1-羟乙基膦酸 | 20188-02-7

• 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
• 中文名称: 1-羟乙基膦酸
• 英文名称: (1-hydroxyethyl)phosphonic acid
• 英文别名: 1-hydroxyethylphosphonic acid
• CAS: 20188-02-7
• 化学式: C₂H₇O₄P
• mdl: MFCD27952823
• 分子量: 126.049
• InChiKey: ZBURELSAUHPHKC-UHFFFAOYSA-N

物化性质

• 沸点：
  354.7±44.0 °C(Predicted)
• 密度：
  1.603±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-羟乙基膦酸 在 氧气 作用下， 反应 2.0h， 生成 乙酰磷酸
  参考文献：
  名称：

  Hydroperoxylation by Hydroxyethylphosphonate Dioxygenase

  摘要：

  Hydroxyethylphosphonate dioxygenase (HEPD) catalyzes the O-2-dependent cleavage of the carbon-carbon bond of 2-hydroxyethylphosphonate (2-HEP) to afford hydroxymethylphosphonate (HMP) and formate without input of electrons or use of any organic cofactors. Two mechanisms have been proposed to account for this reaction. One involves initial hydroxylation of substrate to an acetal intermediate and its subsequent attack onto an Fe(IV)-oxo species. The second mechanism features initial hydroperoxylation of substrate followed by a Criegee rearrangement. To distinguish between the two mechanisms, substrate analogues were synthesized and presented to the enzyme. Hydroxymethylphosphonate was converted into phosphate and formate, and 1 -hydroxyethylphosphonate was converted to acetylphosphate, which is an inhibitor of the enzyme. These results provide strong support for a Criegee rearrangement with a phosphorus-based migrating group and require that the O-O bond of molecular oxygen is not cleaved prior to substrate activation. (2R)-Hydroxypropylphosphonate partitioned between conversion to 2-oxopropylphosphonate and hydroxymethylphosphonate, with the latter in turn converted to phosphate and formate. Collectively, these results support a mechanism that proceeds by hydroperoxylation followed by a Criegee rearrangement.

  DOI：

  10.1021/ja906238r
• 作为产物：
  描述：

  三聚乙醛 在 亚磷酸 作用下， 生成 1-羟乙基膦酸
  参考文献：
  名称：

  Marie, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1903, vol. 136, p. 48

  摘要：

  DOI：

文献信息

• [EN] METHOD FOR THE MANUFACTURE OF COMPOUNDS CONTAINING AN a-OXY PHOSPHORUS GROUP<br/>[FR] PROCÉDÉ POUR LA FABRICATION DE COMPOSÉS CONTENANT UN GROUPE ?-OXY-PHOSPHORÉ
  申请人：STRAITMARK HOLDING AG

  公开号：WO2012098255A1

  公开（公告）日：2012-07-26

  A method for the manufacture of compounds containing an α-oxy phosphorus group is disclosed. A P-O component having at least one P-O-P moiety, whereby at least one phosphorus has the +3 oxidation state, is added in specific proportions to a compound containing an α-oxy carboxylic acid group, followed by conducting the reaction and adding water subsequently. The compounds containing an α-oxy phosphorus group formed can then be recovered.

  披露了一种含有α-氧磷基团的化合物的制造方法。将至少含有一个P-O-P基团的P-O组分，其中至少一个磷处于+3氧化态，按特定比例添加到含有α-氧羧酸基团的化合物中，然后进行反应并在随后加入水。随后可以回收形成的含有α-氧磷基团的化合物。
• A Simple, Efficient Synthesis of Dibenzyl and Di-<i>p</i>-nitrobenzyl 1-Hydroxyalkanephosphonates
  作者：Maria Hoffmann

  DOI：10.1055/s-1988-33434

  日期：——

  Dibenzyl and di-p-nitrobenzyl 1-hydroxyalkanephosphonates 3a-i are prepared by alkylation of 1-hydroxyalkanephosphonic acids 1 with O-benzyl and O-(p-nitrobenzyl)-N,N′-dicyclohexylisoureas 2.

