5-烯丙基-[1,1'-联苯基]-2,4'-二醇 | 1253950-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-烯丙基-[1,1'-联苯基]-2,4'-二醇
• 英文名称: 5-allyl-[1,1'-biphenyl]-2,4'-diol
• 英文别名: 5-allylbiphenyl-2,4'-diol；2-(4-Hydroxyphenyl)-4-prop-2-enylphenol
• CAS: 1253950-18-3
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: PHARZSAWYNACPU-UHFFFAOYSA-N

物化性质

• 熔点：
  104-106 °C
• 沸点：
  375.4±32.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-烯丙基苯甲醚 在 2-双环己基膦-2',6'-二甲氧基联苯 、 咪唑 、 盐酸 、 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四甲基乙二胺 、 三氯化硼-甲硫醚 、 potassium tert-butylate 、 水 、 溴 、 仲丁基锂 、 sodium sulfate 、 cesium fluoride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 5-烯丙基-[1,1'-联苯基]-2,4'-二醇
  参考文献：
  名称：

  合成法呢酮/法呢素家族天然产物的策略：三环核的合成†

  摘要：

  提出了天然产物法呢素/法呢酮家族的核心环结构的合成。通用策略基于生物合成推测，并利用级联反应，该级联反应通过去质子化-氧基-迈克尔-维蒂希（Michael-Wittig）烯化序列将螺环二烯酮转化为核心环系统。这项研究代表了该天然产物家族的首次合成工作。

  DOI：

  10.1039/c2ob25489a

文献信息

• Structural Modification of Honokiol, a Biphenyl Occurring in Magnolia officinalis: the Evaluation of Honokiol Analogues as Inhibitors of Angiogenesis and for Their Cytotoxicity and Structure–Activity Relationship
  作者：Liang Ma、Jinying Chen、Xuewei Wang、Xiaolin Liang、Youfu Luo、Wei Zhu、Tianen Wang、Ming Peng、Shucai Li、Shi Jie、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1021/jm200830u

  日期：2011.10.13

  Honokiol, widely known as an antitumor agent, has been used as an antiangiogenesis drug lead. In this paper, 47 honokiol analogues and derivatives were investigated for their antiangiogenic activity by application of the transgenic zebrafish screening model, antiproliferative and cytotoxic activity against HUVECs, and three tumor cell lines by MTT assay. 3',5-Diallyl-2, 4'-dihydroxy-[1,1'-biphen-yl]-3,5'-dicarbaldehyde (8c) was found to suppress the newly grown segmental vessels from the dorsal aorta of zebrafish and prevent inappropriate vascularization as well as exhibit more potent inhibitory effects on the proliferation of HUVECs, A549, HepG2, and LL/2 cells (IC50 = 15.1, 30.2, 10.7, and 21.7 mu M, respectively) than honokiol (IC50 = 52.6, 35.0, 16.5, and 65.4 mu M, respectively). Analogue 8c also effectively inhibited the migration and capillary-like tube formation of HUVECs in vitro. The antiangiogenic effect and antiproliferative activity of these structurally modified honokiol analogues and derivatives have led to the establishment of a structure-activity relationship.
• A concise synthesis of honokiol
  作者：Ross M. Denton、James T. Scragg、Adrià M. Galofré、Xiechao Gui、William Lewis

  DOI：10.1016/j.tet.2010.08.005

  日期：2010.10

  Two approaches to the synthesis of the plant-derived biaryl neolignan honokiol are described. The second approach provided the natural product in either four steps with 34% overall yield or five steps and 55% overall yield. (C) 2010 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF DIHYDROHONOKIOL COMPOSITIONS
  申请人：Board of Regents,The University of Texas System

  公开号：EP0991614A1

  公开（公告）日：2000-04-12
• [EN] SYNTHESIS OF DIHYDROHONOKIOL COMPOSITIONS<br/>[FR] SYNTHESE DE COMPOSITIONS DE DIHYDROHONOKIOL
  申请人：UNIV TEXAS

  公开号：WO1999000346A1

  公开（公告）日：1999-01-07

  The synthesis and use of the anxiolytic compound dihydrohonokiol, its derivatives, analogs and homologs are disclosed. A method for reducing anxiety in a mammal is also disclosed.
• [EN] SYNTHESIS OF DIHYDROHONOKIOL COMPOSITIONS<br/>[FR] SYNTHESE DE COMPOSITIONS A BASE DE DIHYDROHONOKIOL
  申请人：UNIV TEXAS

  公开号：WO2000040532A2

  公开（公告）日：2000-07-13

  The synthesis and use of the anxiolytic compound dihydrohonokiol, its derivatives, analogs and homologs are disclosed. A method for reducing anxiety in a mammal is also disclosed.