膦酸,(氨基-2-噻嗯基甲基)-,二乙基酯 | 174737-65-6

• 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
• 中文名称: 膦酸,(氨基-2-噻嗯基甲基)-,二乙基酯
• 英文名称: diethyl (amino(thiophen-2- yl)methyl)phosphonate
• 英文别名: diethyl 1-amino(2-thienyl)methylphosphonate；Diethoxyphosphoryl(thiophen-2-yl)methanamine
• CAS: 174737-65-6
• 化学式: C₉H₁₆NO₃PS
• 分子量: 249.271
• InChiKey: YDUCEHMGEZECBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  膦酸,(氨基-2-噻嗯基甲基)-,二乙基酯 在 zinc dichromate trihydrate 作用下， 反应 0.17h， 以85%的产率得到diethyl thiophene-2-carbonylphosphonate
  参考文献：
  名称：

  室温下无​​溶剂条件下重铬酸锌三水合物 (ZnCr2O7˙3H2O) 氧化脱氨α-氨基膦酸酯和胺

  摘要：

  描述了一种使用 ZnCr 2 O 7 ·3H 2 O 在室温下无溶剂条件下通过氧化脱氨基快速有效地将多种 α-氨基膦酸酯转化为 α-酮膦酸酯的新方法。该方法也适用于各种类型的普通胺（伯胺和仲胺）以良好到高产率快速和高选择性氧化成醛和酮。

  DOI：

  10.1055/s-0029-1219174
• 作为产物：
  描述：

  diethyl thiophene-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 膦酸,(氨基-2-噻嗯基甲基)-,二乙基酯
  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

• 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
• Silica-Supported Ammonium Hydrogen Carbonate as an Efficient Reagent for One-Pot Synthesis of 1-Aminophosphonates from Aldehydes
  作者：Babak Kaboudin、Abbas Rahmani

  DOI：10.1055/s-2003-42427

  日期：——

  Silica-supported ammonium hydrogen carbonate was found to be an efficient reagent for the synthesis of 1-aminophosphonates under microwave irradiation in solvent-free conditions. This method is an easy, rapid, one-pot, and good-yielding reaction for the synthesis of 1-aminophosphonates.

  研究发现，在微波辐照和无溶剂条件下，二氧化硅支撑的碳酸氢铵是合成 1-氨基膦酸盐的高效试剂。该方法是合成 1-氨基膦酸盐的简便、快速、一锅反应且收率高的反应。
• Al(OTf)₃as an Efficient Catalyst for One-Pot Synthesis of Primary Diethyl 1-Aminophosphonates Under Solvent-Free Conditions
  作者：Sara Sobhani、Zahra Tashrifi

  DOI：10.1080/00397910802369695

  日期：2008.12.16

  A simple and general method has been developed for the one-pot, three-component synthesis of a variety of primary 1-aminophosphonates catalyzed by Al(OTf)(3) under solvent-free conditions in good to high yields.
• Molecular iodine: An efficient catalyst for the one-pot synthesis of primary 1-aminophosphonates
  作者：S. Sobhani、A. Vafaee

  DOI：10.1007/bf03245883

  日期：2010.3

  A new and convenient procedure has been developed for the one-pot synthesis of different types of primary 1-aminophosphonates from aldehydes/ketones, HMDS and diethyl phosphite using I-2 as an inexpensive, non-toxic, non-metallic and readily available catalyst. These reactions proceeded under solvent-free conditions and produced the desired products in high yields.