dimethyl (1-hydroxy-1-(thiophen-2-yl)ethyl)phosphonate | 31166-76-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl (1-hydroxy-1-(thiophen-2-yl)ethyl)phosphonate
• 英文别名: dimethyl 1-hydroxy-1-(thiophen-2-yl)ethylphosphonate；1-[Dimethoxy(oxido)phosphaniumyl]-1-thiophen-2-ylethanol；1-[dimethoxy(oxido)phosphaniumyl]-1-thiophen-2-ylethanol
• CAS: 31166-76-4
• 化学式: C₈H₁₃O₄PS
• 分子量: 236.229
• InChiKey: VUNMCJNPFFZYOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  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56%的产率得到dimethyl (1-hydroxy-1-(thiophen-2-yl)ethyl)phosphonate
  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

• 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。
• Highly Efficient Synthesis of Quaternary α-Hydroxy Phosphonates<i>via</i>Lewis Acid-Catalyzed Hydrophosphonylation of Ketones
  作者：Xin Zhou、Yanling Liu、Lu Chang、Jiannan Zhao、Deju Shang、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1002/adsc.200900531

  日期：2009.11

  A Lewis acid catalyst has been first applied to the hydrophosphonylation of ketones, giving the corresponding quaternary α-hydroxy phosphonates in high yields (up to 98%). The present method was highly tolerable for functionalized ketones. Moreover, the first catalytic enantioselective hydrophosphonylation of an unactivated ketone was also realized by using a tridentate Schiff base-titanium complex

  路易斯酸催化剂已首先应用于酮的氢膦酰化反应，从而以高收率（高达98％）得到相应的季α-羟基膦酸酯。本方法对于官能化的酮具有高度的耐受性。此外，还通过使用三齿席夫碱-钛络合物实现了未活化的酮的第一催化对映体选择性氢膦酰基化。
• 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.
• 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。