4-[(E)-2-(naphthalen-2-yl)ethenyl]phenol

• 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: 4-[(E)-2-(naphthalen-2-yl)ethenyl]phenol
• 英文别名: 4-[(E)-2-(2-naphthyl)vinyl]phenol；4-[(E)-2-naphthalen-2-ylethenyl]phenol
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: PZFXCZNGKMGDQQ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-[(E)-2-(naphthalen-2-yl)ethenyl]phenol 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 18.0h， 生成 (E)-N,N,N-triethyl-2-(4-(2-(naphthalen-2-yl)vinyl)-phenoxy)ethan-1-aminium iodide
  参考文献：
  名称：

  Subnanomolar Affinity and Selective Antagonism at α7 Nicotinic Receptor by Combined Modifications of 2-Triethylammonium Ethyl Ether of 4-Stilbenol (MG624)

  摘要：

  DOI：

  10.1021/acs.jmedchem.2c01256
• 作为产物：
  描述：

  2-萘甲醇 在 氢氧化钾 、 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 苯 为溶剂， 反应 0.5h， 生成 4-[(E)-2-(naphthalen-2-yl)ethenyl]phenol
  参考文献：
  名称：

  Further Naphthylcombretastatins. An Investigation on the Role of the Naphthalene Moiety

  摘要：

  By synthesis and biological studies of new naphthalene analogues of combretastatins, we have found that the naphthalene is a good surrogate for the isovanillin moiety (3-hydroxy-4methoxyphenyl) of combretastatin A-4, always generating highly cytotoxic analogues when combined with the 3,4,5-trimethoxyphenyl or related systems. On the other hand, when the naphthalene replaces the 3,4,5-trimethoxyphenyl moiety, the cytotoxic activity is largely decreased. The most cytotoxic naphthalene analogues of combretastatins, which also produce inhibition of tubulin polymerization, exerted their antimitotic effects through microtubule network disruption and subsequent G(2)/M arrest of the cell cycle in human cancer cells.

  DOI：

  10.1021/jm0310737

文献信息

• Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C═C Bond Cleavage
  作者：Yi Peng、Yan-Hui Fan、Si-Yuan Li、Bin Li、Jing Xue、Qing-Hai Deng

  DOI：10.1021/acs.orglett.9b03160

  日期：2019.10.18

  C═C bond breaking to access the C═N bond remains an underdeveloped area. A new protocol for C═C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for

  打破C bondC债券以获取C═N债券的领域仍然不发达。报道了一种在非氧化条件下通过4-羟基苯乙烯与芳基叠氮化物的铁催化的腈转移反应产生亚胺的烯烃的C═C键裂解的新方案。各种顺序一锅法反应的成功表明，该方法的良好兼容性使其对于合成应用非常有吸引力。在实验观察的基础上，还提出了合理的反应机理。
• Synthesis and cytotoxic effects on pancreatic cancer cells of resveratrol analogs
  作者：Barbara De Filippis、Laura De Lellis、Rosalba Florio、Alessandra Ammazzalorso、Pasquale Amoia、Marialuigia Fantacuzzi、Letizia Giampietro、Cristina Maccallini、Rosa Amoroso、Serena Veschi、Alessandro Cama

  DOI：10.1007/s00044-019-02351-3

  日期：2019.7

  pancreatic cancer cell lines were evaluated. The new molecules were designed by removing the 3- and 5-OH groups of resveratrol, and by incorporating other substituents in 4-position, or by replacing the dihydroxybenzene with other aromatic systems. In all compounds the 4′-OH was kept unalterated. The effects of the compounds on cell viability were analyzed in three pancreatic cancer cell lines with

  在这项研究中，合成了一系列白藜芦醇类似物，并评估了其对胰腺癌细胞系活力的影响。通过除去白藜芦醇的3-和5-OH基团，并通过在4-位引入其他取代基，或通过用其他芳族体系取代二羟基苯来设计新分子。在所有化合物中，4'-OH均保持不变。在三种具有不同遗传特征的胰腺癌细胞系中分析了这些化合物对细胞活力的影响。几种化合物（例如，5，9，和12相比于参比化合物）显示出改善的细胞毒活性，使得它们是进一步评估作为抗癌药物的潜在候选。
• PPARα agonists based on stilbene and its bioisosteres: biological evaluation and docking studies
  作者：Barbara De Filippis、Mariangela Agamennone、Alessandra Ammazzalorso、Isabella Bruno、Alessandra D'Angelo、Mauro Di Matteo、Marialuigia Fantacuzzi、Letizia Giampietro、Antonella Giancristofaro、Cristina Maccallini、Rosa Amoroso

  DOI：10.1039/c5md00151j

  日期：——

  A new series of gemfibrozil analogues conjugated with trans-stilbene were synthesized and evaluated with the aim of developing new PPARα agonists. The phenyls of stilbene were modified by introducing substituents in the ortho or para position and only the distal ring was substituted with naphthyl or heteroaromatic moieties, keeping the dimethylpentanoic skeleton of gemfibrozil unaltered. Two compounds

  为了开发新的PPARα激动剂，合成并评估了一系列新的与反式-二苯乙烯缀合的吉非贝齐类似物。通过在邻位或对位引入取代基来修饰二苯乙烯的苯基，并且仅远端环被萘基或杂芳族部分取代，从而保持了吉非贝齐的二甲基戊酸骨架不变。两种化合物5a和5d表现出良好的PPARα活化作用，还筛选了它们对PPARα调控的基因CPT1A的活性。对活性配体进行的基于结构的研究突出了配体溶剂化能和疏水效应在确定PPARα活化中的主导作用。
• Palladium-Catalyzed Dehydrative Heck Olefination of Secondary Aryl Alcohols in Ionic Liquids: Towards a Waste-Free Strategy for Tandem Synthesis of Stilbenoids
  作者：Rakesh Kumar、Amit Shard、Richa Bharti、Yogesh Thopate、Arun Kumar Sinha

  DOI：10.1002/anie.201107261

  日期：2012.3.12

  All in one: A tandem strategy has been developed wherein secondary aryl alcohols are directly coupled with aryl halides to provide stilbenoids through a dehydrative Heck sequence in the ionic liquid [hmim]Br, and with water as a by‐product under microwave irradiation (see scheme). Classical methods do not permit this sequence to proceed in one pot, and some methods require multiple steps. hmim=1‐n

  总而言之：已开发了一种串联策略，其中仲芳基醇直接与芳基卤化物偶合，以通过离子液体[hmim] Br中的脱水Heck序列提供二苯乙烯类化合物，并在微波辐射下与水作为副产物（参见方案）。经典方法不允许此序列在一个锅中进行，并且某些方法需要多个步骤。hmim = 1 - n-己基-3-甲基咪唑鎓。
• 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。