4-(hydroxyethyl)-1,2-diacetoxybenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(hydroxyethyl)-1,2-diacetoxybenzene
• 英文别名: 3,4-Diacetoxyphenethyl alcohol；[2-acetyloxy-4-(2-hydroxyethyl)phenyl] acetate
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: BFNGYTNRQSRSFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 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：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(hydroxyethyl)-1,2-diacetoxybenzene 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 4-[2-(2-chlorophenoxy)ethyl]benzene-1,2-diol
  参考文献：
  名称：

  羟基酪醇与其他天然酚类片段的结合：从废物到抗氧化剂和抗肿瘤化合物

  摘要：

  羟基酪醇是一种可以从橄榄厂废水中提取的天然多酚，通过与其他天然衍生的（多）酚类片段结合，转化为一系列更复杂和亲脂的类似物。使用醚和三唑接头。准备了一个小型化合物库，强调步骤经济和操作简单。在自由基清除试验以及对肿瘤细胞的细胞毒性试验中，这些物质中的一些被证明具有与母体羟基酪醇相同或优于母体羟基酪醇的活性。

  DOI：

  10.1002/ejoc.201500931
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 4-(hydroxyethyl)-1,2-diacetoxybenzene
  参考文献：
  名称：

  A Highly Convenient Synthesis of Hydroxytyrosol and Its Recovery from Agricultural Waste Waters

  摘要：

  Hydroxytyrosol, a polyphenol with very interesting antioxidant properties, which naturally occurs in virgin olive oil and mainly in olive oil mill waste waters, was synthesized by reducing 3,4-dihydroxyphenylacetic acid with LiAIH(4) in tetrahydrofuran under refluxing for 2 h. The yield of reaction was 82.8%. The spectroscopic and HPLC data of the synthesized compound proved to coincide fully with those of a pure sample obtained by the chromatographic recovery from olive oil mill waste waters (yield = 91 mg/L). This synthetic method appears to be the most convenient compared with those reported in the literature and is more convenient than the chromatographic recovery. The tri- and diacetyl derivatives of the synthetic compound were also prepared for structure-bioactivity relationship studies. A brief discussion is given on the economical and ecological aspects regarding the production of hydroxytyrosol.

  DOI：

  10.1021/jf9809030

文献信息

• One-Pot Relay Glycosylation
  作者：Xiong Xiao、Jing Zeng、Jing Fang、Jiuchang Sun、Ting Li、Zejin Song、Lei Cai、Qian Wan

  DOI：10.1021/jacs.0c00447

  日期：2020.3.25

  A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one-pot. A wide range of substrates are well-accommodated to furnish

  已经建立了一种新型的一锅接力糖基化。该协议的特点是仅用一当量的三氟甲磺酸酐构建两个糖苷键。该方法利用原位生成的环硫锍离子作为中继激活剂，直接在一锅法中激活新形成的硫糖苷。广泛的底物适用于提供线性和支化寡糖。该方法的合成效用和优势已通过快速获得天然存在的苯乙酮糖苷 kankanoside F 和树脂糖苷 merremoside D 得到证明。
• [EN] PROCESS FOR THE PRODUCTION OF OLEOCANTHAL, OLEACEIN AND THEIR ANALOGUES<br/>[FR] PROCÉDÉ DE PRODUCTION D'OLÉOCANTHAL, D'OLÉACEINE ET DE LEURS ANALOGUES
  申请人：NATIONAL AND KAPODISTRIAN UNIV OF ATHENS

  公开号：WO2021121925A1

  公开（公告）日：2021-06-24

  A process for the production of a compound according to Formula (I), such as oleocanthal or oleacein, starting from oleuropein. The process provides the dialdehyde core of oleocanthal, oleacein and their analogues having the required stereochemistry. Furthermore, the process can be used for the production of a large number of structurally diverse products by varying the structure of the alcohol moiety in the esterification step.

