[amino-(4-methoxyphenyl)methyl]phosphonic acid | 16656-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [amino-(4-methoxyphenyl)methyl]phosphonic acid
• 英文别名: (RS)-Amino(4-Methoxyphenyl)Methylphosphonic Acid
• CAS: 16656-61-4
• 化学式: C₈H₁₂NO₄P
• mdl: MFCD24388559
• 分子量: 217.161
• InChiKey: RPFVXHNHQIUDSG-UHFFFAOYSA-N

物化性质

• 熔点：
  215-218 °C
• 沸点：
  450.0±55.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [amino-(4-methoxyphenyl)methyl]phosphonic acid 生成 [[[(2S)-2-aminopropanoyl]amino]-(4-methoxyphenyl)methyl]phosphonic acid;trihydrate
  参考文献：
  名称：

  KAFARSKI, PAWEL;LEJCZAK, BARDARA;SLESAK, EDWARD;PRZETOCKI, JACEK, PESTIC. SCI., 25,(1989) N, C. 137-143

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基二氮苯甲醛 生成 [amino-(4-methoxyphenyl)methyl]phosphonic acid
  参考文献：
  名称：

  Rachon,J.; Wasielewski,C., Roczniki Chemii, 1975, vol. 49, p. 397 - 402

  摘要：

  DOI：

文献信息

• Synthesis and stability of 1-aminoalkylphosphonic acid quaternary ammonium salts
  作者：Anna Brol、Tomasz K. Olszewski

  DOI：10.1039/d1ob00703c

  日期：——

  convenient alkylating agent is reported. During the course of the reaction, phosphonic acid quaternary ammonium derivatives, along with their corresponding monoesters are formed. Subsequent direct acidic hydrolysis of the crude reaction mixture leads to the desired novel N,N,N-trialkyl-N-(1-phosphonoalkyl)ammonium salts with overall yields of up to 88%. The developed protocol is general in scope and the products

  报道了使用 Me 2 SO 4作为方便的烷基化剂在碱性条件下对简单的 1-氨基烷基膦酸进行季铵化的有效方案。在反应过程中，形成膦酸季铵衍生物及其相应的单酯。随后粗反应混合物的直接酸水解产生所需的新的N , N , N-三烷基-N-(1-膦酰基烷基)铵盐，总收率高达 88%。开发的方案在范围上是通用的，产品通过简单的结晶纯化，得到稳定的固体。带有膦基的新型季铵盐通常在酸性和碱性介质中不反应。然而，它们中的一些在碱的存在下会发生霍夫曼消除和取代反应。
• Synthesis of phosphinic and phosphonic analogs of aromatic amino acids
  作者：A. V. Belyankin、A. R. Khomutov、Yu. N. Zhukov、O. N. Kartasheva、R. M. Khomutov

  DOI：10.1007/bf02495362

  日期：1997.1

  The reaction of aryl and aralkyl aldoximes with hypophosphorous acid resulted in aminophosphinic acids, which were oxidized into the corresponding aminophosphonic acids.

  芳基和芳烷基醛肟与次磷酸反应生成氨基次膦酸，氨基次膦酸被氧化成相应的氨基膦酸。
• Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl)alkanimines with phosphorus trichloride in acetic acid or with phosphonic acid in acetic anhydride.
  作者：Miroslaw Soroka、Waldemar Goldeman

  DOI：10.3998/ark.5550190.0011.b29

  日期：——

  The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields.

  三氯化磷在乙酸中或在乙酸酐中的膦酸（亚磷酸）与 N-（三苯基甲基）链烷胺反应生成 1-乙酰氨基烷基膦酸 1a-j，水解后生成 1-氨基烷基膦酸 2a-j，收率良好。
• 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。
• 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。