9-(2-hydroxyphenyl)anthracene | 146746-37-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 9-(2-hydroxyphenyl)anthracene
• 英文别名: 2-(anthracen-9-yl)phenol；2-anthracen-9-ylphenol
• CAS: 146746-37-4
• 化学式: C₂₀H₁₄O
• 分子量: 270.331
• InChiKey: WBUYLCDLNQVTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• 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：

  9-(2-hydroxyphenyl)anthracene 在 sodium tetrahydroborate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 2-(9,10-dihydroanthracen-9-yl)phenol
  参考文献：
  名称：

  通过形式激发态分子内质子转移将水和醇光加成到 9-(2'-羟基苯基)蒽的蒽部分

  摘要：

  标题化合物通过蒽部分的 9- 和 10- 位有效地光加成一分子羟基溶剂（H（2）O、MeOH、（Me）（2）CHOH），得到可分离的三苯甲醇或三苯甲基醚类型产品。该反应被认为是通过一种涉及水介导的形式激发态分子内质子转移 (ESIPT) 从酚 OH 到蒽环的 10 位的机制进行的，产生一种邻醌甲基化物中间体，可通过纳秒激光闪光观察到光解，可被亲核试剂捕获。质子转移的“水中继”机制似乎是合理的，但无法直接用可用数据证明。在氘化溶剂中照射导致在光加成产物的亚甲基位置引入一个氘原子，和回收起始材料 10 位的部分氘交换，与提出的正式激发态质子转移机制一致。氘交换和光加成在大约 5 M 水（在 CH(3)CN 或 CH(3)OH 中）时达到最大量子效率，在没有羟基溶剂的情况下没有观察到反应，表明这种类型的 ESIPT 对溶剂组成。

  DOI：

  10.1021/ja039078g
• 作为产物：
  描述：

  9-溴蒽 在 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成 9-(2-hydroxyphenyl)anthracene
  参考文献：
  名称：

  含蒽基侧臂的新型铀酰-沙洛芬配合物的合成及光化学行为

  摘要：

  在本文中，我们报告了两种铀酰 - 沙罗酚受体的合成和物理化学研究，它们带有一个或两个附加到沙罗酚骨架的蒽基部分。尽管存在蒽基荧光团，但未检测到荧光发射。光物理数据和循环伏安实验表明，从蒽局部的第一单线激发态到金属中心的光诱导电子转移是强烈的，因此表明这是这些配合物的主要荧光猝灭机制。研究的化合物在紫外线照射下具有光反应性，根据特定的复合物和实验条件产生蒽光氧化或光二聚产物。

  DOI：

  10.1080/10610278.2012.752089

文献信息

• Formaldehyde-Extruding Homolytic Aromatic Substitution via C→O Transposition: Selective ‘Traceless-Linker’ access to Congested Biaryl Bonds
  作者：Pabhon Poonpatana、Gabriel dos Passos Gomes、Thomas Hurrle、Kimhoa Chardon、Stefan Bräse、Kye-Simeon Masters、Igor Alabugin

  DOI：10.1002/chem.201700085

  日期：2017.7.6

  A new, selective way to form C−C bonds has been developed. In this report, we disclose the homolytic aromatic substitution via C→O transposition coupled with the elimination of formaldehyde (as a traceless linker). Computational analysis indicates the selectivity can be tuned by sterics in the starting materials following an ipso‐attack that leads to the C→O transposition.

  已经开发出一种新的，选择性的形成C-C键的方法。在此报告中，我们公开了通过C→O换位以及甲醛消除（作为无痕连接子）进行的均质芳族取代。计算分析表明选择性可通过以下内容的在原料空间相互作用被调谐本位-attack该引线到C→O;换位。
• Direct Transformation of Esters into Arenes with 1,5-Bifunctional Organomagnesium Reagents
  作者：Achim Link、Christian Fischer、Christof Sparr

  DOI：10.1002/anie.201505414

  日期：2015.10.5

  A direct transformation of carboxylic acid esters into arenes with 1,5‐bifunctional organomagnesium reagents is described. This efficient and practical method enables the one‐step defunctionalization of various carboxylic acid esters to prepare benzene, anthracene, tetracene, and pentacene derivatives. A double nucleophilic addition of the 1,5‐organodimagnesium reagent to the ester is followed by an

