5,5'-diallyl-(1,1'-biphenyl)-2,2',3,3'-tetraol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-diallyl-(1,1'-biphenyl)-2,2',3,3'-tetraol
• 英文别名: 5,5'-diallylbiphenyl-2,3,2',3'-tetraol；3,3'-dihydroxymagnolol；3-(2,3-Dihydroxy-5-prop-2-enylphenyl)-5-prop-2-enylbenzene-1,2-diol
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: ZOHIBQDPTKRFSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  去氢双丁香酚 在 吡啶 、 aluminium(III) iodide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以96%的产率得到5,5'-diallyl-(1,1'-biphenyl)-2,2',3,3'-tetraol
  参考文献：
  名称：

  吡啶改善了三碘化铝诱导的烷基邻羟基苯基醚的选择性裂解：一种通过丁香酚去甲基化制备羟基茶维醇的实用且有效的方法

  摘要：

  丁香酚与三碘化铝的去甲基化由于意外的氢化副反应而变得复杂。氢化通过级联去质子化、氢碘化和氢卤交换过程进行，并且可以通过提前抑制氢碘化来防止。因此开发了一种实用的去甲基化程序，通过使用吡啶作为添加剂以基本定量的产率提供羟基茶维醇。该方法对裂解烷基邻羟基苯基醚具有选择性，并且与多种官能团相容。

  DOI：

  10.1055/s-0035-1588889

文献信息

• Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers
  作者：Dayong Sang、Jiahui Wang、Yun Zheng、Jianyuan He、Caili Yuan、Qing An、Juan Tian

  DOI：10.1055/s-0036-1588755

  日期：2017.6

  is applicable to variant alkyl aryl ethers such as eugenol, vanillin, ortho-vanillin and methyl eugenol. Suitable substrates are not limited to alkyl o-hydroxyphenyl ethers. A practical procedure for the cleavage of alkyl aryl ethers containing labile functional groups has been developed using aluminum triiodide as the ether cleaving reagent. Carbodiimides, typically used as dehydration reagents for

  摘要 使用三碘化铝作为醚裂解剂，已经开发了裂解含有不稳定官能团的烷基芳基醚的实用方法。发现碳二亚胺通常用作脱水剂，用于胺和羧酸的偶联以产生酰胺键，是防止碘酸不稳定基团变质的有效碘化氢清除剂。该方法适用于变体烷基芳基醚，例如丁子香酚，香兰素，邻香兰素和甲基丁香酚。合适的底物不限于烷基邻羟基苯醚。 使用三碘化铝作为醚裂解剂，已经开发了裂解含有不稳定官能团的烷基芳基醚的实用方法。发现碳二亚胺通常用作脱水剂，用于胺和羧酸的偶联以产生酰胺键，是防止碘酸不稳定基团变质的有效碘化氢清除剂。该方法适用于变体烷基芳基醚，例如丁子香酚，香兰素，邻香兰素和甲基丁香酚。合适的底物不限于烷基邻羟基苯醚。
• 一种苯基烷基醚的醚键断裂方法
  申请人：荆楚理工学院

  公开号：CN106866377B

  公开（公告）日：2020-06-09

  本发明公开了一种苯基烷基醚的醚键断裂方法，该方法是：在有机溶剂中，在三碘化铝和碳二亚胺存在的条件下，苯基烷基醚在‑20℃至回流的温度下发生醚键断裂反应，生成苯酚及其衍生物。该方法条件温和，操作简便，而且产率高，适用的苯基烷基醚范围广。
• Design and synthesis of novel magnolol derivatives as potential antimicrobial and antiproliferative compounds
  作者：Srinivas Jada、Mahendhar Reddy Doma、Parvinder Pal Singh、Suresh Kumar、Fayaz Malik、Akash Sharma、Inshad Ali Khan、G.N. Qazi、H.M. Sampath Kumar

  DOI：10.1016/j.ejmech.2011.12.039

  日期：2012.5

  A series of novel magnolol derivatives were synthesised and evaluated for in vitro antimicrobial and antiproliferative activities. We found that most of the compounds were effective inhibitors of Staphylococcus aureus, MRSA and VRE with MIC in the range of 1-64 mu g/mL and MBC in the range of 1-128 mu g/mL. Few derivatives also exhibited promising antifungal activity. Some magnolol analogues exhibited promising antiproliferative activity than parent magnolol when tested against three human cancer cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Chemoenzymatic Synthesis and α-Glucosidase Inhibitory Activity of Dimeric Neolignans Inspired by Magnolol
  作者：Luana Pulvirenti、Vera Muccilli、Nunzio Cardullo、Carmela Spatafora、Corrado Tringali

  DOI：10.1021/acs.jnatprod.7b00250

  日期：2017.5.26

  A chemoenzymatic synthesis of a small library of dimeric neolignans inspired by magnolol (1) is reported. The 2-iodoxybenzoic acid (IBX)-mediated regioselective orthohydroxylation of magnolol is described, affording the bisphenols 6 and 7. Further magnolol analogues (12, 13, 15-17, 19-23) were obtained from eugenol (3), tyrosol (4), and homovanillic alcohol (5), through horseradish peroxidase (HRP)-mediated oxidative coupling and regioselective orthohydroxylation or ortho-demethylation in the presence of MX, followed by reductive treatment with Na2S2O4. A chemoselective protection/deprotection of the alcoholic group of 4 and 5 was carried out by lipase-mediated acetylation/deacetylation. The dimeric neolignans, together with 1 and honokiol (2), were evaluated as inhibitors of yeast a-glucosidase, in view of their possible utilization and optimization as antidiabetic drugs. The synthetic analogues of magnolol showed a strong inhibitory activity with IC50 values in the range 0.15-4.1 mu M, much lower than those of honokiol and the reference compounds quercetin and acarbose. In particular, a very potent inhibitory activity, with an IC50 of 0.15 mu M, was observed for 1,1'-dityrosol-8,8'-diacetate (15), and comparable inhibitory activities were also shown by bisphenols 6 (0.49 mu M), 13 (0.50 mu M), and 22 (0.86 mu M). A kinetic study showed that 15 acts as a competitive inhibitor, with a K-i value of 0.86 mu M.
• Cytotoxic neolignans: an SAR study
  作者：Zwe-Ling Kong、Shin-Cheng Tzeng、Yeuk-Chuen Liu

  DOI：10.1016/j.bmcl.2004.10.011

  日期：2005.1

  The neolignans, magnolol 1 and honokiol 2 have been reported to inhibit the growth of several tumor cell lines in vitro and in vivo. The chemical structure of magnolol and honokiol consists of biphenyl skeleton with phenolic and allylic functionalities. Analogs of 1 and 2 containing different substitution have been studies for their effect on the growth of Hep-G2 and their structure-activity relationships were reported in this work. (C) 2004 Elsevier Ltd. All rights reserved.