α-hydroxypropanephosphonic acid | 53621-85-5

• 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: α-hydroxypropanephosphonic acid
• 英文别名: (1-hydroxy-propyl)-phosphonic acid；(1-Hydroxy-propyl)-phosphonsaeure；Oxypropylphosphinsaeure；1-Hydroxypropylphosphorsaeure；Oxypropanephosphonic acid；1-hydroxypropylphosphonic acid
• CAS: 53621-85-5
• 化学式: C₃H₉O₄P
• mdl: MFCD29950538
• 分子量: 140.076
• InChiKey: MVIJUJBSAAUHEM-UHFFFAOYSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  338.6±44.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  8
• 可旋转键数：
  2
• 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：

  α-hydroxypropanephosphonic acid 在 氨 、 calcium chloride 作用下， 生成 (1-hydroxy-propyl)-phosphonic acid ; calcium compound
  参考文献：
  名称：

  Fossek, Monatshefte fur Chemie, 1886, vol. 7, p. 34

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl 1-hydroxypropylphosphonate 在 盐酸 作用下， 以93 %的产率得到α-hydroxypropanephosphonic acid
  参考文献：
  名称：

  Identification and analysis of small molecule inhibitors of FosB from Staphylococcus aureus

  摘要：

  高通量虚拟筛选从耐甲氧西林金黄色葡萄球菌中发现了几种新的 FosB 抑制剂。

  DOI：

  10.1039/d3md00113j

文献信息

• SILYL PHOSPHITES V. THE REACTIONS OF TRIS(TRIMETHYLSILYL) PHOSPHITE WITH CARBONYL COMPOUNDS
  作者：Mitsuo Sekine、Isamu Yamamoto、Akio Hashizume、Tsujiaki Hata

  DOI：10.1246/cl.1977.485

  日期：1977.5.5

  When tris(trimethylsilyl) phosphite (1) was treated with aldehydes, ketones, or α,β-unsaturated aldehydes at room temperature, the 1,2-adducts were obtained in high yields (75–94%). On the other hand, when α,β-unsaturated ketones or ethyl crotonate was used, the 1,4-adducts were obtained in high yields (71–84%). The silylated products were smoothly hydrolyzed to the corresponding phosphonates in almost

  当亚磷酸三（三甲基甲硅烷基）酯 (1) 在室温下用醛、酮或 α,β-不饱和醛处理时，1,2- 加合物以高产率 (75-94%) 获得。另一方面，当使用 α,β-不饱和酮或巴豆酸乙酯时，1,4-加合物的产率很高（71-84%）。通过添加醇或水，硅烷化产物以几乎定量的产率顺利水解为相应的膦酸酯。
• Studies on the biodegradation of fosfomycin: Growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically
  作者：John W. McGrath、Friedrich Hammerschmidt、Werner Preusser、John P. Quinn、Anna Schweifer

  DOI：10.1039/b821829c

  日期：——

  The first step of the mineralisation of fosfomycin by R. huakuii PMY1 is hydrolytic ring opening with the formation of (1R,2R)-1,2-dihydroxypropylphosphonic acid. This phosphonic acid and its three stereoisomers were synthesised by chemical means and tested as their ammonium salts for mineralisation as evidenced by release of Pi. Only the (1R,2R)-isomer was degraded. A number of salts of phosphonic acids such as (±)-1,2-epoxybutyl-, (±)-1,2-dihydroxyethyl-, 2-oxopropyl-, (S)-2-hydroxypropyl-, (±)-1-hydroxypropyl- and (±)-1-hydroxy-2-oxopropylphosphonic acid were synthesised chemically, but none supported growth. In vitro C–P bond cleavage activity was however detected with the last phosphonic acid. A mechanism involving phosphite had to be discarded as it could not be used as a phosphorus source. R. huakuii PMY1 grew well on (R)- and (S)-lactic acid and hydroxyacetone, but less well on propionic acid and not on acetone or (R)- and (±)-1,2-propanediol. The Pi released from (1R,2R)-1,2-dihydroxypropylphosphonic acid labelled with one oxygen-18 in the PO3H2group did not stay long enough in the cells to allow complete exchange of 18O for 16O by enzymic turnover.

  R. huakuii PMY1 矿化磷霉素的第一步是水解开环，形成 (1R,2R)-1,2-二羟基丙基膦酸。通过化学方法合成了这种膦酸及其三种立体异构体，并测试了它们作为铵盐的矿化作用，Pi 的释放证明了这一点。只有 (1R,2R)-异构体被降解。化学合成了一些膦酸盐，如(±)-1,2-环氧丁基-、(±)-1,2-二羟乙基-、2-氧代丙基-、(S)-2-羟基丙基-、(±)-1-羟基丙基-和(±)-1-羟基-2-氧代丙基膦酸，但没有一种能支持生长。不过，在最后一种膦酸中检测到了体外 C-P 键裂解活性。由于亚磷酸不能用作磷源，因此必须放弃涉及亚磷酸的机制。R. huakuii PMY1 在(R)-和(S)-乳酸和羟基丙酮上生长良好，但在丙酸上生长较差，在丙酮或(R)-和(±)-1,2-丙二醇上生长不良。从(1R,2R)-1,2-二羟基丙基膦酸中释放出的 Pi 在 PO3H2 组中标记了一个氧-18，但在细胞中停留的时间不够长，无法通过酶的转换将 18O 完全交换为 16O。
• 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。
• Schuelke, Ulrich, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 51/52, p. 623 - 626
  作者：Schuelke, Ulrich

  DOI：——

  日期：——