dimethyl 1,1-diphenyl-1-hydroxymethylphosphonate | 34881-12-4

• 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: dimethyl 1,1-diphenyl-1-hydroxymethylphosphonate
• 英文别名: dimethyl (hydroxydiphenylmethyl)phosphonate；dimethyl hydroxydiphenylmethylphosphonate；(α-hydroxy-benzhydryl)-phosphonic acid dimethyl ester；(α-Hydroxy-benzhydryl)-phosphonsaeure-dimethylester；Dimethyl-1-hydroxy-1,1-diphenylmethylphosphonat；Dimethoxyphosphoryl(diphenyl)methanol
• CAS: 34881-12-4
• 化学式: C₁₅H₁₇O₄P
• 分子量: 292.271
• InChiKey: PQYBBQGNHPVZIT-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  445.7±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  dimethyl 1,1-diphenyl-1-hydroxymethylphosphonate 在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以94%的产率得到1,1-二苯基-1-羟甲基膦酸
  参考文献：
  名称：

  Inhibition of mandelate racemase by the substrate–intermediate–product analogue 1,1-diphenyl-1-hydroxymethylphosphonate

  摘要：

  Mandelate racemase has been studied as a paradigm for enzyme-catalyzed abstraction of a proton from carbon acids with relatively high pK(a) values. 1,1-Diphenyl-1-hydroxymethylphosphonate is a substrate-intermediate-product analogue and is a modest competitive inhibitor of the enzyme (K-i = 1.41 +/- 0.09 mM), suggesting that simultaneous binding of the two phenyl groups obviates mimicry of the aci-carboxylate function of the intermediate by the phosphonate group. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.060
• 作为产物：
  描述：

  [二甲氧基磷酰基(苯基)甲基]苯 在 N-羟基邻苯二甲酰亚胺 、 copper(II) choride dihydrate 、 氧气 、 三苯基膦 作用下， 以 乙腈 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以75%的产率得到dimethyl 1,1-diphenyl-1-hydroxymethylphosphonate
  参考文献：
  名称：

  通过膦酸酯化合物的直接羟基 化催化有氧合成季α-羟基膦酸酯†

  摘要：

  已经开发了高效的铜催化的膦酸酯化合物的直接羟基化。该转化为以高收率合成α-羟基膦酸酯季盐提供了一种有力的方法。直接转化过程，区域特异性选择性以及对各种取代基的良好耐受性使其成为所报道方案的替代方法。

  DOI：

  10.1039/c4nj02072c

文献信息

• Ultrasound assisted green synthesis of α-hydroxyphosphonates under solvent-free conditions
  作者：Abdeslem Bouzina、Nour-eddine Aouf、Malika Berredjem

  DOI：10.1007/s11164-015-2420-8

  日期：2016.6

  Abstract A simple, efficient and environmentally benign method for the synthesis of α-hydroxyphosphonates by reaction of an aldehyde or a ketone, and trialkylphosphite is effectively accomplished under ultrasound irradiation and solvent-free and catalyst-free conditions. This rapid method produces α-hydroxyphosphonates in high yields and short reaction times. Graphical Abstract

  摘要 通过醛或酮与亚磷酸三烷基酯的反应合成α-羟基膦酸酯的简单，有效，环境友好的方法在超声辐射，无溶剂和无催化剂的条件下有效地实现。这种快速的方法可以高产率和短反应时间生产α-羟基膦酸酯。 图形概要
• Synthesis of Quaternary<i>α</i>-Hydroxy Phosphonates<i>via</i>Direct Hydroxylation of Phosphonate Compounds
  作者：Jiyan Liu、Wei Wang、Rui Wang、Lijun Gu

  DOI：10.1002/cjoc.201400858

  日期：2015.5

  It was found for the first time that Cs2CO3 serves as highly efficient catalyst for the direct hydroxylation reactions of phosphonates under mild conditions. This reaction provides an efficient approach to quaternary α‐hydroxy phosphonates, which possess intriguing biological activities and are widely used in many areas.

  首次发现在温和条件下，Cs 2 CO 3可以用作膦酸酯直接羟基化反应的高效催化剂。该反应提供了一种有效的方法来处理季铵化的α-羟基膦酸酯，其具有令人着迷的生物学活性，并在许多领域得到了广泛的应用。
• Solvent-Free Synthesis of Tertiaryα-Hydroxyphosphates by the Triethylamine-Catalyzed Hydrophosphonylation of Ketones
  作者：Chubei Wang、Jianwei Zhou、Xingbin Lv、Junlei Wen、Hongwu He

  DOI：10.1080/10426507.2013.765874

  日期：2013.10.1

  A new, environmentally benign, convenient, and easy method of synthesizing tertiary -hydroxyphosphonates by the triethylamine-catalyzed hydrophosphonylation of unactivated ketones was developed. In the presence of triethylamine, aromatic or heteroaromatic ketones can react with phosphite to form tertiary -hydroxyphosphonates under solvent-free and mild conditions. The proposed method was also suitable for functionalized ketones.
• An unexpected reactivity of simple heterogeneous mixture of γ-alumina and potassium fluoride : 1-hydroxyalkane phosphonic esters synthesis from non-activated ketones in “dry media”.
  作者：Françoise Texier-Boullet、Maryvonne Lequitte

  DOI：10.1016/s0040-4039(00)84837-6

  日期：1986.1
• Shahak,I.; Peretz,J., Israel Journal of Chemistry, 1971, vol. 9, p. 35 - 44
  作者：Shahak,I.、Peretz,J.

  DOI：——

  日期：——