(E)-1-<3,4-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene | 150258-78-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-<3,4-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene
• 英文别名: trans-3,3',4,5'-tetrabenzyloxystilbene；3,3',4',5-tetrabenzyloxy stilbene；(E)-1-(3,4-dibenzyloxyphenyl)-2-(3,5-dibenzyloxyphenyl)ethylene；1,2-bis(benzyloxy)-4-{(E)-2-[3,5-bis(benzyloxy)phenyl]vinyl}benzene；1-[(E)-2-[3,4-bis(phenylmethoxy)phenyl]ethenyl]-3,5-bis(phenylmethoxy)benzene
• CAS: 150258-78-9
• 化学式: C₄₂H₃₆O₄
• 分子量: 604.745
• InChiKey: RVNQYBQRAQHTGF-QURGRASLSA-N

物化性质

• 沸点：
  764.6±55.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-<3,4-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 在 三溴化硼 、 维生素 C 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以32%的产率得到白皮杉醇
  参考文献：
  名称：

  피스아타놀 유도체 합성방법 및 피스아타놀 유도체를 포함하는 항염증 약학 조성물

  摘要：

  使用VTG-HNR反应，Colvin重排和Sonogashira反应合成了易于合成Piceatannol诱导体。结果表明，合成的化合物在LPS诱导的RAW264.7巨噬细胞中显示出显著的抗炎活性，化合物6~8在10μM浓度下表现出显著活性，其中化合物7（90.1%）、化合物8（60.8%）、化合物6（55.2%）不表现细胞毒性。

  公开号：

  KR20170097422A
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 三溴化磷 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 33.5h， 生成 (E)-1-<3,4-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene
  参考文献：
  名称：

  Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogs of piceatannol

  摘要：

  A series of hydroxylated trans-stilbenes related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxystilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function. A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product. Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly. The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.

  DOI：

  10.1021/jm00072a015

文献信息

• 一种合成羟基芪类化合物的新方法
  申请人：中国科学院成都有机化学有限公司

  公开号：CN106336347B

  公开（公告）日：2020-08-18

  本发明公开了一种合成羟基芪类化合物新方法。所要求保护的方法为：在有机溶剂中，一定温度下，通过钯碳/甲酸铵体系催化脱除苄基保护基，得到羟基芪类化合物。该方法具有反应条件温和，操作简单，试剂毒性小，安全，收率高，适用范围广，成本低，适合较大量生产等优点。
• 一种人工合成全反式白藜芦醇及其衍生物的方法
  申请人：杭州瑞树生化有限公司

  公开号：CN106995364A

  公开（公告）日：2017-08-01

  本发明公开一种人工合成全反式白藜芦醇及其衍生物的方法。方法通过构筑共轭稠环的方式，制备了全反式白藜芦醇及其衍生物的前驱体，由此完全限定了白藜芦醇及其衍生物的全反式空间结构，制备出全反式白藜芦醇及其衍生物。本发明中的制备1,2‑二苯乙烯或其衍生物方法，所得产品为全反式构型，符合生物活性物质化学品的需要。相比于以往工艺，本发明具有工艺简单，条件温和，符合绿色化学概念。
• Dimerization of piceatannol by Momordica charantia peroxidase and α-glucosidase inhibitory activity of the biotransformation products
  作者：Xiang Wan、Xiao-Bing Wang、Ming-Hua Yang、Jun-Song Wang、Ling-Yi Kong

  DOI：10.1016/j.bmc.2011.07.032

  日期：2011.9

  Stilbenes, especially those oligomers, have great potential to be antihyperglycemic agents. In this study, eight stilbene dimers, including five new ones, were obtained by biotransformation of piceatannol using Momordica charantia peroxidase (MCP) for the first time. Their structures were established on the basis of spectroscopic evidences. These piceatannol dimers displayed potential a-glucosidase inhibitory activities, and trans double bond, tetrahydrofuran ring, and free adjacent phenolic dihydroxyls were found to be important for their activities. Enzymatic biotransformation of stilbenes by M. charantia peroxidase (MCP) was showed to be a prominent way to produce oligomeric stilbenes for antihyperglycemic development. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogs of piceatannol
  作者：Kshitij Thakkar、Robert L. Geahlen、Mark Cushman

  DOI：10.1021/jm00072a015

  日期：1993.10

  A series of hydroxylated trans-stilbenes related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxystilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function. A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product. Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly. The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.
• 피스아타놀 유도체 합성방법 및 피스아타놀 유도체를 포함하는 항염증 약학 조성물
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR20170097422A

  公开（公告）日：2017-08-28

  비티그-호너 반응, 콜빈 재배열 및 소노가시라 반응을 이용하여 피스아타놀 유도체를 용이하게 합성하였다. LPS로 유도된 RAW264.7 대식세포에서 합성된 화합물들에 대하여 항염증 활성을 조사한 결과, 화합물 6~8이 10 μM 농도에서 현저한 활성을 나타내었고, 화합물 7 (90.1%), 화합물 8 (60.8%), 화합물 6 (55.2%)은 세포독성을 나타내지 않았다.

  使用VTG-HNR反应，Colvin重排和Sonogashira反应合成了易于合成Piceatannol诱导体。结果表明，合成的化合物在LPS诱导的RAW264.7巨噬细胞中显示出显著的抗炎活性，化合物6~8在10μM浓度下表现出显著活性，其中化合物7（90.1%）、化合物8（60.8%）、化合物6（55.2%）不表现细胞毒性。