diethyl 2-(dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate | 150993-41-2

• 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: diethyl 2-(dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate
• 英文别名: diethyl ((1R,2S)-2-(dibenzylamino)-1-hydroxy-3-phenylpropyl)phosphonate；diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropyl-phosphonate；(1R,2S)-2-(dibenzylamino)-1-diethoxyphosphoryl-3-phenylpropan-1-ol
• CAS: 150993-41-2
• 化学式: C₂₇H₃₄NO₄P
• 分子量: 467.545
• InChiKey: ITQKBZQCDFEVAS-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate 在 palladium dihydroxide N-甲基吗啉 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 ((4S,5R)-4-Benzyl-2-oxo-oxazolidin-5-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Stereodivergent synthesis of β-amino-α-hydroxyphosphonic acid derivatives by lewis acid mediated stereosclective hydrophosphonylation of α-amino aldehydes

  摘要：

  The highly diastereoselective synthesis of beta-amino-alpha-hydroxyphosphonic acid derivatives was achieved by Lewis acid mediated hydrophosphonylation of alpha-dibenzylamino aldehyde. Diastereofacial differentiation could be controlled in either a chelation or a nonchelation manner by simple tuning of the nature of phosphoric nucleophiles.

  DOI：

  10.1016/s0957-4166(00)80325-0
• 作为产物：
  描述：

  [(1R,2S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-3-phenyl-propyl]-phosphonic acid diethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 diethyl 2-(dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate
  参考文献：
  名称：

  Stereodivergent synthesis of β-amino-α-hydroxyphosphonic acid derivatives by lewis acid mediated stereosclective hydrophosphonylation of α-amino aldehydes

  摘要：

  The highly diastereoselective synthesis of beta-amino-alpha-hydroxyphosphonic acid derivatives was achieved by Lewis acid mediated hydrophosphonylation of alpha-dibenzylamino aldehyde. Diastereofacial differentiation could be controlled in either a chelation or a nonchelation manner by simple tuning of the nature of phosphoric nucleophiles.

  DOI：

  10.1016/s0957-4166(00)80325-0

文献信息

• Application of α-Amino-β-fluorophosphonates in Construction of their Dipeptide Analogues
  作者：Marcin Kaźmierczak、Grzegorz Dutkiewicz、Tomasz Cytlak

  DOI：10.1055/s-0040-1707813

  日期：2020.8

  α-hydroxy-β-aminophosphonates. The reaction proceeds through an aziridinium ion formation, which was confirmed by the formation­ of a hexacoordinate phosphorus compound. Moreover, the absolute configuration of the obtained compounds was determined by X-ray analysis, which proved the stereochemistry.

  在本文中，我们目前在构建α-氨基-β-氟代膦酸酯的二肽类似物中的应用。在XtalFluor-E介导的α-羟基-β-氨基膦酸酯的脱氧氟化中制备了α-氨基-β-氟膦酸酯。该反应通过形成叠氮鎓离子而进行，这通过六配位磷化合物的形成得以证实。此外，通过X射线分析确定了所得化合物的绝对构型，证明了立体化学。
• Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates
  作者：Marcin Kaźmierczak、Henryk Koroniak

  DOI：10.3762/bjoc.16.69

  日期：——

  Herein, we present an efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates. Each step of the synthesis was optimized to provide excellent yields. Moreover, the absolute configuration of the obtained compounds was determined by X-ray analysis, which proved the stereochemistry that was proposed based on NMR studies.

  在本文中，我们提出了α-氟化β-氨基膦酸酯的二肽类似物的有效合成。优化了合成的每个步骤，以提供优异的收率。此外，通过X射线分析确定了所得化合物的绝对构型，这证明了基于NMR研究提出的立体化学。
• <i>A</i>- and<i>B</i>-fluorinated aminophosphonates–Synthesis and properties
  作者：Marcin Kaźmierczak、Maciej Kubicki、Henryk Koroniak

  DOI：10.1080/10426507.2015.1091832

  日期：2016.3.3

  GRAPHICAL ABSTRACT ABSTRACT Interest in synthesis of fluorinated aminophosphonates has grown significantly in recent years due to their promising applications in medicinal and bioorganic chemistry. We report herein efficient and general methods for the synthesis of α- and β-monofluorinated aminophosphonates. Series of β-fluoro aminophosphonates were prepared in nucleophilic DAST-mediated fluorination

  图形摘要 摘要 近年来，由于氟化氨基膦酸酯在药物和生物有机化学中的应用前景，人们对它们合成的兴趣显着增长。我们在此报告了合成 α- 和 β- 单氟化氨基膦酸酯的有效和通用方法。在亲核 DAST 介导的 α-羟基膦酸酯氟化中制备了一系列 β-氟氨基膦酸酯。含有氨基的羰基化合物与锂化的氟亚甲基二膦酸四乙酯之间的 Horner-Wadsworth-Emmons 反应用于合成 α-氟化-γ-氨基膦酸酯。此外，该协议有效地应用于二肽类似物α-氟化-γ-氨基膦酸盐的合成。
• Regioselective Fluorination of α-Hydroxy-β-aminophosphonates by Using PyFluor
  作者：Marcin Kaźmierczak、Maciej Kubicki、Henryk Koroniak

  DOI：10.1002/ejoc.201800631

  日期：2018.8.1

  the synthesis of α‐fluoro‐β‐aminophosphonates by the regioselective fluorination of α‐hydroxy‐β‐aminophosphonates under mild conditions. The fluorination reactions were mediated by the PyFluor reagent and occurred with the retention of configuration. The main products of this reaction were a series of α‐fluoro‐β‐aminophosphonates, which can be used as precursors in the preparation of medicinally important

  我们报告了在温和条件下通过α-羟基-β-氨基膦酸酯区域选择性氟化合成α-氟-β-氨基膦酸酯的简单协议。氟化反应是由PyFluor试剂介导的，并且在保留构型的情况下发生。该反应的主要产物是一系列的α-氟-β-氨基膦酸酯，可以用作制备具有医学重要性的化合物（例如二肽类似物）的前体。
• Towards Convenient Precursors for α -Phosphonylated Aziridinium Ions
  作者：Dorota G. Piotrowska、Andrzej E. Wróblewski

  DOI：10.1080/10426500902719867

  日期：2009.4.7

  mesylation of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-methylbutylphosphonate and diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate with mesyl chloride in the presence of tetraethylammonium chloride. These mixtures are considered as useful precursors to α -phosphonylated aziridinium ions.

  在将二甲基 (1R,2S)-2-(N,N) 甲磺酸化后，获得了相应的 2-(N,N-二苄基氨基)-1-氯-和 1-(N,N-二苄基氨基)-2-氯膦酸酯的混合物-二苄基氨基)-1-羟基-3-甲基丁基膦酸酯和二乙基(1R,2S)-2-(N,N-二苄基氨基)-1-羟基-3-苯基丙基膦酸酯与甲磺酰氯在四乙基氯化铵存在下。这些混合物被认为是 α-膦酰化氮丙啶离子的有用前体。