6-methoxy-[1,1'-biphenyl]-3-ol | 13522-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methoxy-[1,1'-biphenyl]-3-ol
• 英文别名: 4-Methoxy-3-phenyl-phenol；6-Methoxybiphenyl-3-ol；4-methoxy-3-phenylphenol
• CAS: 13522-79-7
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: XZIMMDINMCPWLO-UHFFFAOYSA-N

物化性质

• 熔点：
  44-48 °C
• 沸点：
  343.5±30.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-[1,1'-biphenyl]-3-ol 在 碘苯二乙酸 作用下， 反应 1.33h， 生成 2-methoxy-3-phenyl-5,6,7,12-tetrahydrobenzo[2,3]azepino[4,5-b]indole
  参考文献：
  名称：

  通过布朗斯台德酸催化环化原位生成的二氢螺喹啉中间体合成氮杂吲哚和氧杂吲哚

  摘要：

  我们开发了一种简单有效的合成方案来生产 5,6,7,12-四氢苯并[2,3]氮杂[4,5- b ]吲哚和 7,12-二氢-6 H-苯并[2,3] oxepino[4,5- b ]吲哚衍生物在温和条件下。该成环过程涉及通过形成二氢螺吲哚喹啉（作为反应途径中的关键中间体）原位生成的酮亚胺部分的分子内环化。进行了一些对照实验和光谱研究以阐明潜在的反应机制。

  DOI：

  10.1021/acs.orglett.4c01091
• 作为产物：
  描述：

  5-Phenylazo-biphenyl-2-ol 在 palladium on activated charcoal 硫酸 、 氢气 、 sodium hydride 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 3.5h， 生成 6-methoxy-[1,1'-biphenyl]-3-ol
  参考文献：
  名称：

  2,3-Dihydrobenzofuran-2-ones: a new class of highly potent antiinflammatory agents

  摘要：

  A series of 2,3-dihydrobenzofuran-2-one analogues of the mold metabolite wortmannin, which is a powerful antiinflammatory compound, was synthesized. Most of these compounds were tested for their ability to inhibit the carrageenin paw edema and the adjuvant-induced arthritis of the rat and for their ability to inhibit prostaglandin synthesis in vitro. Indomethacin and diclofenac were used as references. The results show that compounds bearing an alkyl or aryl group in position 6 and an additional substituent, preferably chlorine, in position 5 are very powerful antiinflammatory agents and inhibitors of prostaglandin synthesis. The most active among these compounds, 5-chloro-6-cyclohexyl-2,3-dihydrobenzofuran-2-one, was significantly more potent than diclofenac in all testing models, more powerful than indomethacin in inhibiting acute inflammation and prostaglandin synthesis, and somewhat less potent than the latter compound in the adjuvant arthritis model.

  DOI：

  10.1021/jm00144a019

文献信息

• Electrochemical Cross‐Dehydrogenative Coupling between Phenols and β‐Dicarbonyl Compounds: Facile Construction of Benzofurans
  作者：Yandong Wang、Bailin Tian、Mengning Ding、Zhuangzhi Shi

  DOI：10.1002/chem.201904750

  日期：2020.4

  required to facilitate the dehydrogenation and dehydration processes. The key factor in the success was the use of n Bu 4 NBF 4 as the electrolyte and hexafluoroisopropanol (HFIP) as the solvent, which play key roles in the cyclocondensation step. This electrolysis is scalable and can be used as a key step in drug synthesis. On the basis of the several experimental results, the mechanism, particularly

