(2,4-Dichloro-benzoyl)-phosphonic acid diethyl ester | 255377-90-3

• 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: (2,4-Dichloro-benzoyl)-phosphonic acid diethyl ester
• 英文别名: Diethyl (2,4-dichlorobenzoyl)phosphonate；(2,4-dichlorophenyl)-diethoxyphosphorylmethanone
• CAS: 255377-90-3
• 化学式: C₁₁H₁₃Cl₂O₄P
• 分子量: 311.102
• InChiKey: LFLLBPWHWUMURC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,4-Dichloro-benzoyl)-phosphonic acid diethyl ester 在 sodium tetrahydroborate 、 盐酸羟胺 、 methyloxirane 、 molybdenum(VI) oxide 作用下， 以 吡啶 、 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 [氨基-(2,4-二氯苯基)甲基]膦酸
  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：

  (2,4-二氯苯基)-二乙氧基磷酰-甲醇 在 chromium(VI) oxide 、 aluminum oxide 作用下， 反应 8.0h， 以80%的产率得到(2,4-Dichloro-benzoyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Surface-mediated solid-phase reactions: the preparation of acyl phosphonates by oxidation of 1-hydroxyphosphonates on the solid surface

  摘要：

  Alumina-supported CrO3, under solvent-free conditions, was found to be an efficient oxidizing reagent for the preparation of acyl phosphonates from 1-hydroxyphosphonates. This method is an easy, rapid, and high-yielding reaction for the preparation of acyl phosphonates from 1-hydroxyphosphonates. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00323-3

文献信息

• Visible-light-induced coupling of carboxylic acids with alcohols/amines via a phosphorous linchpin strategy
  作者：Qiupeng Peng、Achyut Ranjan Gogoi、Ángel Rentería-Gómez、Osvaldo Gutierrez、Karl A. Scheidt

  DOI：10.1016/j.chempr.2023.04.011

  日期：2023.7

  organic chemistry and has been well developed over the past century. These dehydrations are extensively used in medicinal chemistry and natural product synthesis due to the prevalence of these functional groups in bioactive molecules. Here, we report a divergent process from the expected ester/amide outcomes through a light-induced coupling of activated carboxylic acids and alcohols/amines to efficiently

  活化的羧酸和醇/胺的组合分别形成酯和酰胺，是有机化学的基石，并且在过去的一个世纪中得到了很好的发展。由于这些官能团在生物活性分子中的普遍存在，这些脱水被广泛用于药物化学和天然产物合成。在这里，我们报告了一种与预期的酯/酰胺结果不同的过程，通过光诱导活化的羧酸和醇/胺的偶联，通过单电子化学有效地制备α-羟基/氨基酮或β-酮膦酸酯。磷关键策略允许通过分子内三重态自由基过程组合这些简单的试剂，从而形成新的碳-碳键。
• Surface-mediated solid-phase reactions: the preparation of acyl phosphonates by oxidation of 1-hydroxyphosphonates on the solid surface
  作者：Babak Kaboudin

  DOI：10.1016/s0040-4039(00)00323-3

  日期：2000.4

  Alumina-supported CrO3, under solvent-free conditions, was found to be an efficient oxidizing reagent for the preparation of acyl phosphonates from 1-hydroxyphosphonates. This method is an easy, rapid, and high-yielding reaction for the preparation of acyl phosphonates from 1-hydroxyphosphonates. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
  作者：Ayhan S. Demir、Cihangir Tanyeli、Özge Şeşenoǧlu、Şerafettin Demiç、Özden Özel Evin

  DOI：10.1016/0040-4039(95)02171-x

  日期：1996.1

  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.
• A CONVENIENT AND MILD PROCEDURE FOR THE PREPARATION OF α-KETO PHOSPHONATES OF 1-HYDROXYPHOSPHONATES UNDER SOLVENT-FREE CONDITIONS USING MICROWAVE
  作者：Babak Kaboudin、Rahman Nazari

  DOI：10.1081/scc-100104822

  日期：2001.1

  The Reactions of 1-hydroxyphosphonates on the alumina-supported CrO3 are accelerated by microwave irradiation under solvent-free conditions to afford a high yielding synthesis of alpha -keto phosphonates.