1-amino-1-(1'-naphthyl)methanephosphonic acid | 18108-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-amino-1-(1'-naphthyl)methanephosphonic acid
• 英文别名: Aminonaphthyl-(1)-methanphosphonsaeure；[1-Amino-1-(1-naphthyl)methyl]phosphonic acid；[amino(naphthalen-1-yl)methyl]phosphonic acid
• CAS: 18108-25-3
• 化学式: C₁₁H₁₂NO₃P
• 分子量: 237.195
• InChiKey: ZROTTZYTQIGFFG-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270 °C(Solv: water (7732-18-5))
• 沸点：
  503.8±60.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(Acetylamino-naphthalen-1-yl-methyl)-acetamide 在 盐酸 、 溶剂黄146 、 三氯化磷 作用下， 生成 1-amino-1-(1'-naphthyl)methanephosphonic acid
  参考文献：
  名称：

  Soroka, Miroslaw; Jaworska, Dorota; Szczesny, Zbigniew, Liebigs Annalen der Chemie, 1990, # 11, p. 1153 - 1155

  摘要：

  DOI：

文献信息

• Extremely short H···H distances and intermolecular hydrogen-bonding patterns of dialkyl α-aryl-α-(diphenylmethylamino)methanephosphonates
  作者：Harry R. Hudson、Mátyás Czugler、Rosalind J. Lee、Thomas M. Woodroffe

  DOI：10.1080/10426507.2015.1091833

  日期：2016.3.3

  types of hydrogen bonding, leading to the formation of (a) dimers containing two molecules of the same stereochemistry (SS or RR) in one case, (b) centrosymmetric dimers containing two enantiomeric molecules (RS) (both involving P=O···H–N interactions) in two crystals, and (c) in the anthryl derivative, a short intramolecular C–H···O=P contact distance but no involvement of the amino N–H. The anthryl

  图形摘要摘要四种 N-二苯甲基保护的 α-氨基-α-芳基甲烷膦酸二乙酯（芳基 = 苯基、1-萘基、1-蒽基和 1-芘基）的单晶 X 射线衍射研究揭示了几种不同类型的氢键，导致 (a) 在一种情况下形成包含两个相同立体化学分子 (SS 或 RR) 的二聚体，(b) 包含两个对映体分子 (RS) 的中心对称二聚体（均涉及 P=O…H–N 相互作用) 在两个晶体中，和 (c) 在蒽基衍生物中，分子内 C–H…O=P 接触距离较短，但不涉及氨基 N–H。蒽基衍生物形成分子链，在磷酰氧和相邻分子中二苯甲基之一的苯基氢原子之间可能存在相互作用。这些分子采用 C-P 键的交错构象，手性 α-碳原子的 H 原子与 N-H 大致相反。另一个特点是 1-萘基、1-蒽基和 1-芘基部分的“肩”H 原子与手性 α-碳 H 原子的距离极短，比总和短约 0.4-0.6 Å。范德华半径。在 1-蒽基取代的晶体中，与 N-H
• 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.
• 1-AMINO-1-ARYL- AND 1-AMINO-1-HETEROARYL-METHANEPHOSPHONIC ACIDS AND THEIR<i>N</i>-BENZHYDRYL–PROTECTED DIETHYL ESTERS: PREPARATION AND CHARACTERIZATION
  作者：Harry R. Hudson、Rosalind J. Lee、Ray W. Matthews

  DOI：10.1080/10426500490466274

  日期：2004.9

  N-Benzhydryl-protected diethyl esters of 1-amino-1-aryl- (phenyl, cumyl, p-dimethylaminophenyl, piperonyl, 1'-naphthyl, 9'-anthryl, T-pyrenyl) and 1-ainino-1-heteroaryl- (furyl, 2'-thienyl, X-thienyl, 2'-pyrrolyl)-methanephosphonic acids, prepared by the addition of diethyl phosphite to the corresponding benzhydryl imines, have been isolated, purified, and characterized. The presence of chiral alpha-carbon and prochiral phosphorus in these esters gives rise to complicated features in their NMR spectra, which are discussed. Hydrolysis of the crude 1-aryl compounds in situ gave modest yields of the corresponding aminophosphonic acids (except for 1'-pyrenyl). Of the 1-heteroaryl derivatives, only the 2'-thienyl compound gave the expected aminophosphonic acid; in other cases, alternative modes of decomposition may occur under hydrolytic conditions. NMR and mass spectral data are given for all products.
• Darstellung von α-aminophosphonsäureestern und verwandten Verbindungen
  作者：Hellmut Hoffmann、Heinz Förster

  DOI：10.1007/bf00908943

  日期：1968.1
• SOROKA, MIROSLAW;JAWORSKA, DOROTA;SZCZESNY, ZBIGNIEW, LIEBIGS ANN. CHEM.,(1990) N1, C. 1153-1155
  作者：SOROKA, MIROSLAW、JAWORSKA, DOROTA、SZCZESNY, ZBIGNIEW

  DOI：——

  日期：——