3,3'-diallyl biphenyl-2,4'-diol

• 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: 3,3'-diallyl biphenyl-2,4'-diol
• 英文别名: 3,3'-diallylbiphenyl-2,4'-diol；isohonokiol；2-Allyl-6-(3-allyl-4-hydroxy-phenyl)phenol；2-(4-hydroxy-3-prop-2-enylphenyl)-6-prop-2-enylphenol
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: VJSKNYIUULURAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [1,1-双苯基]-2,4-二醇 在 三氯化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 3,3'-diallyl biphenyl-2,4'-diol
  参考文献：
  名称：

  Synthesis, cytotoxicity, and antiviral activities of new neolignans related to honokiol and magnolol

  摘要：

  A series of new bisphenol derivatives bearing allylic moieties were synthesized as potential analogs of honokiol and/or magnolol. Certain compounds exhibited specific anti-proliferation activity against SVR cells and moderate anti-HIV-1 activity in primary human lymphocytes. Compound 5h was the most potent compound and its anti-tumor activity was evaluated in vivo. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.06.024

文献信息

• SYNTHESIS OF HONOKIOL
  申请人：Colgate-Palmolive Company

  公开号：US20170113989A1

  公开（公告）日：2017-04-27

  Disclosed herein are improved methods for the synthesis of honokiol, as well as methods for the synthesis of 3,3′-di-tert-butyl-5,5′-dimethyl-[1,1′-biphenyl]-2,4′-diol, 3′,5-dimethyl-[1,1′-biphenyl]-2,4′-diol, and 2,4′-dimethoxy-3′,5-dimethyl-1,1′-biphenyl, 3,3′,5,5′-tetra-tert-butyl-[1,1′-biphenyl]-2,4′-diol, and certain tetrasubstituted bisphenols, and uses therefor.

  本文披露了改进的本品合成方法，以及合成3,3′-二叔丁基-5,5′-二甲基-[1,1′-联苯]-2,4′-二酚、3′,5-二甲基-[1,1′-联苯]-2,4′-二酚和2,4′-二甲氧基-3′,5-二甲基-1,1′-联苯、3,3′,5,5′-四叔丁基-[1,1′-联苯]-2,4′-二酚以及某些四取代双酚，及其用途。
• A short and efficient synthesis of honokiol via Claisen rearrangement
  作者：B.V. Subba Reddy、R. Nageshwar Rao、N. Siva Senkar Reddy、R. Somaiah、J.S. Yadav、Ravi Subramanyam

  DOI：10.1016/j.tetlet.2013.12.079

  日期：2014.1

  concise and efficient total synthesis of honokiol, a biphenyl-type neolignan is accomplished in six steps using readily available and cost-effective reagents. The synthetic route involves mainly the Grignard reaction, iodine mediated aromatization, and Claisen rearrangement as key steps. A predominant formation of honokiol (1a) was observed in the Claisen rearrangement under microwave irradiation whereas

  使用现成的和具有成本效益的试剂，可以通过六个步骤完成厚朴酚（联苯型新木酚素）的简明高效的全合成。合成途径主要涉及格氏反应，碘介导的芳构化和克莱森重排等关键步骤。在微波辐射下的克莱森重排中观察到主要的厚朴酚（1a）的形成，而在常规条件下异厚朴酚（1b）是主要产物。
• [EN] IMPROVED SYNTHESIS OF HONOKIOL<br/>[FR] SYNTHÈSE AMÉLIORÉE D'HONOKIOL
  申请人：COLGATE PALMOLIVE CO

  公开号：WO2017070568A1

  公开（公告）日：2017-04-27

  Disclosed herein are improved methods for the synthesis of honokiol, as well as methods for the synthesis of 3,3'-di-tert-butyl-5,5'-dimethyl-[1,1'-biphenyl]-2,4'-diol, 3',5-dimethyl-[1,1'-biphenyl]-2,4'-diol, and 2,4'-dimethoxy-3',5-dimethyl-1,1'-biphenyl, 3,3',5,5'-tetra-tert-butyl-[1,1'-biphenyl]-2,4'-diol, and certain tetrasubstituted bisphenols, and uses therefor.

  本文揭示了改进的紫草酚合成方法，以及合成3,3'-二叔丁基-5,5'-二甲基-[1,1'-联苯]-2,4'-二酚、3',5-二甲基-[1,1'-联苯]-2,4'-二酚和2,4'-二甲氧基-3',5-二甲基-1,1'-联苯、3,3',5,5'-四叔丁基-[1,1'-联苯]-2,4'-二酚和某些四取代双酚的方法及其用途。
• Synthesis of honokiol analogues and evaluation of their modulating action on VEGF protein secretion and telomerase-related gene expressions
  作者：María Sánchez-Peris、Juan Murga、Eva Falomir、Miguel Carda、Juan Alberto Marco

  DOI：10.1111/cbdd.12880

  日期：2017.4

  A group of 36 biphenyl derivatives structurally related to honokiol were synthesized by means of Suzuki coupling reactions. Their cytotoxicities were evaluated and compared to that of honokiol. Some of the compounds were then evaluated for their ability to downregulate the secretion of the VEGF protein and the expression of the VEGF, hTERT, and c‐Myc genes; the two latter involved in the activation of telomerase in tumoral cells. Some of the synthetized derivatives showed promising pharmacological features as they exhibited IC50 values in low micromolar range, good therapeutic margins, and a multiple mode of action on tumor cells based on the inhibition of VEGF and, at the same time, of the expression of genes related to the activation of telomerase.
• Biphenyl derivative, nerve cell degeneration repairing or protecting agent and process for preparing a phenyl derivative contained in the agent
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0382213B1

  公开（公告）日：1995-05-10