dimethyl 2,4-dimethoxyphenyl phosphate | 94420-70-9

• 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 2,4-dimethoxyphenyl phosphate
• 英文别名: (2,4-dimethoxyphenyl) dimethyl phosphate
• CAS: 94420-70-9
• 化学式: C₁₀H₁₅O₆P
• 分子量: 262.199
• InChiKey: YTNCJBLNRQOUGW-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±42.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 dimethyl 2,4-dimethoxyphenyl phosphate 在 吡啶 、 cesium fluoride 作用下， 生成 2,4-二甲氧基苯基乙酸酯
  参考文献：
  名称：

  对苯甲醌与亚磷酸三烷基酯的磷酸化反应制备区域选择性保护的氢醌†

  摘要：

  该标题反应已应用于10个单取代的对苯醌（方案2，表）。O-磷酸化的区域选择性受大的取代基（叔丁基和三甲基甲硅烷基）的影响，并且电子上受甲氧基的影响。在非极性介质（苯）中的区域选择性高，在极性溶剂（CH 2 Cl 2）和（CH 3 CN）中较低。该转化的合成潜力，例如化合物29（方案3）和32（方案4）的制备），通过使用温和的方法进行磷酸盐水解并使用试剂对P（OCH 3）3 /三甲基甲硅烷基氯进行了相当大的扩展，这使对羟基苯基磷酸盐的清洁获取成为可能。具有强π受体取代基的对苯醌4th和4i以不同的方式反应，生成膦酸酯。O-磷酸化的电子诱导的区域选择性符合亲核磷酸化试剂的攻击预期的偏好。

  DOI：

  10.1002/hlca.19840670529
• 作为产物：
  描述：

  甲氧苯醌 、 三甲氧基磷 以 氘代氯仿 为溶剂， 以84.8%的产率得到dimethyl 2,4-dimethoxyphenyl phosphate
  参考文献：
  名称：

  Semiquantitative Determination of Quinonoid Structures in Isolated Lignins by ³¹P Nuclear Magnetic Resonance

  摘要：

  A semiquantitative analytical method has been developed for the determination of the total quinonoid content; (o-benzoquinones and p-benzoquinones) of soluble lignins. The method is based on detailed measurements and observations made with model o- and p-quinones, which in dry organic solvents were shown to form adducts with trimethyl phosphite in quantitative yield. These adducts gave P-31 NMR signals for o- and p-quinones at around -46 and -2 ppm, respectively. In the presence of moisture and lignin the adducts from o-quinones were shown to be hydrolyzed to the open ring product, dimethylphenyl phosphate (-2 ppm), at an overall yield of similar to 70%. Similarly, the hydrolysis yields of p-quinone adducts with trimethyl phosphite were similar to 70%. Consequently, a number of important issues in relation to the use of trimethyl phosphite toward the quantitative analysis of quinonoid groups in lignins have been investigated, which permitted the development of an experimental semiquantitative protocol recommended for spectral acquisition.

  DOI：

  10.1021/jf9804802

文献信息

• DUTHALER, R. O.;LYLE, P. A.;HEUBERGER, C., HELV. CHIM. ACTA, 1984, 67, N 5, 1406-1426
  作者：DUTHALER, R. O.、LYLE, P. A.、HEUBERGER, C.

  DOI：——

  日期：——
• Preparation of Regioselectively Protected Hydroquinones by Phosphorylation ofp-Benzoquinones with Trialkyl Phosphites
  作者：Rudolf O. Duthaler、Paulette A. Lyle、Christoph Heuberger

  DOI：10.1002/hlca.19840670529

  日期：1984.8.8

  methoxy group. The regioselectivity, which is high in nonpolar media (benzene), is lower in polar solvents (CH2Cl2) and (CH3CN). The synthetic potential of this transformation, exemplified by the preparation of compounds 29 (Scheme 3) and 32 (Scheme 4), is considerably extended by applying milder methods for the phosphate hydrolysis and by using the reagent couple P(OCH3)3/trimethylsilyl chloride, which

  该标题反应已应用于10个单取代的对苯醌（方案2，表）。O-磷酸化的区域选择性受大的取代基（叔丁基和三甲基甲硅烷基）的影响，并且电子上受甲氧基的影响。在非极性介质（苯）中的区域选择性高，在极性溶剂（CH 2 Cl 2）和（CH 3 CN）中较低。该转化的合成潜力，例如化合物29（方案3）和32（方案4）的制备），通过使用温和的方法进行磷酸盐水解并使用试剂对P（OCH 3）3 /三甲基甲硅烷基氯进行了相当大的扩展，这使对羟基苯基磷酸盐的清洁获取成为可能。具有强π受体取代基的对苯醌4th和4i以不同的方式反应，生成膦酸酯。O-磷酸化的电子诱导的区域选择性符合亲核磷酸化试剂的攻击预期的偏好。
• Semiquantitative Determination of Quinonoid Structures in Isolated Lignins by ³¹P Nuclear Magnetic Resonance
  作者：Dimitris S. Argyropoulos、Liming Zhang

  DOI：10.1021/jf9804802

  日期：1998.11.1

  A semiquantitative analytical method has been developed for the determination of the total quinonoid content; (o-benzoquinones and p-benzoquinones) of soluble lignins. The method is based on detailed measurements and observations made with model o- and p-quinones, which in dry organic solvents were shown to form adducts with trimethyl phosphite in quantitative yield. These adducts gave P-31 NMR signals for o- and p-quinones at around -46 and -2 ppm, respectively. In the presence of moisture and lignin the adducts from o-quinones were shown to be hydrolyzed to the open ring product, dimethylphenyl phosphate (-2 ppm), at an overall yield of similar to 70%. Similarly, the hydrolysis yields of p-quinone adducts with trimethyl phosphite were similar to 70%. Consequently, a number of important issues in relation to the use of trimethyl phosphite toward the quantitative analysis of quinonoid groups in lignins have been investigated, which permitted the development of an experimental semiquantitative protocol recommended for spectral acquisition.