(E)-3,3',5,5'-tetrahydroxystilbene | 33626-09-4

• 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)-3,3',5,5'-tetrahydroxystilbene
• 英文别名: trans-3,3',5,5'-tetrahydroxystilbene；3,3',5,5'-tetrahydroxystilbene；5-[2-(3,5-dihydroxyphenyl)-(E)-1-ethenyl]-1,3-benzenediol；5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol
• CAS: 33626-09-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: NPUWPQJIMKMGDE-OWOJBTEDSA-N

物化性质

• 熔点：
  290 °C
• 沸点：
  521.6±30.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 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：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3,3',5,5'-tetrahydroxystilbene 在 sodium periodate 、 四氧化锇 、 三氟化硼乙醚 、 sodium hydride 、 potassium tri-sec-butyl-borohydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.5h， 生成 2,3-dihydro-5-(hydroxymethyl)-3-(hydroxymethylene)-2,2-dimethyl-7-(1-methyl-4-phenylbutoxy)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  六氢-6 H-二苯并[ b，d ]吡喃的合成：9-Nor-9β-羟基六氢大麻酚的衍生物

  摘要：

  为了评估大麻素中苯酚功能对于镇痛活性的重要性，制备了一系列新的9-nor-9β-羟基六氢大麻素。合成1 -取代的（H，CH 2 OH，OH，NH 2）6aβ，7,8,9,10,10a α -六氢- 9β羟基-6,6-二甲基-3- [1-甲基描述了来自3，5-二羟基sti，3，3′，5，5′-四羟基sti或1，3，5-三羟基苯的4-苯基丁氧基] -6 H-二苯并[ b，d ]吡喃。通过核磁共振和X射线晶体分析获得相对的立体化学和结构确认。

  DOI：

  10.1002/jhet.5570270312
• 作为产物：
  描述：

  3,5-diacetoxybenzyl-(triphenyl)phosphonium bromide 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (E)-3,3',5,5'-tetrahydroxystilbene
  参考文献：
  名称：

  Reimann,E., Justus Liebigs Annalen der Chemie, 1971, vol. 750, p. 109 - 127

  摘要：

  DOI：

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。
• Sun protection compositions comprising semi-crystalline polymers and hollow latex particles
  申请人：Candau Didier

  公开号：US20090041691A1

  公开（公告）日：2009-02-12

  Topically applicable cosmetic/dermatological UV protection compositions having enhanced SPF contain at least one organic UV screening agent and/or at least one inorganic screening agent, such compositions also containing at least the following constituents (A) and (B): A) a semi-crystalline polymer which is solid at ambient temperature and has a melting point of greater than or equal to 30° C., containing a) a polymeric backbone and b) at least one crystallizable organic side chain and/or one crystallizable organic block forming part of the backbone of this said polymer, said polymer having a number-average molecular mass Mn of greater than or equal to 1,000, and B) hollow latex particles having a particle size ranging from 150 to 380 nm, formulated into a topically applicable, physiologically acceptable medium therefor.

  具有增强SPF的适用于化妆品/皮肤科的防紫外线保护组合物至少包含一种有机紫外线过滤剂和/或至少一种无机过滤剂，此类组合物还至少包含以下成分（A）和（B）： A）半结晶聚合物，室温下为固体，熔点大于或等于30°C，包含a）聚合骨架和b）至少一种可结晶有机侧链和/或作为该聚合物骨架一部分的可结晶有机块，该聚合物具有大于或等于1,000的数均分子质量Mn，以及 B）中空乳胶颗粒，粒径范围为150至380纳米，配制成适用于局部使用的、生理上可接受的介质。
• 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。
• MOLECULARLY IMPRINTED POLYMERS
  申请人：Hearn Milton T. W.

  公开号：US20120052757A1

  公开（公告）日：2012-03-01

  The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.

  本发明提供了设计分子印迹聚合物（MIPs）的方法，这些方法在从各种生物加工原料和废弃物中提取生物活性化合物方面具有应用。本发明进一步针对由本发明方法设计的MIPs。
• Energy Transfer and<i>trans</i>–<i>cis</i>Isomerization in Dendrimer Aggregates
  作者：Yousuke Miura、Atsuya Momotake、Tomoo Sato、Yoko Kanna、Masaya Moriyama、Yoshinobu Nishimura、Tatsuo Arai

  DOI：10.1246/bcsj.20100318

  日期：2011.4.15

  Stilbene-cored dendrimers having benzophenone peripheries with alkyl chains formed 1 µm and 4 nm aggregates in methylcyclohexane (MCH) for trans-1 and trans-2, respectively. Even in the aggregates, trans-1 underwent efficient trans–cis photoisomerization from the excited triplet state produced via intramolecular two-step energy transfer.

  具有烷基链苯基酮外围的苯乙烯核心树枝状聚合物在甲基环己烷中分别形成了1 µm和4 nm的聚集体（trans-1和trans-2）。即使在聚集体中，trans-1也通过分子内两步能量转移，从激发的三重态有效地发生了反式-顺式光异构化。