3-甲氧基苯基甲基磷酸氢盐 | 229982-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-甲氧基苯基甲基磷酸氢盐
• 英文名称: 3-methoxyphenyl methyl hydrogen phosphate
• 英文别名: 3-methoxyphenyl methyl hydrogenphosphate；methyl 3-methoxyphenyl phosphate；(3-Methoxyphenyl) methyl hydrogen phosphate；(3-methoxyphenyl) methyl hydrogen phosphate
• CAS: 229982-83-6
• 化学式: C₈H₁₁O₅P
• 分子量: 218.146
• InChiKey: SPWROUSGUDAHQP-UHFFFAOYSA-N

物化性质

• 沸点：
  327.2±44.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-甲氧基苯基甲基磷酸氢盐 在 palladium(II) trifluoroacetate 、 三甲基硅烷化重氮甲烷 作用下， 以 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 15.5h， 生成 4-methoxy[1,1'-biphenyl]-2-yl dimethyl phosphate
  参考文献：
  名称：

  Pd(II)-Catalyzed ortho-Arylation of Aryl Phosphates and Aryl Hydrogen Phosphates with Diaryliodonium Triflates

  摘要：

  Functionalized biaryl compounds were successfully synthesized using phosphates as the ortho-directing group in the Pd(II)Pd(IV) catalytic cycle.

  DOI：

  10.1021/ol400732q
• 作为产物：
  描述：

  3-甲氧基苯酚 在 吡啶 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 1.0h， 生成 3-甲氧基苯基甲基磷酸氢盐
  参考文献：
  名称：

  使用新的单磷酸直接基团，钯催化芳基氢磷酸的邻链烯基化。

  摘要：

  首次报道了使用单磷酸定向基团的高效Pd催化的邻链烯基化反应。该磷酸导向基团已成功用于各种烯基化产物的合成，并为过渡金属催化的CH活化提供了一种新方法。

  DOI：

  10.1039/c3cc41107a

文献信息

• A Simple DNase Model System Comprising a Dinuclear Zn(II) Complex in Methanol Accelerates the Cleavage of a Series of Methyl Aryl Phosphate Diesters by 10¹¹−10¹³
  作者：Alexei A. Neverov、C. Tony Liu、Shannon E. Bunn、David Edwards、Christopher J. White、Stephanie A. Melnychuk、R. Stan Brown

  DOI：10.1021/ja8006963

  日期：2008.5.1

  The di-Zn(II) complex of 1,3-bis[N-1,N-1'-(1,5,9-triazacyclododecyl)] propane with an associated methoxide (3:Zn(II)(2):-OCH3) was prepared and its catalysis of the methanolysis of a series of fourteen methyl aryl phosphate diesters (6) was studied at (s)(s)pH 9.8 in methanol at 25.0 +/- 0.1 degrees C. Plots of k(obs) VS [3:Zn(II)(2):-OCH3](free) for all members of 6 show saturation behavior from which K-M and k(cat)(max) were determined. The second order rate constants for the catalyzed reactions (k(cat)(max)/K-M) for each substrate are larger than the corresponding methoxide catalyzed reaction (k(2)(-OMe)) by 1.4 x 10(8) to 3 x 10(9)-fold. The values of kcatmax for all members of 6 are between 4 x 10(11) and 3 x 10(13) times larger than the solution reaction at (s)(s)pH 9.8, with the largest accelerations being given for substrates where the departing aryloxy unit contains ortho-NO2 or C(= O)OCH3 groups. Based on the linear Bronsted plots of k(cat)(max) VS (s)(s)pK(a)of the phenol, beta(Ig) values of -0.57 and -0.34 are determined respectively for the catalyzed methanolysis of "regular' substrates that do not contain the ortho-NO2 or C(= O)OCH3 groups, and those substrates that do. The data are consistent with a two step mechanism for the catalyzed reaction with rate limiting formation of a catalyst-coordinated phosphorane intermediate, followed by fast loss of the aryloxy leaving group. A detailed energetics calculation indicates that the catalyst binds the transition state comprising [CH3O-:6]double dagger, giving a hypothetical [3:Zn(II)(2):CH3O-:6]double dagger complex, by -21.4 to -24.5 kcal/mol, with the strongest binding being for those substrates having the ortho-NO2 or C(= O)OCH3 groups.
• <i>ortho</i>-Acetoxylation of Phosphonic and Phosphoric Monoacids via Pd(II) Catalysis
  作者：Li Yan Chan、Xiangjian Meng、Sunggak Kim

  DOI：10.1021/jo4011188

  日期：2013.9.6

  A simple and efficient method is developed for Pd-catalyzed ortho-acetoxylation using organophosphates, namely, benzylic phosphonic and aryl phosphoric monoacids, as the directing group.