2-(2'-hydrophenyl)ethyl methyl carbonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2'-hydrophenyl)ethyl methyl carbonate
• 英文别名: 2-(2-(methoxycarbonyloxy)ethyl)phenol；2-(2-Hydroxyphenyl)ethyl methyl carbonate；2-(2-hydroxyphenyl)ethyl methyl carbonate
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: MLAYJMPULUOUKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2'-hydrophenyl)ethyl methyl carbonate 在 2-碘酰基苯甲酸 、 sodium dithionite 作用下， 以 甲醇 、 水 为溶剂， 反应 1.08h， 以64%的产率得到
  参考文献：
  名称：

  Synthesis and Structure/Antioxidant Activity Relationship of Novel Catecholic Antioxidant Structural Analogues to Hydroxytyrosol and Its Lipophilic Esters

  摘要：

  A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.

  DOI：

  10.1021/jf301131a
• 作为产物：
  描述：

  邻羟基苯乙醇 、 碳酸二甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 2.0h， 以98%的产率得到2-(2'-hydrophenyl)ethyl methyl carbonate
  参考文献：
  名称：

  Chemoselective and efficient carbomethoxylation of the alcoholic chain of phenols by dimethyl carbonate (DMC)

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2007.07.109

文献信息

• Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases
  作者：F. Aricò、S. Evaristo、P. Tundo

  DOI：10.1039/c4gc01822b

  日期：——

  A catalytic amount of a nitrogen bicyclic base, i.e., DABCO, DBU or TBD, is effective for the one-pot synthesis of heterocycles from 1,4-, 1,5-diols and 1,4-bifunctional compounds via dimethyl carbonate chemistry under neat conditions. Nitrogen bicyclic bases that were previously shown to have enhanced the reactivity of DMC in methoxycarbonylation reaction by a BAc2 mechanism are herein used for the

  氮双环碱，催化量的即，DABCO，DBU或TBD，有效用于从所述1,4-一锅合成杂环的，1,5-二醇和1,4-双官能化合物通过下碳酸二甲酯化学整洁的条件。先前显示通过B Ac 2机理增强了DMC在甲氧基羰基化反应中的反应性的氮双环碱在本文中首次用作涵盖B Ac 2和B Al 2途径的环化反应的有效催化剂。从D-山梨糖醇和D开始，该合成方法也适用于环糖，异山梨醇和异甘露糖苷的大规模合成。-甘露醇。得到的无水糖醇为纯净的结晶化合物，不需要任何进一步的纯化或结晶。
• Synthesis of Five-Membered Cyclic Ethers by Reaction of 1,4-Diols with Dimethyl Carbonate
  作者：Fabio Aricò、Pietro Tundo、Andrea Maranzana、Glauco Tonachini

  DOI：10.1002/cssc.201100755

  日期：2012.8

  The reaction of 1,4‐diols with dimethyl carbonate in the presence of a base led to selective and high‐yielding syntheses of related five‐membered cyclic ethers. This synthetic pathway has the potential for a wide range of applications. Distinctive cyclic ethers and industrially relevant compounds were synthesized in quantitative yield. The reaction mechanism for the cyclization was investigated. Notably

  1,4-二醇与碳酸二甲酯在碱存在下的反应导致相关五元环醚的选择性和高产合成。这种合成途径具有广泛的应用潜力。以定量产率合成了独特的环状醚和工业上相关的化合物。研究了环化反应的机理。值得注意的是，维持了原料的手性。DFT计算表明，从能量上讲，五元环醚的形成是最有利的途径。通常，可以基于硬-软酸碱理论对这些系统表现出的选择性进行合理化。就计算的能源壁垒而言，这些原则是适用的，
• 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.
• Synthesis and Structure/Antioxidant Activity Relationship of Novel Catecholic Antioxidant Structural Analogues to Hydroxytyrosol and Its Lipophilic Esters
  作者：Roberta Bernini、Fernanda Crisante、Maurizio Barontini、Daniela Tofani、Valentina Balducci、Augusto Gambacorta

  DOI：10.1021/jf301131a

  日期：2012.8.1

  A large panel of novel catecholic antioxidants and their fatty acid or methyl carbonate esters has been synthesized in satisfactory to good yields through a 2-iodoxybenzoic acid (IBX)-mediated aromatic hydroxylation as the key step. The new catechols are structural analogues of naturally occurring hydroxytyrosol (3,4-DHE). To evaluate structure/activity relationships, the antioxidant properties of all catecholic compounds were evaluated in vitro by ABTS assay and on whole cells by DCF fluorometric assay and compared with that of the corresponding already known hydroxytyrosyl derivatives. Results outline that all of the new catechols show antioxidant capacity in vitro higher than that of the corresponding hydroxytyrosyl derivatives. Less evident positive effects have been detected in whole cells experiments. Cytotoxicity experiments, using MTT assay, on a representative set of compounds evidenced no influence in cell survival.