(E)-1-(3-hydroxyphenyl)-2-(3-hydroxyphenyl)ethene | 70709-65-8

• 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-hydroxyphenyl)-2-(3-hydroxyphenyl)ethene
• 英文别名: (E)-1,2-bis(3-hydroxyphenyl)ethene；E-3,3'-[1,2-ethenediyl]bisphenol；(E)-3-(3-hydroxystyryl)phenol；3,3'-dihydroxy-trans-stilbene；trans-3,3'-dihydroxystilbene；(E)-3,3'-dihydroxystilbene；3-[2-(3-hydroxyphenyl)-(E)-1-ethenyl]phenol；3-[(E)-2-(3-hydroxyphenyl)ethenyl]phenol
• CAS: 70709-65-8；135781-00-9；143207-60-7
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: VLOHFQFIKQIMBT-BQYQJAHWSA-N

物化性质

• 沸点：
  427.9±34.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(3-hydroxyphenyl)-2-(3-hydroxyphenyl)ethene 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、700.01 kPa 条件下， 反应 5.0h， 以99%的产率得到3,3'-(ethane-1,2-diyl)diphenol
  参考文献：
  名称：

  通过可再生原料的异构复分解合成潜在的双酚A替代品

  摘要：

  引入异构化复分解作为一种可持续的方法，可以从丁香油成分丁香酚和腰果壳液中提取腰果酚来生产二羟基hydroxy衍生物。二羟基苯乙烯的氢化提供了它们的二（羟基苯基）乙烷类似物。在将这些单体转化为聚碳酸酯和硫醇烯聚合物的初步研究中，他们支持了其替代源自汽油的双酚A（BPA）的潜力。发现腰果酚衍生的单体的雌激素活性与已知的内分泌干扰物BPA在同一范围内。相反，发现丁香酚来源的材料是非雌激素的，这为生物基食品包装材料开辟了新的前景。

  DOI：

  10.1039/c7gc00553a
• 作为产物：
  描述：

  间羟基苯甲醛 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.33h， 以84%的产率得到(E)-1-(3-hydroxyphenyl)-2-(3-hydroxyphenyl)ethene
  参考文献：
  名称：

  Identification of novel SAR properties of the Jak2 small molecule inhibitor G6: Significance of the para-hydroxyl orientation

  摘要：

  In this study, we analyzed the structure-activity relationship properties of the small molecule Jak2 inhibitor G6. We synthesized a set of derivatives containing the native para-hydroxyl structure or an alternative meta-hydroxyl structure and examined their Jak2 inhibitory properties. We found that the para-hydroxyl derivative known as NB15 had excellent Jak2 inhibitory properties in silico, in vitro, and ex vivo when compared with meta-hydroxyl derivatives. These results indicate that NB15 is a potent derivative of the Jak2 inhibitor G6, and that maintaining the para-hydroxyl orientation of G6 is critical for its Jak2 inhibitory potential. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.042

文献信息

• Synthesis and Nematocidal Activity of Hydroxystilbenes
  作者：Mohammad Ahad ALI、Kaoru KONDO、Yoshisuke TSUDA

  DOI：10.1248/cpb.40.1130

  日期：1992.5.25

  Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed dy demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2, 6-dihydroxy-, 3, 4-dihydroxy-, 3, 5-dihydroxy-, 2, 2'-dihydroxy-, 3, 3'-dihydroxy-, 3, 4'-dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC)=30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.

  通过一种新的(Z)-(E)异构化方法随后进行脱甲基反应，从(E)/(Z)混合甲氧基二苯乙烯中合成了多种(E)-羟基二苯乙烯。当甲氧基二苯乙烯脱甲基生成羟基二苯乙烯时，表现出杀线虫活性。为了产生这种活性，C-2或C-3位置上必须有一个羟基。因此，2-羟基-、3-羟基-、2,6-二羟基-、3,4-二羟基-、3,5-二羟基-、2,2'-二羟基-、3,3'-二羟基-、3,4'-二羟基-、2-羟基-4-甲氧基-、5-羟基-2-甲氧基-、2-羟基-6-甲氧基-、6-烯丙氧基-2-羟基-、3-羟基-5-甲氧基-和5-烯丙氧基-3-羟基二苯乙烯表现出相当强的杀线虫活性。5-烯丙氧基-3-羟基二苯乙烯的活性最强[最小致死浓度（MLC）=30 μM]。(E)和(Z)异构体的活性相当。二氢衍生物，羟基联苄中也保留了这些活性，尽管较弱。
• Photochemical Properties of 3,3′-Disubstituted Stilbene Dendrimers
  作者：Kazumi Kato、Atsuya Momotake、Yoshihiro Shinohara、Tomoo Sato、Kayori Takahashi、Ritsuko Nagahata、Yoshinobu Nishimura、Tatsuo Arai