  根据公式(I)，从欧洲橄榄叶苷开始生产化合物的方法，例如欧力坎醇或欧力酮。该方法提供了欧力坎醇、欧力酮及其类似物所需立体化学结构的二醛核心。此外，通过在酯化步骤中改变醇基的结构，该方法可用于生产大量结构多样的产物。
• Synthesis of Tyrosol and Hydroxytyrosol Glycofuranosides and Their Biochemical and Biological Activities in Cell-Free and Cellular Assays
  作者：Peter Kis、Eva Horváthová、Eliška Gálová、Andrea Ševčovičová、Veronika Antalová、Elena Karnišová Potocká、Vladimír Mastihuba、Mária Mastihubová

  DOI：10.3390/molecules26247607

  日期：——

  Tyrosol (T) and hydroxytyrosol (HOT) and their glycosides are promising candidates for applications in functional food products or in complementary therapy. A series of phenylethanoid glycofuranosides (PEGFs) were synthesized to compare some of their biochemical and biological activities with T and HOT. The optimization of glycosylation promoted by environmentally benign basic zinc carbonate was performed

  酪醇 (T) 和羟基酪醇 (HOT) 及其糖苷是用于功能性食品或补充疗法的有希望的候选者。合成了一系列苯乙醇呋喃糖苷 (PEGFs) 以比较其与 T 和 HOT 的一些生化和生物活性。对环境无害的碱式碳酸锌促进的糖基化进行优化，以制备 HOT α-L-阿拉伯糖苷、β-D-apio- 和 β-D-呋喃核糖苷。通过酶促转果糖基化 T 和 HOT 制备的 T 和 HOT β-D-呋喃果糖苷也包括在比较研究中。使用无细胞测定法测定了 T、HOT 和 PEGFs 对质粒 DNA 的抗氧化能力和 DNA 保护潜力。使用彗星试验评估了所研究化合物对人肝癌 HepG2 细胞的 DNA 损伤潜力及其对 HepG2 细胞对过氧化氢的 DNA 保护潜力。实验揭示了所研究化合物的一系列不同活性。HOT 和 HOT β-D-fructofuranoside 似乎是质粒 DNA 和 HepG2 细胞的最佳清除剂和保护剂。T
• Direct and mediated effects onBactrocera oleae (Gmelin) (Diptera; Tephritidae) of natural polyphenols and some of related synthetic compounds: Structure-activity relationships
  作者：Renato Capasso、Antonio Evidente、Ermenegildo Tremblay、Andrea Sala、Carmine Santoro、Gennaro Cristinzio、Francesco Scognamiglio

  DOI：10.1007/bf02059753

  日期：1994.5

  Among the main polyphenols occurring in olive oil vegetation waters (VW), catechol showed the most deterrent action on the oviposition of Bactrocera oleae (Gmelin); 4-methylcatechol was less active, whereas hydroxytyrosol and tyrosol were inactive. In contrast, synthetic o-quinone was found to be stimulant at 7.5 x 10(-2) M. Two other synthetic derivatives of catechol, diacetylcatechol and guaiacol, were also deterrent, suggesting these compounds undergo a biochemical transformation into catechol by means of the bacterial symbionts of B. oleae. VW and their phenolic extracts showed deterrence only when highly concentrated, while natural olive juice was strongly deterrent. Experiments carried out to evaluate the effect of olive juice and catechol on the fecundity of B. oleae showed that they strongly reduce this function. Moreover, the possible utilization of VW and their bioactive polyphenols in protection of olives against Batrocera oleae is discussed.
• Synthetic phenylethanoid glycoside derivatives as potent neuroprotective agents
  作者：Ying-Guo Liu、Xiaxi Li、De-Cai Xiong、Binhan Yu、Xiaoping Pu、Xin-Shan Ye

  DOI：10.1016/j.ejmech.2015.03.038

  日期：2015.5

  Several phenylethanoid glycoside derivatives were designed and synthesized. Most of the synthetic compounds showed significant neuroprotective effects, including antioxidative and anti-apoptotic properties. Specifically, target compounds displayed potent effects against various toxicities such as H2O2 and 6-hydroxydopamine (6-OHDA) in PCl2 cells. Among the synthetic derivatives, three compounds (5, 6, 8) exhibited much superior activities to the marketed drug Edaravone. The compounds were able to prevent the 6-OHDA-induced damage in PCl2 cells in a dose-dependent manner. The antiapoptotic effects could be observed via cell morphological changes. Moreover, the compounds significantly reduced the intracellular ROS increase resulting from 6-OHDA treatment. The preliminary structure activity relationships were also explored. Compounds 5, 6, 8 may hold the potential as promising neuroprotective agents and new lead compounds for the treatment of neurodegenerative diseases or cerebral ischemia. (C) 2015 Elsevier Masson SAS. All rights reserved.