  描述了使用1,5-双功能有机镁试剂将羧酸酯直接转化为芳烃的方法。这种高效实用的方法可以一步一步将各种羧酸酯进行去官能化反应，以制备苯，蒽，并四苯和并五苯衍生物。在酯中双亲核加成1,5-有机二镁试剂后，立即进行1,4-消除反应，导致新芳香环的直接[5 + 1]形成。
• Enhancement of antiproliferative activity by phototautomerization of anthrylphenols
  作者：Marijeta Kralj、Lidija Uzelac、Yu-Hsuan Wang、Peter Wan、Martina Tireli、Kata Mlinarić-Majerski、Ivo Piantanida、Nikola Basarić

  DOI：10.1039/c5pp00099h

  日期：2015.6

  An antiproliferative investigation was conducted on 3 human cancer cell lines, HCT 116 (colon), MCF-7 (breast), and H 460 (lung), on a series of 4 anthrylphenols in the dark and upon exposure to light (350 nm). 9-(2-Hydroxyphenyl)anthracene (1) moderately inhibited proliferation, but irradiation considerably enhanced the effect. The other anthracenes 4–6 exhibited antiproliferative activity in the dark, which was not enhanced upon irradiation. The enhancement of the antiproliferative effect on the irradiation of 1 was rationalized as being due to the formation of quinone methide (QM 2) by excited state proton transfer. QM 2 acts as an electrophilic species capable of reacting with biological molecules. Although QM 2 reacts with nucleotides, the adducts could not be isolated. On the contrary, cysteine adduct 8 was isolated and characterized, whereas the adducts with glycine, serine and tripeptide glutathione were characterized by MS. Non-covalent binding of 1 to DNA and bovine serum albumin was demonstrated by UV-vis, fluorescence and CD spectroscopy. However, a straightforward conclusion regarding the DNA or protein alkylating (damaging) ability of 2 could not be drawn. The results obtained by the irradiation of 1 in the presence of DNA, amino acids and peptides, cell cycle perturbation analysis, and in vitro translation of GFP suggest that the effect is not only due to the damage of DNA but also due to the impact on the cellular proteins. Considering that to date all QM agents were assumed to target DNA dominantly, this is an important finding with an impact on the further development of anticancer agents based on QMs.

  在黑暗中和光照（350 nm）下，对3个人类癌细胞系（HCT 116（结肠癌）、MCF-7（乳腺癌）和H 460（肺癌））进行了一系列4种蒽酚的抗增殖研究。9-(2-羟基苯基)蒽（1）适度抑制增殖，但辐照可显著增强其效果。其他蒽类化合物4-6在黑暗中表现出抗增殖活性，但辐照后效果并未增强。1的抗增殖效果在辐照后增强，这可以归因于激发态质子转移形成的醌甲烷（QM 2）。QM 2是一种亲电物质，能够与生物分子发生反应。虽然QM 2与核苷酸发生反应，但无法分离出加合物。相反，分离并鉴定了半胱氨酸加合物8，并通过质谱鉴定了与甘氨酸、丝氨酸和三肽谷胱甘肽的加合物。紫外-可见光、荧光和CD光谱法证明了1与DNA和牛血清白蛋白的非共价结合。然而，无法直接得出2对DNA或蛋白质烷基化（破坏）能力的结论。在DNA、氨基酸和肽存在的情况下辐照1、细胞周期扰动分析和GFP体外翻译获得的结果表明，这种效果不仅归因于DNA
• Rice, Joseph E.; Cai, Zhen-Wei, Tetrahedron Letters, 1992, vol. 33, # 13, p. 1663 - 1678
  作者：Rice, Joseph E.、Cai, Zhen-Wei

  DOI：——

  日期：——
• Stereoselective Alkali-Metal Catalysts for Highly Isotactic Poly(<i>rac</i>-lactide) Synthesis
  作者：Yangyang Sun、Jiao Xiong、Zhongran Dai、Xiaobo Pan、Ning Tang、Jincai Wu

  DOI：10.1021/acs.inorgchem.5b02709

  日期：2016.1.4

  A high degree of chain end control in the isoselective ring-opening polymerization (ROP) of rac-lactide is a challenging research goal. In this work, eight highly active sodium and potassium phenolates as highly isoselective catalysts for the ROP of rac-lactide are reported. The best isoselectivity value of P-m = 0.94 is achieved. The isoselective mechanism is chain-end control through the analysis of the stereoerrors in the microstructure of a final polymer; thus, isotactic multiblock structure polymers are obtained, and the highest melt point can reach 192.5 degrees C. The donating group in phenolate can clearly accelerate the ROP reaction, potassium complexes are more active than the analogous sodium complexes, and the big spacial hindrance of the ligand can decrease the activity. The high isoselectivities of these complexes mostly result from their sandwich structure constructed by the plane of the crown and the plane of the anthryl group.