3-Acetoxy-1-(diacetoxymethyl)benzene | 6339-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-Acetoxy-1-(diacetoxymethyl)benzene
• 英文别名: 3-acetoxybenzylidene diacetate；1-acetoxy-3-diacetoxymethyl-benzene；1-Acetoxy-3-diacetoxymethyl-benzol；[3-(acetyloxy)phenyl]-methanediol, diacetate；[3-(Diacetyloxymethyl)phenyl] acetate
• CAS: 6339-75-9
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: BZDJVNWRYNELMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Acetoxy-1-(diacetoxymethyl)benzene 在 poly(4-vinylpyridinium) hydrogen sulfate solid acid 作用下， 以 甲醇 为溶剂， 反应 0.63h， 以82%的产率得到间羟基苯甲醛
  参考文献：
  名称：

  Ultrasound assisted the chemoselective 1,1-diacetate protection and deprotection of aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate salt as a eco-benign, efficient and reusable solid acid catalyst

  摘要：

  Poly(4-vinylpyridinium) hydrogen sulfate solid acid was found to be efficient catalyst for preparation of 1,1-diacetate using ultrasound irradiation at ambient temperature and neat condition. Deprotection of the resulting 1,1-diacetates were achieved using the same catalyst in methanol solvent under ultrasound irradiation at room temperature. This new method consistently has the advantage of excellent yields and short reaction times. Utilization of solvent free, simple reaction conditions, isolation, and purification makes this manipulation very interesting from an economic and environmental perspective. Further, the catalyst can be reused and recovered for several times. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2012.07.016
• 作为产物：
  描述：

  间硝基苯甲醛 在 盐酸 、 tin(ll) chloride 作用下， 生成 3-Acetoxy-1-(diacetoxymethyl)benzene
  参考文献：
  名称：

  Tiemann; Ludwig, Chemische Berichte, 1882, vol. 15, p. 2047

  摘要：

  DOI：

文献信息

• Silica-bonded S-sulfonic acid as a recyclable catalyst for chemoselective synthesis of 1,1-diacetates
  作者：Khodabakhsh Niknam、Dariush Saberi、Maryam Nouri Sefat

  DOI：10.1016/j.tetlet.2009.04.096

  日期：2009.7

  A simple and efficient procedure for the preparation of silica-bonded S-sulfonic acid (SBSSA) by reaction of 3-mercaptopropylsilica (MPS) and chlorosulfonic acid in chloroform is described. This solid acid is employed as a recyclable catalyst for the synthesis of 1,1-diacetates from aromatic aldehydes and acetic anhydride under mild and solvent-free conditions at room temperature.

  描述了一种通过3-巯基丙基二氧化硅（MPS）和氯磺酸在氯仿中反应制备二氧化硅键合的S-磺酸（SBSSA）的简单有效的方法。该固体酸被用作可循环利用的催化剂，用于在室温和无溶剂条件下由芳族醛和乙酸酐合成1,1-二乙酸酯。
• SiO2@FeSO4 NANO COMPOSITE AS NANOCATALYST FOR THE GREEN SYNTHESIS 1,1-DIACETATES FROM ALDEHYDES UNDER SOLVENT-FREE CONDITIONS
  作者：MOSTAFA KARIMKOSHTEH、MARZIYEH BAGHERI、BEHZAD ZEYNIZADEH

  DOI：10.4067/s0717-97072016000100007

  日期：——

  acetic anhydride (Ac 2 O) as acetylation reagent. This method provides several advantages, such as low cost of the nano catalyst, high yields, short reaction time, chemoselective protection of aldehydes and operational simplicity. Aromatic and aliphatic, simple and conjugated aldehydes were protected with excellent yields. In addition, chemoselective reductive acetylation of aldehydes over ketones was