  制备电化学合成是建立绿色可持续工艺的理想方法。与传统的化学合成方法相比，有机化学策略的主要优点是避免了试剂浪费和温和的反应条件。在此，已经开发了在不分开的电解条件下，酚与β-二羰基化合物之间的分子间交叉脱氢偶联（CDC），以构建各种苯并呋喃。过渡金属或外部化学氧化剂都不需要以促进脱氢和脱水过程。成功的关键因素是使用n Bu 4 NBF 4作为电解质，使用六氟异丙醇（HFIP）作为溶剂，它们在环缩合步骤中起关键作用。这种电解是可扩展的，可以用作药物合成中的关键步骤。
• Efficient Synthesis of Oxygenated Terphenyls and Other Oligomers: Sequential Arylation Reactions Through Phenol Oxidation-Rearomatization
  作者：Toshifumi Dohi、Tohru Kamitanaka、Shohei Watanabe、Yinjun Hu、Naohiko Washimi、Yasuyuki Kita

  DOI：10.1002/chem.201202086

  日期：2012.10.22

  One by one: Starting from simple phenols, a diverse series of oxygenated terphenyl compounds can be prepared in a concise and practical manner using sequential arylation reactions involving phenol oxidation/rearomatization and quinone monoacetal intermediates (see scheme). Many of the terphenyl products can be used for preparing well‐defined oligomers and, furthermore, contain valuable functional groups

  一个接一个：从简单的酚类开始，可以使用涉及酚氧化/再芳构化和醌单缩醛中间体的顺次芳基化反应，以简明而实用的方式制备一系列氧化的三联苯化合物（参见方案）。许多三联苯产品可用于制备定义明确的低聚物，此外，还包含有价值的官能团，可以对其进行转化以进一步多样化。
• Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products
  作者：David T. Smith、Edon Vitaku、Jon T. Njardarson

  DOI：10.1021/acs.orglett.7b01479

  日期：2017.7.7

  phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

  已经开发出一种温和的脱芳香化作用，可以用六氟乙酰丙酮（hfacac）取代基对芳香族C–H键进行邻位选择性取代。该反应取决于高碘生成的苯氧on中间体，关键溶剂的选择以及试剂的添加顺序。可以将氟化的二氢苯并呋喃产物转化为装饰有2-三氟甲基的二氢苯并呋喃和苯并呋喃产物。3-三氟甲基酰基取代的苯并呋喃迅速形成水合物，可以将其还原为相应的醇。
• Tuning the Reactivity of Peroxo Anhydrides for Aromatic C–H Bond Oxidation
  作者：Afsaneh Pilevar、Abolfazl Hosseini、Marina Šekutor、Heike Hausmann、Jonathan Becker、Kevin Turke、Peter R. Schreiner

  DOI：10.1021/acs.joc.8b01392

  日期：2018.9.7

  demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C–H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.

  从聚合物到药物，许多化学研究领域中的酚部分都是关键的结构基序。在此，我们报告了结构上苛刻的环状过氧化物（螺[双环[2.2.1]庚烷-2,4'-[1,2]二氧戊环] -3'，5'-二酮，P4）的设计和使用。芳族底物的直接羟基化。新的过氧化物具有高的热稳定性，可以由容易获得的起始原料合成。使用P4进行的芳族CH氧化通常显示出良好的产率（高达96％）和可观的区域选择性。
• Electrooxidative and Regioselective C−H Azolation of Phenol and Aniline Derivatives
  作者：Pengju Feng、Guojian Ma、Xiaoguang Chen、Xing Wu、Ling Lin、Peng Liu、Tianfeng Chen

  DOI：10.1002/anie.201901762

  日期：2019.6.17

  practical protocol was developed for the regioselective C−H azolation of phenol and aniline derivatives by electrooxidative cross‐coupling. The reaction occurs under metal‐, oxidant‐, and reagent‐free conditions, allowing access to a wide variety of synthetically useful heteroarene derivatives. The reaction also tolerates a broad range of functional groups and is amenable to gram‐scale synthesis. Finally

  通过电氧化交叉偶联，开发了一种通用且实用的方案，用于苯酚和苯胺衍生物的区域选择性CHH偶氮化。该反应在无金属，无氧化剂和无试剂的条件下发生，从而可以使用多种合成上有用的杂芳烃衍生物。该反应还可以耐受各种官能团，并且适用于克级合成。最后，初步的机理研究表明，自由基-自由基-结合途径可能参与了偶联反应。