(α-amino-4-fluorobenzyl)phosphonic acid | 125553-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (α-amino-4-fluorobenzyl)phosphonic acid
• 英文别名: α-amino-(4'-fluorophenyl-)methanephosphonic acid；[amino-(4-fluorophenyl)methyl]phosphonic acid
• CAS: 125553-06-2
• 化学式: C₇H₉FNO₃P
• mdl: MFCD24388558
• 分子量: 205.126
• InChiKey: VNELARWUCSOVHC-UHFFFAOYSA-N

物化性质

• 熔点：
  298-300 °C
• 沸点：
  408.0±55.0 °C(Predicted)
• 密度：
  1.536±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (α-amino-4-fluorobenzyl)phosphonic acid 在 sodium hydroxide 、 penicillin G acylase from E_. coli 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 (R)-(α-amino(4-fluorophenyl)methyl)phosphonic acid
  参考文献：
  名称：

  RESOLUTION OF FLUORINATED AMINOMETHANPHOSPHONIC ACIDS CATALYSED BY PENICILLIN G ACYLASE - III

  摘要：

  In this work, we have used penicillin G acylase (EC 3.5.1.11) from E. coli to resolve kinetically four fluorinated aminomethanphosphonic acids: 1: 1-trifluoromethyl-, 2:1-p-fluorophenyl-, 3:1-m-fluorophenyl-, 4: 1-p-trifluoromethylphenyl-1-aminomethanphosphonic acids. This enzyme catalyses enantioselectively the hydrolysis of the N-phenylacetylated derivatives of 1-4, The enantiomeric excesses determined via P-31 NMR spectra of the diastereomeric Pd(II) complexes of 1-4 were high for each compound studied.

  DOI：

  10.1080/10426509708043557
• 作为产物：
  描述：

  O,O-diethyl-N-benzylamino-4-fluorophenylmethylphosphonate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 35.0h， 生成 (α-amino-4-fluorobenzyl)phosphonic acid
  参考文献：
  名称：

  Maier, Ludwig; Diel, Peter J., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 57, # 1/2, p. 57 - 64

  摘要：

  DOI：

文献信息

• Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates
  作者：P. P. Onys’ko、T. V. Kim、Yu. V. Rassukanaya、E. I. Kiseleva、A. D. Sinitsa

  DOI：10.1007/s11176-005-0007-6

  日期：2004.9

  Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N-C triad were revealed and applied in the synthesis of α-aminophosphonic acid derivatives.

  开发了合成方法以制备含有电子和立体多样的烷基取代基的苯并咪唑基磷酸酯衍生物，以及它们的质子化异构体。揭示了磷酸化C=N-C三元组中的质子转移规律，并应用于α-氨基磷酸衍生物的合成。
• THE PREPARATION AND CHARACTERIZATION OF SOME FLUORINATED α-AMINOARYLMETHANEPHOSPHONIC ACIDS
  作者：Donovan St. C. Green、Ulrike Gruss、Gerhard Hägele、Harry R. Hudson、Lars Lindblom、Max Pianka

  DOI：10.1080/10426509608046389

  日期：1996.6.1

  appear to have little effect on δH (15–18 ppm), or on the 1H and 13C parameters for the benzylic group (α-CH), which are mainly in the ranges observed for other types of α-aminoarylmethanephosphonic acids under alkaline conditions (δH, 3.8–4.0 ppm, 2 J PH 15.3–16.5 Hz; δc 57–58 ppm, 1 J PC 128–132 Hz). For those examples with fluorine in the ortho position (i.e., the 2-fluoro and pentafluoro derivatives)

  摘要 α-氨基芳基甲烷膦酸已在苯环（4-F、3-F、2-F、3,4-F2、F5、4-CF3、3- 、4- O 和 3- O)。这些化合物具有相对较低的水溶性，因此它们的 NMR 光谱（1H、13C、31P 和 19F）是在过量碱存在的 D2O 中记录的。在这些条件下，环取代基似乎对 δH (15–18 ppm) 或苄基 (α-CH) 的 1H 和 13C 参数几乎没有影响，这些参数主要在其他类型的 α 观察到的范围内-氨基芳基甲烷膦酸在碱性条件下（δH，3.8-4.0 ppm，2 J PH 15.3-16.5 Hz；δc 57-58 ppm，1 J PC 128-132 Hz）。对于邻位氟的那些例子（即，2-氟和五氟衍生物）观察到苄基碳原子（δc 50-51 ppm）的场化学位移略高。在快原子轰击质谱中，伪分子离子、MH+ 和离子导致...
• Substituted phosphonic analogues of phenylglycine as inhibitors of phenylalanine ammonia lyase from potatoes
  作者：Weronika Wanat、Michał Talma、Józef Hurek、Małgorzata Pawełczak、Paweł Kafarski

  DOI：10.1016/j.biochi.2018.06.005

  日期：2018.8

  A series of phosphonic acid analogues of phenylglycine variously substituted in phenyl ring have been synthesized and evaluated for their inhibitory activity towards potato l-phenylalanine ammonia lyase. Most of the compounds appeared to act as moderate (micromolar) inhibitors of the enzyme. Analysis of their binding performed using molecular modeling have shown that they might be bound either in active

  已经合成了一系列在苯环上被各种取代的苯基甘氨酸的膦酸类似物，并评估了它们对马铃薯1-苯基丙氨酸氨裂合酶的抑制活性。大多数化合物似乎充当该酶的中度（微摩尔）抑制剂。使用分子模型进行的结合分析表明，它们可能结合在酶的活性位点或非生理位点。后者位于邻近的深位点，靠近底物进入活性位点的进入通道。
• Inhibitors of phenylalanine ammonia-lyase: 1-aminobenzylphosphonic acids substituted in the benzene ring
  作者：Jerzy Zoń、Nikolaus Amrhein、Roman Gancarz

  DOI：10.1016/s0031-9422(01)00425-3

  日期：2002.1

  Dextrorotatory 1-amino-3',4'-dichlorobenzylphosphonic acid was found to be a potent inhibitor of the plant enzyme phenylalanine ammonia-lyase both in vitro and in vivo from among the ring-substituted 1-aminobenzylphosphonic acids and other analogues of phenylglycine. A structure activity relationship analysis of the results obtained permits predictions on the geometry of the pocket of the enzyme and is a basis in the strategy of better inhibitor synthesis. (C) 2002 Published by Elsevier Science Ltd.