  二苯基和二对硝基苯基1-羟基烷基磷酸酯3a-i是通过将1-羟基烷基磷酸一酸1与O-苄基和O-(对硝基苯基)-N,N′-二环己基异脲2进行烷基化反应制备的。
• Use of the dehydrophos biosynthetic enzymes to prepare antimicrobial analogs of alaphosphin
  作者：Despina J. Bougioukou、Chi P. Ting、Spencer C. Peck、Subha Mukherjee、Wilfred A. van der Donk

  DOI：10.1039/c8ob02860e

  日期：——

  enzyme is also tolerant with respect to the amino acid attached to tRNALeu. Using a mutant of leucyl tRNA synthetase that is deficient in its proofreading ability allowed the preparation of a series of aminoacyl-tRNALeu derivatives (Ile, Ala, Val, Met, norvaline, and norleucine). DhpH-C accepted these aminoacyl-tRNA derivatives and condensed the amino acid with l-Ala(P) to form the corresponding phosphonodipeptides

  脱磷生物合成酶DhpH（DhpH-C）的C末端结构域催化Leu-tRNALeu与（R）-1-氨基乙基膦酸酯（丙氨酸的氨基膦酸酯类似物Ala（P））缩合。该反应的产物Leu-Ala（P）是磷酸二肽，一类化合物，以前已被研究用作临床抗生素。在这项研究中，我们表明DhpH-C具有高度的底物耐受性，并且可以将各种氨基膦酸酯（Gly（P），Ser（P），Val（P），1-氨基-丙基膦酸酯和苯基甘氨酸（P））缩合到Leu。而且，该酶对tRNALeu上连接的氨基酸也具有耐受性。使用缺乏校对能力的亮氨酰tRNA合成酶突变体，可以制备一系列氨酰基-tRNALeu衍生物（Ile，Ala，Val，Met，正缬氨酸和正亮氨酸）。DhpH-C接受这些氨基酰基-tRNA衍生物，并将氨基酸与1-Ala（P）缩合形成相应的磷酸二肽。这些肽的一部分显示出抗微生物活性，表明该酶是制备抗微生物肽的通用生物催化剂。我们还研究了来
• THE FORMATION OF α-AMINO AND α-HYDROXY-ALKANEPHOSPHONIC ACIDS IN THE REACTIONS OF PHOSPHITE ESTERS WITH ALDEHYDES AND ALKYL CARBAMATES
  作者：Harry R. Hudson、Fatima Ismail、Max Pianka、Chi-Wai Wan

  DOI：10.1080/10426500008045250

  日期：2000.1

  Abstract The preparation of α-aminoalkanephosphonic acids from triphenyl phosphite, an aldehyde, and ethyl or benzyl carbamate in glacial acetic acid, followed by hydrolysis, is accompanied by the formation of the corresponding α-hydroxyphosphonic acid. Reaction in toluene, using boron trifluoride-etherate as catalyst, affords an alternative reparative procedure but does not prevent the formation of

  摘要 由亚磷酸三苯酯、醛和氨基甲酸乙酯或苄酯在冰醋酸中制备α-氨基烷烃膦酸，然后水解，同时生成相应的α-羟基膦酸。在甲苯中反应，使用三氟化硼醚合物作为催化剂，提供了另一种修复程序，但不能阻止 α-羟基膦酸的形成。31P nmr 揭示了许多中间体的存在。讨论了反应。
• Deamination of 1-Aminoalkylphosphonic Acids: Reaction Intermediates and Selectivity
  作者：Anna Brol、Tomasz K. Olszewski

  DOI：10.3390/molecules27248849

  日期：——

  acids in the reaction with HNO2 (generated "in situ" from NaNO2) yields a mixture of substitution products (1-hydroxyalkylphosphonic acids), elimination products (vinylphosphonic acid derivatives), rearrangement and substitution products (2-hydroxylkylphosphonic acids) as well as H3PO4. The variety of formed reaction products suggests that 1-phosphonoalkylium ions may be intermediates in such deamination

  1-氨基烷基膦酸在与 HNO2 的反应中脱氨（从 NaNO2“原位”生成）产生取代产物（1-羟基烷基膦酸）、消除产物（乙烯基膦酸衍生物）、重排和取代产物（2-羟基烷基膦酸）的混合物) 以及 H3PO4。形成的各种反应产物表明 1-phosphonoalkylium 离子可能是此类脱氨反应的中间体。