o-acetoxybenzyl acetate | 1575-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: o-acetoxybenzyl acetate
• 英文别名: 2-acetoxymethylphenyl acetate；diacetylsalicyl alcohol；2-(acetyloxy)benzyl acetate；Benzenemethanol,2-(acetyloxy)-,acetate；(2-acetyloxyphenyl)methyl acetate
• CAS: 1575-87-7
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: BXMVDJREQOBWDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  o-acetoxybenzyl acetate 在 氢溴酸 作用下， 生成 2-(溴甲基)乙酸苯酯
  参考文献：
  名称：

  Preparation of Acetoxybenzyl Bromides

  摘要：

  DOI：

  10.1021/jo01032a040
• 作为产物：
  描述：

  香豆素 在 吡啶 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 o-acetoxybenzyl acetate
  参考文献：
  名称：

  Stable Isotope Characterization of the ortho-Oxygenated Phenylpropanoids:  Coumarin and Melilotol

  摘要：

  The natural abundance H-2 NMR spectra of extractive coumarin 10 and of its dihydroderivative melilotol 11 produced by baker's yeast reduction has been compared with synthetic materials. Diagnostic for the differentiation of 10 are the (D/H)(beta) values, which are in the 128.1 -133.6 ppm interval for the natural compounds but 258.5 and 189.8 ppm for the synthetic materials. Such a dramatic difference is also found for methyl cinnamate 12, which shows (D/H)(beta) values of 127.2 and 515.8 ppm, respectively. In extractive 10, the ratio (D/H)(4(Para))/(D/H)(6(ortho)) = 1.24 is similar to that observed in structurally related salicin and methyl salicylate. Coumarin 10 is transformed in salicyl alcohol 9, providing diacetate 14, showing in the natural series the trend (D/H)(3(meta)) > (D/H)(4(para)) > (D/H)(5(meta)) similar to (D/H)(6(ortho)). A similar trend is shown also by the synthetic 10. A clear distinction between extractive and synthetic 10 is obtained through 6180 determinations on 10 and on chroman 13. The bulk delta O-18 values in the extractive series of 10 are 20.3, 23.6, and 22.6 parts per thousand, while those of the aromatic oxygen are 2.3, 0.5, and -0.5 parts per thousand. In the synthetic sample, the values are 12.6 and 5.6%., respectively. As a final product, the reduction of 10 leads to the dihydroderivative 11. Both the baker's yeast reduction and the catalytic hydrogenation lead to a marked decrease of the deuterium content of 11, which is stronger for the beta-position than for the alpha-position.

  DOI：

  10.1021/jf0518507

文献信息

• Acetylation of alcohols and phenols by zinc zirconium phosphate as an efficient heterogeneous catalyst under solvent-free conditions
  作者：Abdol Reza Hajipour、Hirbod Karimi、Morteza Karimzadeh

  DOI：10.1007/s00706-014-1222-9

  日期：2014.9

  AbstractAn efficient method for the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields under solvent-free conditions, using zinc zirconium phosphate as the catalyst was investigated. The catalyst was characterized by XRD, inductivity coupled plasma-optical emission spectroscopy, and scanning electron microscope. Products are easily isolated

  摘要在无溶剂条件下，以磷酸锌锆为催化剂，研究了一种有效的方法，可在无溶剂条件下以乙酸酐良好且优异的产率对多种醇和酚进行乙酰化。用XRD，电感耦合等离子体发射光谱和扫描电子显微镜对催化剂进行了表征。与现有方法相比，产品易于分离，并且操作流程温和绿色。 图形概要
• P₂O₅/Al₂O₃as an Efficient Heterogeneous Catalyst for the Acetylation of Alcohols, Phenols, Thiols, and Amines Under Solvent-Free Conditions
  作者：Amin Zarei、Abdol R. Hajipour、Leila Khazdooz