  DOI：10.1246/bcsj.82.603

  日期：2009.5.15

  The quantum yield of isomerization and the fluorescence lifetime of newly synthesized 3,3′-disubstituted water-soluble stilbene dendrimer trans-4 were significantly different from those of model compounds. The results indicate that not only properties of dendrimer surfaces but also substituent positions are important for dendrimer photochemistry.

  新合成的 3,3′-二取代水溶性链烯树枝状聚合物反式-4 的异构化量子产率和荧光寿命与模型化合物有显著差异。结果表明，不仅树枝状聚合物表面的特性，取代基的位置对树枝状聚合物的光化学也很重要。
• Ni(I)-Catalyzed Hydroxylation of Aryl Halides with Water under Thermal Catalysis
  作者：Liu Yang、Yonggang Yan、Ni Cao、Jing Hao、Gang Li、Wei Zhang、Rui Cao、Chao Wang、Jianliang Xiao、Dong Xue

  DOI：10.1021/acs.orglett.2c03840

  日期：2022.12.30

  A highly efficient hydroxylation of (hetero)aryl halides using water as a hydroxyl source via Ni catalysis promoted by PhSiH3 under thermal catalysis is reported. This methodology provides a general procedure to obtain diverse multifunctional pharmaceutically phenols and polyphenols, some of which are proven challenging to be synthesized using literature methods. Mechanism studies demonstrated that

  报道了在热催化下，通过 PhSiH 3促进的 Ni 催化，使用水作为羟基源对（杂）芳基卤化物进行高效羟基化。该方法提供了获得多种多功能药用酚和多酚的一般程序，其中一些已被证明难以使用文献方法合成。机理研究表明，添加 PhSiH 3会导致活性 Ni(I) 物质的产生，其通过 Ni(I)–Ni(III) 途径催化羟基化。
• Anti-proliferative composition
  申请人：Nutricia N.V.

  公开号：EP1314438A1

  公开（公告）日：2003-05-28

  Non-estrogen-dependent hyperproliferation of cells in animals or humans can be prevented or treated by means of a pharmaceutical or nutritional composition containing a combination of a) two or more inhibitors of the G1/S phase of the cell cycle; and b) two or more inhibitors of the G2/M phase of the cell cycle; and c) two or more inhibitors of protein tyrosine kinase activity. Especially, component a) comprises two or more compounds selected from flavanolignans, carotenoids and isoflavone; component b) comprises two or more compounds selected from flavanolignans, hydroxylated stilbenes, isoflavones and apigenin; and component c) comprises two or more compounds selected from flavanolignans and isoflavones.

  动物或人体内非雌激素依赖性细胞过度增殖可通过含有以下成分组合的药物或营养组合物来预防或治疗 a) 细胞周期 G1/S 期的两种或两种以上抑制剂；以及 b) 细胞周期 G2/M 期的两种或两种以上抑制剂；以及 c) 两种或两种以上蛋白酪氨酸激酶活性抑制剂。 特别是，成分 a) 包括两种或两种以上选自黄烷木质素、类胡萝卜素和异黄酮的化合物；成分 b) 包括两种或两种以上选自黄烷木质素、羟基化芪、异黄酮和芹菜素的化合物；成分 c) 包括两种或两种以上选自黄烷木质素和异黄酮的化合物。
• Low melting and low viscosity thermoset matrix resins from the Z configuration of polyhydroxy stilbenes
  申请人：The United States of America, as represented by the Secretary of the Navy

  公开号：US10723834B1

  公开（公告）日：2020-07-28

  The invention generally relates to novel poly-substituted cis stilbenes, their synthesis, their purification, and their use in thermoset resins. These novel cis stilbenes give rise to thermoset resins with greatly improved processing characteristics such as lower melting temperature and lower viscosity; resulting in polymers and composites having greatly improved thermal stability.

  本发明一般涉及新型多取代顺式二苯乙烯、其合成、纯化及其在热固性树脂中的应用。这些新型顺式二苯乙烯可产生热固性树脂，大大改善其加工特性，如降低熔化温度和粘度，从而使聚合物和复合材料的热稳定性大大提高。