2,5-Bis(carbethoxy)pentane-1-phosphinic acid | 159395-40-1

• 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: 2,5-Bis(carbethoxy)pentane-1-phosphinic acid
• 英文别名: 2,4-bis(ethoxycarbonyl)butylphosphinic acid；2,4-bis(ethyloxycarbonyl)butylphosphonic acid；(5-Ethoxy-2-ethoxycarbonyl-5-oxopentyl)phosphinic acid
• CAS: 159395-40-1
• 化学式: C₁₀H₁₉O₆P
• 分子量: 266.231
• InChiKey: VBYJDNHAJXEONO-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  95.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-Bis(carbethoxy)pentane-1-phosphinic acid 在 乙酸酐 、 对甲苯磺酸 、 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 1-(N-ethyloxycarbonyl)amino-3-methylthiopropyl-2,4-bis(ethyloxycarbonyl)butylphosphinic acid P-adamantyl ester
  参考文献：
  名称：

  次磷酸假甲硫氨酰-谷氨酰-组氨酸的合成

  摘要：

  摘要 提出使用氨基甲酸乙酯和 3-(甲硫基)丙醛对含有谷氨酸二乙酯结构等排体的亚膦酸进行酰胺烷基化，以合成 NC(O)OEt 保护的次膦假 Met-Glu 肽。随后对磷酸功能的金刚烷基保护和羧基的水解使得获得环状谷氨酸酐形式的次膦酸Met-[P]-Glu肽成为可能。发现后者与第三种氨基酸成分组氨酸反应形成次膦酸Met-[P]-Glu-γ-His三肽。

  DOI：

  10.1134/s1070363223080108
• 作为产物：
  描述：

  在 乙醇 作用下， 以 水 为溶剂， 生成 2,5-Bis(carbethoxy)pentane-1-phosphinic acid
  参考文献：
  名称：

  Synthesis of phosphorus isosters of β-amyloid peptides fragments

  摘要：

  We have developed a synthetic route to pseudo dipeptides, analogs of certain fragments of beta-amyloid peptides (products of the APP protein hydrolysis). These compounds can be used for preparation of phosphinic acidic oligopeptides representing the peptide sequence of the beta-amyloid but containing the phosphorus isoster peptide fragment. Synthesis of pseudo ornityl-glutamate, pseudo arginyl-glutamate, pseudo glycyl-leucine, and pseudo isoleucyl-glycine via amino- and amidoalkylation of phosphonic acids containing the structural isoster of the corresponding amino acid is described.

  DOI：

  10.1134/s1070363215090121

文献信息

• The Chemistry of Phosphapeptides: Investigations on the Synthesis of Phosphonamidate, Phosphonate, and Phosphinate Analogs of Glutamyl-.gamma.-glutamate
  作者：William P. Malachowski、James K. Coward

  DOI：10.1021/jo00104a017

  日期：1994.12

  The synthesis of the phosphonamidate, 1d, and phosphonate, 1e, analogues of a gamma-glutamyl peptide are reported. Michaelis-Arbuzov reaction with the alkyl halide, 7b, derived from L-glutamic acid, yielded dimethyl phosphonate, 8b. Selective aminolysis of the phosphorus diester provided monomethyl phosphonic acid, 9. Utilizing the methodology developed in the accompanying paper, 9 was converted to the phosphonochloridate, 10. Subsequent reaction with diethyl glutamic acid and hydrogenation afforded the complex phosphonamidate, 1d. Mitsunobu coupling of the monomethyl phosphonic acid, 9, with diethyl 2-hydroxyglutarate, followed by hydrogenation, provided the complex mixed phosphonate, 1e.
• Synthesis of prolyl-glutamate phosphoisostere
  作者：M. E. Dmitriev、A. V. Vinyukov、B. V. Lednev、V. V. Ragulin

  DOI：10.1134/s1070363217100358

  日期：2017.10

  A method for the synthesis of prolyl-glutamate phosphoisostere by cyclic amidoalkylation of phosphonous acid containing a structural isostere of glutamic acid was developed. A combination of amide and carbonyl moieties in the 4-N-Cbz-aminobutyraldehyde molecule allows cyclization with in situ generation of a cyclic pyrrolidine Schiff base followed by its Arbuzov type phosphorylation.