3-[2-(4-羟基苯基)乙基]苯酚 | 37116-80-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 3-[2-(4-羟基苯基)乙基]苯酚
• 英文名称: lunularin
• 英文别名: 3-(4-hydroxyphenethyl)phenol；3-[2-(4-hydroxyphenyl)ethyl]phenol
• CAS: 37116-80-6
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: ILEYXPCRQKRNIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2907299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-[2-(4-羟基苯基)乙基]苯酚 在 37-kDA peroxidase from Marchantia polymorpha 、 双氧水 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 生成 perrottetin E
  参考文献：
  名称：

  A 37-kDa peroxidase secreted from liverworts in response to chemical stress

  摘要：

  A peroxidase was purified from the culture medium of a suspension culture of Marchantia polymorpha (liverwort) after treatment with bornyl acetate, which acts as a chemical stress agent to the cells. The peroxidase was characterised as a glycoprotein of molecular mass 37-kDa having a pl of about 10 and an optimal pH of 6.5. The peroxidase was thermally stable at 50 degreesC for up to 60 min. The partial amino acid sequence of the peroxidase was determined and found to be dissimilar to the amino acid sequences of other higher plant peroxidases. The oxidative polymerization of lunularin by this peroxidase was examined and the formation of a dimer, a trimer. and a tetramer was demonstrated by negative ion Fast Atom Bombardment (FAB)-mass spectroscopy of the reaction products. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(00)00262-4
• 作为产物：
  描述：

  半月苔酸 生成 3-[2-(4-羟基苯基)乙基]苯酚
  参考文献：
  名称：

  Asahina; Asano, Chemische Berichte, 1930, vol. 63, p. 429,435

  摘要：

  DOI：

文献信息

• Moosinhaltsstoffe—XVIII
  作者：S. Huneck

  DOI：10.1016/0040-4020(76)80029-4

  日期：1976.1

  2-Hydroxy-3,4′-dimethoxybibenzyl (=pellepiphyllin) and 3,4′-dihydroxybibenzyl (=lunularin) have been synthesized by Wittig type reactions. Condensation of 2,3-dimethoxybenzaldehyde with 4-methoxybenzylphosphonate to 2,3,4′ trimethoxystibene, catalytic reduction to 2,3,4′-trimethoxybibenzyl, demethylation to 2,3,4′-trihydroxybibenzyl and partial methylation yields pellepiphyllin. Lunularin was synthesized

  通过Wittig型反应合成了2-羟基-3,4'-二甲氧基联苄基（=叶绿素）和3,4'-二羟基联苄基（lunulain）。2,3-二甲氧基苯甲醛与4-甲氧基苄基膦酸酯缩合为2,3,4'-三甲氧基sti，催化还原为2,3,4'-三甲氧基联苄，脱甲基为2,3,4'-三羟基联苄和部分甲基化产生蝶草素。通过使3-甲氧基苯甲醛与4-甲氧基苄基膦酸酯反应成3,4'-二甲氧基,，催化氢化成3,4'-二甲氧基联苄，并用三溴化硼脱甲基，来合成Lunularin。
• 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。
• Chromium–Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols
  作者：Shota Nagasawa、Shogo Fujiki、Yusuke Sasano、Yoshiharu Iwabuchi

  DOI：10.1021/acs.joc.1c00438

  日期：2021.5.7

  aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium–salen (Cr–salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

  我们描述了使用由铬-salen（Cr-salen）配合物与硝酰基自由基组成的催化体系，使束缚酚的需氧分子内脱芳香反应。这种新颖的催化系统能够在温和的反应条件下有效地形成各种螺环二烯酮产物，包括那些以前报道的方法无法有效利用的产物。
• Short microwave-assisted modular synthesis of naturally occurring oxygenated bibenzyls
  作者：Jürgen Krauss、Ursula Kopp、Franz Bracher

  DOI：10.1515/znb-2015-0047

  日期：2015.9.1

  The naturally occurring oxygenated bibenzyls lunularin and m-O-methyllunularin were prepared in a modular synthesis in four steps from two appropriate iodophenols and trimethylsilylacetylene utilizing microwave-assisted Sonogashira couplings as the crucial steps. The antimicrobial activity of the resulting natural products was evaluated in an agar diffusion assay.

  天然存在的氧化双苯基化合物月形素和m-O-甲基月形素通过模块化合成从两种适当的碘酚和三甲基硅基乙炔经微波辅助Sonogashira偶联反应，共进行了四步制备。评估了所得天然产物的抗菌活性，采用琼脂扩散法进行了评估。

• (S)-2-hydroxycuparene [p-(1,2,2-trimethylcyclopentyl)-o-cresol] and 3,4′-ethylenebisphenol from a liverwort, Marchantia polymorpha linn
  作者：Barrie J. Hopkins、Guido W. Perold

  DOI：10.1039/p19740000032

  日期：——

  (S)-2-Hydroxycuparene and 3,4′-ethylenebisphenol have been isolated from Marchantia polymorpha Linn., together with a mixture of campesterol, stigmasterol, and β-sitosterol, and other terpenoid constituents. Syntheses of (R)-2-hydroxycuparene and of the bisphenol are reported.

  （S）-2-羟基cuparene和3,4'-亚乙基双酚已从多形马氏酵母中分离，并与菜油甾醇，豆甾醇和β-谷甾醇以及其他萜类成分混合。报道了（R）-2-羟基cuparene和双酚的合成。