dimethyl (1-(4-chlorophenyl)-1-hydroxyethyl)phosphonate | 401610-08-0

• 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-(4-chlorophenyl)-1-hydroxyethyl)phosphonate
• 英文别名: dimethyl 1-(4-chlorophenyl)-1-hydroxyethylphosphonate；[1-(4-Chloro-phenyl)-1-hydroxy-ethyl]-phosphonic acid dimethyl ester；1-(4-chlorophenyl)-1-dimethoxyphosphorylethanol
• CAS: 401610-08-0
• 化学式: C₁₀H₁₄ClO₄P
• 分子量: 264.646
• InChiKey: GNZKCESBQQKZIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-Chloro-4-(1-dimethoxyphosphorylethyl)benzene 在 氧气 、 caesium carbonate 、 亚磷酸三乙酯 作用下， 以 二甲基亚砜 为溶剂， 以58%的产率得到dimethyl (1-(4-chlorophenyl)-1-hydroxyethyl)phosphonate
  参考文献：
  名称：

  通过膦酸酯化合物的直接羟基化反应合成α-羟基膦酸酯

  摘要：

  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。

  DOI：

  10.1002/cjoc.201400858

文献信息

• Reactions of acyl phosphonates with organoaluminum reagents: a new method for the synthesis of secondary and tertiary α-hydroxy phosphonates
  作者：Ozlem Seven、Sidika Polat-Cakir、Md. Shakhawoat Hossain、Mustafa Emrullahoglu、Ayhan S. Demir

  DOI：10.1016/j.tet.2011.03.036

  日期：2011.5

  ) with aryl and alkyl acyl phosphonates, which lead to the formation of α-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to secondary and tertiary α-hydroxy phosphonates depending on the reaction conditions. The reactions of triethylaluminum with a series of acyl phosphonates at 0 °C gave the secondary α-hydroxy phosphonates, while at −100 °C they afford

  报道了有机铝试剂（三甲基铝，三乙基铝等）与芳基和烷基酰基膦酸酯的反应，导致以中等至良好的产率形成α-羟基膦酸酯。根据反应条件，该方法可轻松获得仲和叔α-羟基膦酸酯。三乙基铝与一系列酰基膦酸酯在0°C的反应生成仲α-羟基膦酸酯，而在-100°C时，它们生成叔α-羟基膦酸酯。
• The catalytic aerobic synthesis of quaternary α-hydroxy phosphonates via direct hydroxylation of phosphonate compounds
  作者：Lijun Gu、Cheng Jin、Hongtao Zhang

  DOI：10.1039/c4nj02072c

  日期：——

  A highly efficient Cu-catalyzed direct hydroxylation of phosphonate compounds has been developed. This transformation provides a powerful method for the synthesis of quaternary α-hydroxy phosphonates in good yields. The direct transformation process, regiospecific selectivity, and good tolerance to a variety of substituents make it an alternative approach to the reported protocols.

  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。
• 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.
• C–H Hydroxylation of Phosphonates with Oxygen in [bmIm]OH To Produce Quaternary α-Hydroxy Phosphonates
  作者：Xiangguang Li、Cheng Jin、Lijun Gu

  DOI：10.1021/jo502883q

  日期：2015.2.20

  A highly efficient and mild [bmIm]OH-catalyzed a-hydroxylation of phosphonates using O-2 as the oxygen source is described. The employment of ionic liquid under mild reaction conditions makes this transformation green and practical. Especially, this reaction provided a novel and convenient methodology for the construction of quaternary a-hydroxy phosphonates.