O,O'-diethyl-1-amino-2-furylmethylphosphonate | 169334-91-2

• 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: O,O'-diethyl-1-amino-2-furylmethylphosphonate
• 英文别名: diethyl (amino(furan-2-yl)methyl)phosphonate；diethyl 1-amino(2-furyl)methylphosphonate；[Diethoxyphosphoryl-(furan-2-yl)-methyl]-amine；diethoxyphosphoryl(furan-2-yl)methanamine
• CAS: 169334-91-2
• 化学式: C₉H₁₆NO₄P
• 分子量: 233.204
• InChiKey: XGAWJTYLCBVCRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O,O'-diethyl-1-amino-2-furylmethylphosphonate 在 methyloxirane 作用下， 以 乙醇 为溶剂， 以85%的产率得到[amino(2-furyl)methyl]phosphonic acid
  参考文献：
  名称：

  A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

  摘要：

  A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroxyiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1- aminophosphonates gave 1-aminophosphonic acids in good yield.

  DOI：

  10.1016/0040-4039(95)02171-x
• 作为产物：
  描述：

  diethyl furan-2-carbonylphosphonate 在 sodium tetrahydroborate 、 盐酸羟胺 、 molybdenum(VI) oxide 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 6.0h， 生成 O,O'-diethyl-1-amino-2-furylmethylphosphonate
  参考文献：
  名称：

  A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

  摘要：

  A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroxyiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1- aminophosphonates gave 1-aminophosphonic acids in good yield.

  DOI：

  10.1016/0040-4039(95)02171-x

文献信息

• Surface-Mediated Solid Phase Reactions: A Simple and New Method for the Synthesis of<i>α</i>-Aminophosphonates under Solvent-Free Conditions
  作者：Babak Kaboudin

  DOI：10.1246/cl.2001.880

  日期：2001.9

  Alumina-supported ammonium formate was found to be an efficient reagent for the synthesis of 1-aminophosphonates from aldehydes and diethyl phosphite. This method is an easy, rapid and high-yieldin...

  发现氧化铝负载的甲酸铵是从醛和亚磷酸二乙酯合成 1-氨基膦酸酯的有效试剂。这种方法是一种简单、快速和高产...
• Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
  作者：Babak Kaboudin、Rahman Nazari

  DOI：10.1016/s0040-4039(01)01627-6

  日期：2001.11

  simple, efficient and general method has been developed for the synthesis of 1-aminoalkyl phosphonates through a one-pot reaction of aldehydes with amines in the presence of acidic alumina under solvent-free conditions using microwave irradiation. It was also found that acidic alumina supported ammonium formate under solvent-free conditions is capable of the synthesis of 1-aminophosphonates from aldehydes

  已经开发了一种简单，有效且通用的方法，该方法通过在无溶剂条件下使用微波辐射在酸性氧化铝存在下，醛与胺进行一锅反应来合成1-氨基烷基膦酸酯。还发现在无溶剂条件下酸性氧化铝负载的甲酸铵能够在温和的反应条件下由醛和亚磷酸二乙酯合成1-氨基膦酸酯。
• Rational Design of Potent Inhibitors of a Metallohydrolase Using a Fragment‐Based Approach
  作者：Daniel Feder、Siti H. Mohd‐Pahmi、Waleed M. Hussein、Luke W. Guddat、Ross P. McGeary、Gerhard Schenk

  DOI：10.1002/cmdc.202100486

  日期：2021.11.5

  mammalian PAP with bound fragment molecules inspired scaffolds for inhibitor design. Three novel scaffolds of phosphonate inhibitors were designed and docked to pig and human PAPs. The most potent inhibitor within this series has a Ki value of 300 nM against pig PAP. Additional noncovalent scaffolds provide avenues for the design of PAP inhibitors with novel modes of action.

  人紫色酸性磷酸酶(PAP) 与骨质疏松症有关。具有结合片段分子的哺乳动物 PAP 的高分辨率晶体结构启发了用于抑制剂设计的支架。设计了三种新型膦酸盐抑制剂支架并将其与猪和人类 PAP 对接。该系列中最有效的抑制剂对猪 PAP 的K i值为 300 nM。额外的非共价支架为设计具有新作用模式的 PAP 抑制剂提供了途径。
• One-pot synthesis of primary 1-aminophosphonates: Coupling reaction of carbonyl compounds, hexamethyldisilazane, and diethyl phosphite catalyzed by Al(OTf)₃
  作者：Sara Sobhani、Zahra Tashrifi

  DOI：10.1002/hc.20517

  日期：——

  Al(OTf)3 has been utilized as a new and efficient catalyst for the selective synthesis of primary 1-aminophosphonates by a one-pot coupling reaction of various types of aldehydes/ketones, hexamethyldisilazane, and diethyl phosphite under solvent-free conditions. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:109–115, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI

  Al(OTf)3 已被用作一种新型高效催化剂，通过各种醛/酮、六甲基二硅氮烷和亚磷酸二乙酯在无溶剂条件下的一锅偶联反应选择性合成伯 1-氨基膦酸酯。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:109–115, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20517
• One-Pot Synthesis of α-Aminophosphonates on Silica under Solvent-Free Conditions from Aromatic Aldehydes
  作者：Ming Shu Wu、Xiang Zhu Zhang

  DOI：10.3184/030823408x349998

  日期：2008.10

  α-Aminophosphonates were synthesised under solvent-free conditions on an acidic silica gel support using aromatic aldehydes, diethyl phosphite and anhydrous ammonium acetate as starting materials in moderate yields

  以芳香醛、亚磷酸二乙酯和无水醋酸铵为起始原料，在无溶剂条件下，在酸性硅胶载体上合成α-氨基膦酸酯，收率适中