1,1-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)methane

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,1-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)methane
• 英文别名: acetyloxy(4-hydroxy-3-methoxyphenyl)methyl acetate；4-acetoxy-3-methoxybenzaldehyde-1,1-diacetate；[Acetyloxy-(4-hydroxy-3-methoxyphenyl)methyl] acetate
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: XRTLMMLATOFJTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)methane 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以91%的产率得到香草醛
  参考文献：
  名称：

  硝酸铈铵催化醛类化学选择性合成酰基醛及其脱保护的温和高效方法

  摘要：

  已经开发了一种温和有效的方法，用于在催化量的硝酸铈铵存在下使用乙酸酐从醛化学选择性合成双乙酸酯（酰基），收率极好。发现酮在反应条件下不受影响。还实现了用水和硝酸铈铵对酰基进行脱保护。

  DOI：

  10.1055/s-2002-34243
• 作为产物：
  描述：

  乙酸酐 、 香草醛 在 aluminum oxide 、 磷酸酐 作用下， 反应 2.5h， 以80%的产率得到1,1-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)methane
  参考文献：
  名称：

  P 2 O 5 / Al 2 O 3作为无溶剂条件下化学选择性合成1,1-二乙酸酯的高效多相催化剂

  摘要：

  在无溶剂条件下，使用P 2 O 5 / Al 2 O 3和乙酸酐从不同的醛制备酰基的有效且化学选择性的方法。

  DOI：

  10.1016/j.tetlet.2007.02.090

文献信息

• A Mild and Efficient Method for the Chemoselective Synthesis of Acylals from Aldehydes and their Deprotections Catalysed by Ceric Ammonium Nitrate
  作者：Subhas Chandra Roy、Biplab Banerjee

  DOI：10.1055/s-2002-34243

  日期：——

  A mild and efficient method has been developed for the chemoselective synthesis of geminal diacetates (acylals) from aldehydes using acetic anhydride in the presence of a catalytic amount of ceric ammonium nitrate in excellent yield. Ketones are found to be unaffected under the reaction conditions. The deprotections of acylals by using water and ceric ammonium nitrate have also been achieved.

  已经开发了一种温和有效的方法，用于在催化量的硝酸铈铵存在下使用乙酸酐从醛化学选择性合成双乙酸酯（酰基），收率极好。发现酮在反应条件下不受影响。还实现了用水和硝酸铈铵对酰基进行脱保护。
• Amorphous carbon-silica composites bearing sulfonic acid as solid acid catalysts for the chemoselective protection of aldehydes as 1,1-diacetates and for N-, O- and S-acylations
  作者：Princy Gupta、Satya Paul

  DOI：10.1039/c0gc00900h

  日期：——

  Amorphous carbon-silica composites bearing sulfonic acid derived from inexpensive natural organic compounds (glucose, maltose, cellulose, chitosan and starch) were prepared by partial carbonization followed by sulfonation and their catalytic activity was evaluated for the protection of aldehydes as 1,1-diacetates and for N-, O- and S-acylations under solvent-free conditions. Different biomaterials have been chosen, with a view to select the most active solid acid catalyst. Carbon-silica composites were characterized by FTIR, XRD and elemental analysis. Sulfonated carbon-silica composite derived from starch was found to be the most active and could be recycled for several runs without loss of significant activity. It was also characterized by TGA, SEM and TEM.

  通过部分碳化后磺化的方法，制备了由廉价天然有机化合物（葡萄糖、麦芽糖、纤维素、壳聚糖和淀粉）衍生得到的含磺酸基碳-硅复合物，并评估了其在无溶剂条件下保护醛类生成1,1-二乙酸酯以及进行N-、O-和S-酰基化的催化活性。选择了不同的生物质材料，旨在筛选出活性最高的固体酸催化剂。碳-硅复合物通过FTIR、XRD和元素分析进行了表征。由淀粉衍生的磺化碳-硅复合物被发现活性最高，且可回收多次使用而活性无明显损失。该复合物还通过TGA、SEM和TEM进行了表征。
• P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions
  作者：Abdol R. Hajipour、Amin Zarei、Arnold E. Ruoho

  DOI：10.1016/j.tetlet.2007.02.090

  日期：2007.4

  An efficient and chemoselective method for the preparation of acylals from different aldehydes using P2O5/Al2O3 and acetic anhydride under solvent-free conditions.

  在无溶剂条件下，使用P 2 O 5 / Al 2 O 3和乙酸酐从不同的醛制备酰基的有效且化学选择性的方法。
• Synthesis of 1,1-diacetates catalysed by silica-supported boron sulfonic acid under solvent-free conditions and ambient temperature
  作者：Sami Sajjadifar、Sobhan Rezayati

  DOI：10.2478/s11696-013-0480-z

  日期：2014.1.1

  1,1-Diacetates derivatives were prepared using the direct condensation of aldehydes with acetic anhydride in the presence of silica-supported boron sulfonic acid (SiO2/B(SO4H)3) as a tri-functional inorganic Brønsted acid catalyst under solvent-free conditions at ambient temperature. The salient features of this methodology are: (i) cheaper process ready availability of the catalyst; (ii) versatility; (iii) high regio-selectivity of the procedure and recyclable property of the catalyst.

  通过在无溶剂条件下，在室温下使用硅胶负载硼磺酸（SiO2/B(SO4H)3）作为三功能无机布朗斯特酸催化剂，直接将醛类与乙酸酐进行缩合反应，制备了1,1-二醋酸酯衍生物。该方法的显著特点包括：(i) 催化剂价格便宜，易得；(ii) 多功能性；(iii) 过程的高区域选择性和催化剂的可回收性。

• A convenient and efficient protocol for the synthesis of acylals catalyzed by Brønsted acidic ionic liquids under ultrasonic irradiation
  作者：Sanjay P. Borikar、Thomas Daniel

  DOI：10.1016/j.ultsonch.2011.03.022

  日期：2011.9

  The synthesis of acylals (1,1-diacetates) via the reactions of aldehydes with acetic anhydride was carried out in 85-97% yields at room temperature under ultrasound irradiation catalyzed by the Brønsted acidic ionic liquid [bmpy]HSO(4). This method provides several advantages, such as solvent-free conditions, operational simplicity, higher yields, and reduced environmental consequences. The ionic liquid

  在室温下，在布朗斯台德酸性离子液体[bmpy] HSO（4）催化的超声辐射下，通过醛与乙酸酐的反应，合成醛基（1,1-二乙酸酯）的产率为85-97％。该方法具有多种优势，例如无溶剂条件，操作简便，产率更高以及对环境的影响减少。回收离子液体并重新使用。