4-氨基-4-膦酰丁酸 | 18865-31-1

• 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
• 中文名称: 4-氨基-4-膦酰丁酸
• 英文名称: 4-amino-4-phosphonobutanoic acid
• 英文别名: 4-Amino-4-phosphonobutyric acid；4-amino-4 phosphonobutyric acid；α-Amino-γ-carboxypropylphosphorsaeure
• CAS: 18865-31-1
• 化学式: C₄H₁₀NO₅P
• 分子量: 183.101
• InChiKey: SODXFOVXZATGPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-氨基-4-膦酰丁酸 在 氯化亚砜 作用下， 以84%的产率得到methyl 4-amino-4-phosphonobutyrate
  参考文献：
  名称：

  New phosphonic analogs of aspartic and glutamic acid by aminoalkylation of trivalent phosphorus chlorides with ethyl acetyloacetate or ethyl levulinate and benzyl carbamate

  摘要：

  DOI：

  10.1007/bf00814338
• 作为产物：
  描述：

  5-phosphono-2-pyrrolidone 在 水 作用下， 反应 100.0h， 以77.1%的产率得到4-氨基-4-膦酰丁酸
  参考文献：
  名称：

  [EN] METHOD FOR THE SYNTHESIS OF ALPHA-AMINOALKYLENEPHOSPHONIC ACID
  [FR] PROCÉDÉ DE SYNTHÈSE D'ACIDE ALPHA-AMINOALKYLÈNEPHOSPHONIQUE

  摘要：

  本发明涉及一种合成α-氨基烯基膦酸或其膦酸酯的新方法，包括以下步骤：通过混合含有一个P原子在氧化态（+111）和另一个P原子在氧化态（+111）或（+V）的P-O-P酸酐基团的化合物、氨基烷基羧酸和酸催化剂来形成反应混合物，其中所述反应混合物中α-氨基烯基羧酸与P-O-P酸酐基团的当量比至少为0.2，并从反应混合物中回收所得的α-氨基烯基膦酸化合物或其酯。

  公开号：

  WO2014012990A1

文献信息

• [EN] METHOD FOR THE SYNTHESIS OF ALPHA-AMINOALKYLENEPHOSPHONIC ACID<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'ACIDE ALPHA-AMINOALKYLÈNEPHOSPHONIQUE
  申请人：STRAITMARK HOLDING AG

  公开号：WO2014012990A1

  公开（公告）日：2014-01-23

  The present invention is related to a new method for the synthesis of alpha-aminoalkylenephosphonic acid or its phosphonate esters comprising the steps of forming a reaction mixture by mixing a P-O-P anhydride moiety comprising compound, having one P-atom at the oxidation state (+111) and the other P-atom at the oxidation state (+111) or (+V), an aminoalkanecarboxylic acid and an acid catalyst, wherein said reaction mixture comprises an equivalent ratio of alpha-aminoalkylene carboxylic acid to P-O-P anhydride moieties of at least 0.2, and recovering the resulting alpha-aminoalkylene phosphonic acid compound or an ester thereof from the reaction mixture.

  本发明涉及一种合成α-氨基烯基膦酸或其膦酸酯的新方法，包括以下步骤：通过混合含有一个P原子在氧化态（+111）和另一个P原子在氧化态（+111）或（+V）的P-O-P酸酐基团的化合物、氨基烷基羧酸和酸催化剂来形成反应混合物，其中所述反应混合物中α-氨基烯基羧酸与P-O-P酸酐基团的当量比至少为0.2，并从反应混合物中回收所得的α-氨基烯基膦酸化合物或其酯。
• Organophosphorus analogs of biologically active compounds
  作者：R. M. Khomutov、T. I. Osipova、Yu. N. Zhukov、I. A. Gandurina

  DOI：10.1007/bf00952486

  日期：1979.9
• A practical synthesis of α-aminophosphonic acids.
  作者：J.P. Genêt、J. Uziel、M. Port、A.M. Touzin、S. Roland、S. Thorimbert、S. Tanier

  DOI：10.1016/s0040-4039(00)77677-5

  日期：1992.1

  The preparation of diterbutyl-N (diphenylmethylene) aminomethylphosphonate 3 in four steps (42% overall yield) from N-hydroxymethyl phtalimide 1 is described. Various alpha-substituted alpha-aminophosphonic acids 5 containing functionalized unsaturated chains have been synthesized by alkylation of 3 under phase transfer catalysis with halides, Michael acceptors and palladium promoted reactions, followed by mild hydrolysis.
• Diel, Peter J.; Maier, Ludwig, Phosphorus and Sulfur and the Related Elements, 1987, vol. 29, p. 201 - 210
  作者：Diel, Peter J.、Maier, Ludwig

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
  作者：Frank R. Atherton、Cedric H. Hassall、Robert W. Lambert

  DOI：10.1021/jm00151a005

  日期：1986.1

  Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1, Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanine, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and rare amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P) (45). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) (46) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.