2-(3',4'-二羟基苯基)乙基甲基碳酸酯 | 953422-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-(3',4'-二羟基苯基)乙基甲基碳酸酯
• 英文名称: 2-(3',4'-dihydrophenyl)ethyl methyl carbonate
• 英文别名: hydroxytyrosol methyl carbonate；3,4-dihydroxyphenylethyl methyl carbonate；2-(3',4'-dihydroxyphenyl)ethyl methyl carbonate；3,4-dihydroxyphenethyl methyl carbonate；hydroxytyrosol carboxymethylated；2-(3,4-Dihydroxy-phenyl)ethyl methyl carbonate；2-(3,4-dihydroxyphenyl)ethyl methyl carbonate
• CAS: 953422-34-9
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: YUVJIRWJKNBBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3',4'-二羟基苯基)乙基甲基碳酸酯 在 氢氧化钾 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到羟基酪醇
  参考文献：
  名称：

  从酪醇或高香草醇方便地合成羟基酪醇及其亲脂性衍生物。

  摘要：

  羟基酪醇是一种天然存在的具有抗氧化性能的邻酚类化合物，它是通过三步高产率程序从天然和低成本的化合物（例如酪醇或高香草醇）合成的。首先，通过使用碳酸二甲酯（DMC）作为试剂/溶剂，对这些化合物的醇基进行有效的化学选择性保护。其次，用2-碘氧基苯甲酸（IBX）或Dess-Martin高碘烷试剂（DMP）氧化并用连二亚硫酸钠（Na 2 S 2 O 4）原位还原，可以制备羧甲基化羟基酪醇。最终，通过温和的水解步骤，以高收率和高纯度获得了羟基酪醇，这已通过NMR光谱和HPLC谱图得到了证实。通过类似的方法，亲脂性羟基酪醇衍生物被用作药物，食品，和化妆品制剂，都准备好了。实际上，首先，通过使用酰氯在没有任何催化剂的情况下对酪醇和高香草醇的醇基团进行化学选择性保护，以获得相应的亲脂性衍生物，然后将这些化合物以高收率和高纯度转化为羟基酪醇衍生物。 IBX或DMP和Na2S2O4的氧化/还原途径。

  DOI：

  10.1021/jf801558z
• 作为产物：
  描述：

  2-(4-hydroxy-3-methoxyphenyl)ethyl methyl carbonate 在 polymer-supported IBX 作用下， 以 dimethyl carbonate 为溶剂， 生成 2-(3',4'-二羟基苯基)乙基甲基碳酸酯
  参考文献：
  名称：

  A novel use of the recyclable polymer-supported IBX: an efficient chemoselective and regioselective oxidation of phenolic compounds. The case of hydroxytyrosol derivatives.

  摘要：

  A useful and novel application of polymer-supported IBX for the chemoselective and regioselective oxidation of phenolic compounds has been described. Hydroxytyrosol and carboxymethylated hydroxytyrosol have been prepared in good conversions and yields under green chemistry conditions in the presence of dimethyl carbonate as the solvent. Polymer supported reagent has been recovered by simple filtration, regenerated and reused for more cycles of oxidation reactions without loss of efficiency. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.037

文献信息

• Lipase-mediated flow synthesis of nature-inspired phenolic carbonates
  作者：Sara Vicinanza、Francesca Annunziata、Desirèe Pecora、Andrea Pinto、Lucia Tamborini

  DOI：10.1039/d3ra04735k

  日期：——

  A facile and convenient lipase-catalyzed flow approach for the chemoselective synthesis of tyrosol and hydroxytyrosol methyl carbonates has been developed. Then, value-added symmetrical tyrosol and hydroxytyrosol carbonates were prepared.

  研究人员开发了一种简便易行的脂肪酶催化流程化学选择性合成酪醇和羟基酪醇甲基碳酸盐的方法。然后，制备出了高附加值的对称酪醇和羟基酪醇碳酸盐。
• 一种超声波促进羟基酪醇碳酸甲酯化的绿色合成方法
  申请人：中国林业科学研究院林产化学工业研究所

  公开号：CN114539061A

  公开（公告）日：2022-05-27

  本发明公开了一种超声波促进羟基酪醇碳酸甲酯化的绿色合成方法，具体步骤：是以羟基酪醇为原料，与适量碳酸二甲酯（DMC）混合后，再添加适量催化剂1,8‑二氮杂双环[5.4.0]十一碳‑7‑烯（DBU），在超声波辅助下强化传质传热，一步法快速合成羟基酪醇的碳酸甲酯，可在30 min内反应转化率超过98%，经硅胶柱色谱纯化后产物纯度达99%以上。本发明专利方法与传统光气法合成相比，反应步数更少，反应时间更短，效率更高，更绿色环保。本发明还具有投入成本低、简单易操作、产品品质优，适合产业化等特点。
• [EN] METHOD FOR PREPARING HYDROXYTYROSOL DERIVATIVES AND OF HYDROXYTYROSOL<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS D'HYDROXYTYROSOL ET D'HYDROXYTYROSOL
  申请人：UNI DEGLI STUDI DELLA TUSCIA

  公开号：WO2008110908A9

  公开（公告）日：2009-02-12
• Chemoselective and efficient carbomethoxylation of the alcoholic chain of phenols by dimethyl carbonate (DMC)
  作者：Roberta Bernini、Enrico Mincione、Fernanda Crisante、Maurizio Barontini、Giancarlo Fabrizi、Patrizia Gentili

  DOI：10.1016/j.tetlet.2007.07.109

  日期：2007.9

  The efficiency of dimethyl carbonate (DMC) as chemoselective carbomethoxylating agent of the alcoholic chain of phenols has been investigated. In the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or sulfuric acid as catalysts, new carbomethoxylated phenolic compounds were obtained in quantitative yields. A new efficient derivatization of the aliphatic alcoholic chain of the precious natural hydroxytyrosol is described, which increases the lipophilicity of the hydroxytyrosol. The antioxidant activity of this new carboxymethylated hydroxytyrosol 8 has been investigated using DPPH radical scavenging test. The results showed that this new compound has an antioxidant activity similar to hydroxytyrosol. (c) 2007 Elsevier Ltd. All rights reserved.
• 2-Arylhydroxytyrosol Derivatives via Suzuki−Miyaura Cross-Coupling
  作者：Roberta Bernini、Sandro Cacchi、Giancarlo Fabrizi、Eleonora Filisti

  DOI：10.1021/ol8012292

  日期：2008.8.21

  2-Arylhydroxytyrosol derivatives, a new class of hydroxytyrosol derivatives, have been prepared in high to excellent yields from the corresponding 2-chloro precursors via Suzuki-Miyaura cross-coupling with arylboronic acids containing electron-donating, electron-withdrawing, as well as ortho substituents. A remarkable halide effect has been observed. 2-lodo- and 2-bromohydroxytyrosol derivatives have been found to be ineffective cross-coupling partners in many cases. The acetonide and carbonate protecting groups can be readily removed.