  DOI：10.1080/00397911.2010.492197

  日期：2011.5.4

  Abstract A convenient, rapid, and efficient method for the acetylation of alcohols, phenols, thiols, and amines has been developed by using acetic anhydride in the presence of a catalytic amount of P2O5 /Al2O3 under solvent-free conditions at room temperature. This reaction was studied under different conditions, and several solvents were examined for this conversion. However, in terms of reaction

  摘要 在室温无溶剂条件下，在催化量的 P2O5/Al2O3 存在下，使用乙酸酐开发了一种方便、快速、有效的乙酰化醇、酚、硫醇和胺的方法。在不同条件下研究了该反应，并针对该转化检查了几种溶剂。然而，在反应时间和收率方面，发现在无溶剂条件下进行反应时获得了最好的结果。没有观察到旋光醇的外消旋和糖的差向异构。采用无毒廉价的材料，后处理简单干净，反应时间短，产品收率好是该方法的优点。
• 4-Imidazol-1-yl-butane-1-sulfonic acid ionic liquid: Synthesis, structural analysis, physical properties and catalytic application as dual solvent-catalyst
  作者：Nader Ghaffari Khaligh、Taraneh Mihankhah、Mohd Rafie Johan、Joon Ching Juan

  DOI：10.1080/10426507.2018.1487426

  日期：2019.9.2

  Abstract 4-Imidazol-1-yl-butane-1-sulfonic acid (ImBu-SO3H) has been successfully synthetized and fully characterized by FT-IR and high-resolution NMR spectroscopy (1H, 13C). The “plausible” alternative structures of ImBu-SO3H were discussed on the basis of its NMR data. The ionic liquid showed interesting dual solvent-catalyst property, which was studied experimentally for the acetylation of a variety

  摘要 4-Imidazol-1-yl-butane-1-sulfonic acid (ImBu-SO3H) 已成功合成并通过 FT-IR 和高分辨率 NMR 光谱 (1H, 13C) 进行了充分表征。ImBu-SO3H 的“合理”替代结构在其 NMR 数据的基础上进行了讨论。离子液体显示出有趣的双溶剂-催化剂性质，实验研究了其乙酰化各种官能化的醇、酚、硫醇、胺和 α-生育酚 (α-CTP) 作为维生素 E 的最活性形式与乙酸酐并且在很短的反应时间内提供了良好的收率。ImBu-SO3H 通过产品萃取成功回收，随后 5 次运行的平均回收率为 82%。即使在连续五次运行后，回收的 ImBu-SO3H 的催化活性也几乎没有损失。图形概要
• Sulfamic Acid Catalysed Acetylation of Alcohols and Phenols with Acetic Anhydride
  作者：Tong-Shou Jin、Yan-Ran Ma、Zhan-Hui Zhang、Tong-Shuang Li

  DOI：10.1080/00397919808004417

  日期：1998.9

  Abstract An easy acetylation of alcohols and phenols with acetic anhydride has been carried out in excellent yield under catalysis of sulfamic acid.

  摘要 在氨基磺酸的催化下，醇和酚与乙酸酐的乙酰化反应以优异的收率进行。
• Brönsted Acidic Ionic Liquid as an Efficient Catalyst for Acetylation of Alcohols and Phenols
  作者：Abdol R. Hajipour、Leila Khazdooz、Arnold E. Ruoho

  DOI：10.1002/jccs.200900058

  日期：2009.4

  A novel Brönsted acidic room temperature ionic liquid (1‐H‐3‐methyl‐imidazolium bisulfate) is found to catalyze efficiently the acetylation of a wide rang of alcohols as well as phenols with acetic anhydride in good to excellent yields at 50°C under solvent‐free conditions. Products are easily isolated by extraction with ether and the protocol is mild and green, compared to the existing method based

  发现一种新型的Brönsted酸性室温室温离子液体（1-H-3-甲基咪唑鎓硫酸氢盐）在50°C的条件下于50°C时能有效催化各种醇和酚与乙酸酐的乙酰化无溶剂条件。与现有的基于有毒溶剂的方法相比，使用乙醚萃取可轻松分离出产品，操作方案温和绿色。