen、Yiwu Yao、Murad Hossain、Takafumi Nagatomo、Hequan Yao、Lingyi Kong、Hongbin Sun

  DOI：10.1016/j.bmcl.2012.03.093

  日期：2012.5

  Naftidrofuryl oxalate (Praxilene (R), 1) has been used for the treatment of intermittent claudication for more than 30 years. It selectively blocks vascular and platelet 5-hydroxytryptamine 2 (2-HT2) receptors. This drug is marketed as a mixture of four stereoisomers, and so far there is no individual biological evaluation on the single isomers. The purpose of this study is to provide an improved method for the preparation of all four stereoisomers of naftidrofuryl, and more importantly, to distinguish them in terms of their binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor. The bioassay results revealed that the C-2S configuration of naftidrofuryl was crucial for the binding affinity with 5-HT2A receptor, and the C-2' configuration was less important for binding. In conclusion, our study may pave the way to develop single naftidrofuryl isomers with C-2S configuration as inhibitors of 5-HT2A receptor that have clinical significance as vasodilators and CNS agents. (C) 2012 Elsevier Ltd. All rights reserved.