3-Acetoxy-4-methoxy-1-(diacetoxymethyl)benzene | 71155-68-5

• 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-4-methoxy-1-(diacetoxymethyl)benzene
• 英文别名: 2-acetoxy-4-diacetoxymethyl-1-methoxy-benzene；2-Acetoxy-4-diacetoxymethyl-1-methoxy-benzol；Isovanillin-triacetat；[3-(Acetyloxy)-4-methoxyphenyl]methanediyl diacetate；[5-(diacetyloxymethyl)-2-methoxyphenyl] acetate
• CAS: 71155-68-5
• 化学式: C₁₄H₁₆O₇
• 分子量: 296.277
• InChiKey: NKTWGBVMIBQCSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Acetoxy-4-methoxy-1-(diacetoxymethyl)benzene 在 iron(III) sulfate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以90%的产率得到5-甲酰基-2-甲氧基苯基 乙酸酯
  参考文献：
  名称：

  Li, Lingjun; Zhang, Xinying; Zhang, Guisheng, Journal of Chemical Research, 2004, # 1, p. 39 - 40

  摘要：

  DOI：
• 作为产物：
  描述：

  异香兰素 、 乙酸酐 以 neat (no solvent) 为溶剂， 反应 0.07h， 以98%的产率得到3-Acetoxy-4-methoxy-1-(diacetoxymethyl)benzene
  参考文献：
  名称：

  SiO2 @ FeSO4纳米复合材料在无溶剂条件下绿色合成醛类绿色合成1,1-二酸酯

  摘要：

  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。

  DOI：

  10.4067/s0717-97072016000100007

文献信息

• An Efficient Method for the Synthesis of Acylals from Aldehydes under Solvent‐Free Conditions Catalyzed by Antimony Trichloride
  作者：Asish K. Bhattacharya、Mohammad Mujahid、Arvind A. Natu

  DOI：10.1080/00397910701651284

  日期：2007.12.1

  Abstract A mild and efficient method has been developed for the preparation of acylals from aldehydes catalyzed by antimony trichloride under solvent‐free conditions in very good to excellent yields. The easy availability, low cost, and ease of handling of the catalyst make this procedure especially attractive for large‐scale synthesis.

  摘要 开发了一种温和有效的方法，用于在无溶剂条件下以非常好的收率由三氯化锑催化的醛制备酰基醛。该催化剂易于获得、成本低且易于处理，这使得该方法对大规模合成特别有吸引力。
• Cobalt(II)-catalyzed reaction of aldehydes with acetic anhydride under an oxygen atmosphere: scope and mechanism
  作者：Beena Bhatia、T. Punniyamurthy、Javed Iqbal

  DOI：10.1021/jo00072a041

  日期：1993.9

  The reaction of aldehydes with acetic anhydride in the presence of catalytic cobalt(II) chloride under an oxygen atmosphere at ambient temperature is dependent upon the reaction medium. Aliphatic aldehydes react in acetonitrile to give 1,2-diones whereas the aromatic aldehydes are acylated to yield the corresponding acylals. On the other hand, carboxylic acids are obtained from aliphatic and aromatic aldehydes by conducting the reaction in dichloroethane or benzene. Cobalt(II) chloride in acetonitrile catalyzes the conversion of aliphatic aldehydes to the corresponding anhydrides in the absence of acetic anhydride whereas aromatic aldehydes remain largely unaffected under these conditions. A preliminary mechanistic study in three different solvents (i.e. acetonitrile, dichloroethane, and DMF) has revealed that in acetonitrile and in the presence of acetic anhydride, aliphatic aldehydes behave differently than aromatic aldehydes. Some trapping experiments using methyl acrylate and stilbene have been conducted to demonstrate the occurrence of an acyl cobalt and peroxyacyl cobalt intermediate during these reactions.
• Zur Synthese der Homoisovanillinsäure
  作者：H. W. Bersch

  DOI：10.1002/ardp.19392770606

  日期：——
• ACTION OF BROMINE ON VANILLIN, ISOVANILLIN, AND SOME OF THEIR DERIVATIVES, AND MODIFICATION OF THE DIRECTIVE INFLUENCE OF HYDROXYL IN THESE COMPOUNDS
  作者：L. CHAS. RAIFORD、MELVILLE F. RAVELY

  DOI：10.1021/jo01208a017

  日期：1940.3
• Niu, Hongying; Zhang, Xinying; Guo, Haiming, Journal of Chemical Research, 2004, # 11, p. 764 - 765
  作者：Niu, Hongying、Zhang, Xinying、Guo, Haiming、Wang, Jianji

  DOI：——

  日期：——