(5-Methyl-furan-3-yl)-phosphonic acid diethyl ester | 189117-33-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (5-Methyl-furan-3-yl)-phosphonic acid diethyl ester
• 英文别名: 4-Diethoxyphosphoryl-2-methylfuran
• CAS: 189117-33-7
• 化学式: C₉H₁₅O₄P
• 分子量: 218.189
• InChiKey: DBMYAIVIFYJGOC-UHFFFAOYSA-N

物化性质

• 沸点：
  278.1±28.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-Methyl-furan-3-yl)-phosphonic acid diethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以96%的产率得到(5-Bromomethyl-furan-3-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Phosphofurylalanine, a stable analog of phosphohistidine

  摘要：

  Phosphorylated histidine residues occur in a number of signal-transduction pathways in bacteria as well as in eukaryotes. Phosphohistidine is hydrolytically labile and therefore difficult to study, this by contrast to stable phosphoserine, phosphothreonine or phosphotyrosine. Here we report the design and enantioselective synthesis of (4'-phospho-2'-furyl)alanine I, a non-hydrolyzable analog of 1-phosphohistidine. This novel amino-acid should be useful to synthesize peptides incorporating a stable analog phosphohistidine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00209-7
• 作为产物：
  描述：

  diethyl 3,3-diethoxybutylphosphonate 在 盐酸 、 Amberlyst 15 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 13.5h， 生成 (5-Methyl-furan-3-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  A Simple and Efficient Synthesis of 2-Substituted 3-Diethylphosphono 5-Methylfurans

  摘要：

  An efficient carbanionic synthesis of the phosphonic dicarbonylated compounds 2 was achieved and used as key intermediates in the synthesis of the phosphonic furans 4 by acid-induced Paal-Knorr cyclization reaction.

  DOI：

  10.1080/00397919708003353

文献信息

• A Simple and Efficient Synthesis of 2-Substituted 3-Diethylphosphono 5-Methylfurans
  作者：Isabelle Truel、Abdourahman Mohamed-Hachi、Elie About-Jaudet、Noël Collignon

  DOI：10.1080/00397919708003353

  日期：1997.4

  An efficient carbanionic synthesis of the phosphonic dicarbonylated compounds 2 was achieved and used as key intermediates in the synthesis of the phosphonic furans 4 by acid-induced Paal-Knorr cyclization reaction.
• Phosphofurylalanine, a stable analog of phosphohistidine
  作者：Caroline Schenkels、Bernhard Erni、Jean-Louis Reymond

  DOI：10.1016/s0960-894x(99)00209-7

  日期：1999.5

  Phosphorylated histidine residues occur in a number of signal-transduction pathways in bacteria as well as in eukaryotes. Phosphohistidine is hydrolytically labile and therefore difficult to study, this by contrast to stable phosphoserine, phosphothreonine or phosphotyrosine. Here we report the design and enantioselective synthesis of (4'-phospho-2'-furyl)alanine I, a non-hydrolyzable analog of 1-phosphohistidine. This novel amino-acid should be useful to synthesize peptides incorporating a stable analog phosphohistidine. (C) 1999 Elsevier Science Ltd. All rights reserved.