(E)-1-<3,5-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene | 150258-79-0

• 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-<3,5-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene
• 英文别名: (E)-1-(3,5-bis(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl)ethene；1-[(E)-2-[3,5-bis(phenylmethoxy)phenyl]ethenyl]-3,5-bis(phenylmethoxy)benzene
• CAS: 150258-79-0
• 化学式: C₄₂H₃₆O₄
• 分子量: 604.745
• InChiKey: GSVKPGXXGXGEDC-QURGRASLSA-N

物化性质

• 沸点：
  769.6±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-<3,5-bis(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到(E)-3,3',5,5'-tetrahydroxystilbene
  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
• 作为产物：
  描述：

  3,5-二苄氧基苯甲醇 在 三溴化磷 、 四丁基碘化铵 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 (E)-1-<3,5-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

• Photoisomerization of Stilbene Dendrimers: The Need for a Volume-conserving Isomerization Mechanism¶
  作者：Mayuko Uda、Takuo Mizutani、Junpei Hayakawa、Atsuya Momotake、Masashi Ikegami、Ritsuko Nagahata、Tatsuo Arai

  DOI：10.1562/0031-8655(2002)076<0596:posdtn>2.0.co;2

  日期：——

  Abstract Highly branched stilbene dendrimers were synthesized and their photochemical behavior was studied. Even the stilbene dendrimer with molecular weight over 6500 underwent trans–cis isomerization in the excited singlet state within the lifetime of 10 ns. The photoisomerization of C=C double bond of stilbene dendrimers in the excited state may proceed by a volume-conserving novel mechanism such

  摘要 合成了高度支化的二苯乙烯树枝状大分子并研究了它们的光化学行为。即使是分子量超过 6500 的二苯乙烯树枝状聚合物在 10 ns 的寿命内在激发单线态下也经历了反式-顺式异构化。激发态二苯乙烯树枝状聚合物的 C=C 双键的光异构化可以通过体积守恒的新机制进行，例如 hula-twist，而不是基于荧光和异构化实验的围绕 C=C 双键的常规 180°旋转。