  在室温，无溶剂条件下，以SiO 2 @FeSO 4纳米复合材料为有效的纳米催化剂，将乙醛化合物选择性转化为1,1-二乙酸酯作为保护剂，并在无溶剂条件下用乙酸酐（Ac 2 O）作为乙酰化剂。该方法具有许多优点，例如纳米催化剂的低成本，高收率，短的反应时间，醛的化学选择性保护和操作简便。芳香族和脂肪族，简单和共轭醛均得到了优异的保护。另外，在室温下用该试剂可以完美地实现醛在酮上的化学选择性还原乙酰化。方案1.由醛合成1，1-二乙酸酯。
• Sulphated Zirconia as an Eco-Friendly Catalyst in Acylal Preparation under Solvent-Free Conditions, Acylal Deprotection Assisted by Microwaves, and the Synthesis of Anhydro-Dimers of o-Hydroxybenzaldehydes
  作者：Laura Palacios-Grijalva、Deysi Cruz-González、Leticia Lomas-Romero、Eduardo González-Zamora、Gerardo Ulibarri、Guillermo Negrón-Silva

  DOI：10.3390/molecules14104065

  日期：——

  A solvent-free approach is described for the regioselective synthesis of acylals (1,1-diacetates) in shorter reaction times and higher yields, compared to conventional methodology using solvents. In the protection reaction of the o-hydroxybenzaldehyde the formation of acetyl compounds and anhydro-dimers was observed. The deprotection reaction involves microwave (MW) exposure of diluted reactants in

  与使用溶剂的传统方法相比，无溶剂方法可在更短的反应时间和更高的产率下区域选择性地合成酰基化合物（1,1-二乙酸酯）。在邻羟基苯甲醛的保护反应中，观察到乙酰化合物和脱水二聚体的形成。脱保护反应涉及稀释的反应物在固体硫酸化氧化锆 (SZ) 催化剂存在下的微波 (MW) 暴露，该催化剂可以轻松回收和重复使用。硫酸化氧化锆被回收多次而没有任何活性损失。
• Liquid-phase reactions of isomeric methylphenols with ozone
  作者：A. G. Galstyan

  DOI：10.1134/s1070363210010020

  日期：2010.1

  methylphenols in acetic anhydride was studied. Here, acetic anhydride acts simultaneously as solvent and acylating agent. In the presence of a mineral acid methylphenols were converted into methylphenyl acetates during preparation of solutions for ozonation. The major products in the oxidation of isomeric methylphenyl acetates with ozone were aliphatic peroxides (80–90%); oxidation of the methyl group gave

  研究了乙酸酐中异构甲基苯酚的臭氧化作用。在此，乙酸酐同时充当溶剂和酰化剂。在无机酸存在下，在制备用于臭氧化的溶液的过程中，甲基苯酚被转化为乙酸甲基苯酯。异构体乙酸甲基苯酯与臭氧的氧化反应主要产物为脂肪族过氧化物（80-90％）。甲基的氧化产生相应的乙酰氧基苄基乙酸酯（7–14％）和乙酰氧基苄基二乙酸酯（3–6％）。提出了在乙酸酐中用臭氧将乙酸甲基苯酯与臭氧液相氧化的可行方案。
• Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells–Dawson acid (H6P2W18O62·24H2O)
  作者：Gustavo P. Romanelli、Horacio J. Thomas、Graciela T. Baronetti、Juan C. Autino

  DOI：10.1016/s0040-4039(02)02817-4

  日期：2003.2

  Aromatic and aliphatic aldehydes are transformed in 1,1-diacetates (acylals) in mild conditions, by a treatment with acetic anhydride and a Wells–Dawson acid (H6P2W18O62·24H2O). gem-Diacetylation proceeds in Ac2O with a little as 1% mol Wells–Dawson acid at room temperature and under solventless conditions, obtaining very good to excellent yields (88–98%) of 1,1-diacetates (19 examples). Neither 4

  通过用乙酸酐和韦尔斯道森酸（H 6 P 2 W 18 O 62 ·24H 2 O）处理，可以在温和的条件下将芳香族和脂肪族醛转化为1,1-二乙酸酯（酰基）。在室温和无溶剂条件下，用少量的1％mol Wells-Dawson酸在Ac 2 O中进行宝石二乙酰化反应，获得1,1-二乙酸酯的非常好至极好的收率（88-98％）（19个实例）。4-二甲基氨基苯甲醛和酮都不会在相同条件下反应。