diethyl (hydroxy(4-isopropylphenyl)methyl)phosphonate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl (hydroxy(4-isopropylphenyl)methyl)phosphonate
• 英文别名: Diethoxyphosphoryl-(4-propan-2-ylphenyl)methanol
• 化学式: C₁₄H₂₃O₄P
• 分子量: 286.308
• InChiKey: MMDUNVCXZPWUAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (hydroxy(4-isopropylphenyl)methyl)phosphonate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氨基磺酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 diethyl (4-isopropylbenzoyl)phosphonate
  参考文献：
  名称：

  A convenient and mild protocol for preparation of α –trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide

  摘要：

  DOI：

  10.24820/ark.5550190.p011.603
• 作为产物：
  描述：

  diethyl α-trimethylsilyloxy-4-isopropylbenzylphosphonate 在 氨基磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以89%的产率得到diethyl (hydroxy(4-isopropylphenyl)methyl)phosphonate
  参考文献：
  名称：

  A convenient and mild protocol for preparation of α –trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide

  摘要：

  DOI：

  10.24820/ark.5550190.p011.603

文献信息

• Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst
  作者：Makarand A. Kulkarni、Uday P. Lad、Uday V. Desai、Satish D. Mitragotri、Prakash P. Wadgaonkar

  DOI：10.1016/j.crci.2012.10.009

  日期：2013.2

  Résumé An extremely simple, high yielding, highly rapid and solvent-free protocol has been described for hydrophosphylation of aldehydes using potassium phosphate as catalyst. Easy commercial availability of the reusable catalyst, operational simplicity at ambient temperature and avoidance of conventional work-up as well as purification procedure makes this solvent-free protocol a near-ideal synthesis. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.pdf

  摘要 描述了一种极其简单、高产量、高速且无溶剂的醛类羟基磷化方法，使用磷酸钾作为催化剂。该可重复使用的催化剂易于商业获取，在常温下操作简单，并且避免了传统的后处理和纯化过程，使该无溶剂方案成为一种近乎理想的合成方法。 补充材料： 本文的补充材料以单独文件形式提供：mmc1.pdf
• Highly efficient green synthesis of α-hydroxyphosphonates using a recyclable choline hydroxide catalyst
  作者：Reddi Mohan Naidu Kalla、Yu Zhang、Il Kim

  DOI：10.1039/c6nj03948k

  日期：——

  Choline hydroxide has been found to be an efficient basic ionic liquid catalyst for the synthesis of α-hydroxyphosphonates. Hydrophosphonylation of aldehydes was performed via the nucleophilic addition of diethylphosphite to aldehydic carbonyl compounds, in the presence of choline hydroxide under neat as well as solvent conditions. A wide array of substrates, including aromatic, fused aromatic, and

  已经发现氢氧化胆碱是用于合成α-羟基膦酸酯的有效碱性离子液体催化剂。醛的氢膦酰化反应是通过在纯净和溶剂条件下在氢氧化胆碱存在下，将亚磷酸二乙酯亲核加成到醛基羰基化合物上进行的。包括芳香族，稠合芳香族和杂环醛在内的各种底物均以良好的收率有效地转化为其相应的产物。该方案为高产率直接合成α-羟基膦酸酯提供了另一种方法。
• Neat Synthesis and Anti-oxidant Activity of α-Hydroxyphosphonates
  作者：K. Uma Maheswara Rao、Ch. Syama Sundar、S. Siva Prasad、C. Radha Rani、C. Suresh Reddy

  DOI：10.5012/bkcs.2011.32.9.3343

  日期：2011.9.20

  reactions can produce free radicals duringmetabolism, which start chain reactions and damage cells.Antioxidants terminate these chain reactions by removingfree radical intermediates, and also inhibit other oxidationreactions. In recent years, a detailed mechanism of the antioxidantaction of organophosphorus compounds and their relation-ships between chemical structure and antioxidant activityhas been comprehensively

  , 抗氧化活性 介绍氧化反应会在新陈代谢过程中产生自由基，从而引发连锁反应并损害细胞。抗氧化剂通过去除自由基中间体来终止这些连锁反应，同时也抑制其他氧化反应。近年来，对有机磷化合物抗氧化作用的详细机制及其化学结构与抗氧化活性的关系进行了全面研究。亚磷酸盐和膦酸盐取决于它们的结构，既可以作为一级抗氧化剂，也可以作为二级抗氧化剂。
• Synthesis of α-Hydroxyphosphonates and Their Antioxidant Properties
  作者：Kalla Reddi Mohan Naidu、Krishnammagari Suresh Kumar、Palanisamy Arulselvan、Chinnappareddy Bhupendra Reddy、Ola Lasekan

  DOI：10.1002/ardp.201200192

  日期：2012.12

  synthesized from the reaction of aldehyde (1) with triethylphosphite (2) in the presence of oxone and evaluated for their antioxidant properties against lipid peroxidation, reduced glutathione, superoxide dismutase, and catalase. The majority of the compounds showed promising antioxidant activity. Diethyl anthracen‐9‐yl (hydroxy) methylphosphonate (3n) is the most potent and biologically active compound

  在 oxone 存在下，醛 (1) 与亚磷酸三乙酯 (2) 反应合成了一系列 α-羟基膦酸酯，并评估了它们对脂质过氧化、还原型谷胱甘肽、超氧化物歧化酶和过氧化氢酶的抗氧化性能。大多数化合物显示出有希望的抗氧化活性。二乙基蒽-9-基（羟基）甲基膦酸酯（3n）是对抗自由基最有效和生物活性的化合物。
• Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane
  作者：Ravindra V. Kupwade、Satish D. Mitragotri、Makarand A. Kulkarni、Uday V. Desai、Prakash P. Wadagaonkar

  DOI：10.24820/ark.5550190.p011.213

  日期：——