2,6-二甲氧基-4-苯基苯酚 | 3687-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,6-二甲氧基-4-苯基苯酚
• 英文名称: aucuparin
• 英文别名: 3,5-dimethoxy-1,1'-biphenyl-4-ol；2,6-dimethoxy-4-phenylphenol；3,5-dimethoxybiphenyl-4-ol
• CAS: 3687-28-3
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: KCKBEANTNJGRCV-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C
• 沸点：
  349.4±37.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  2,6-二甲氧基-4-苯基苯酚 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以45%的产率得到noraucuparin
  参考文献：
  名称：

  Biosynthesis of the biphenyl phytoalexin aucuparin in Sorbus aucuparia cell cultures treated with Venturia inaequalis

  摘要：

  Aucuparin is the most widely distributed biphenyl phytoalexin in the rosaceous subtribe Pyrinae, which includes the economically important fruit trees apple and pear. The biphenyl scaffold is formed by biphenyl synthase, which catalyzes biosynthesis of 3,5-dihydroxybiphenyl. Conversion of this precursor to aucuparin (3,5-dimethoxy-4-hydroxybiphenyl) was studied in cell cultures of Sorbus aucuparia after treatment with an elicitor preparation from the scab-causing fungus Venturia inaequalis. The sequence of the biosynthetic steps detected was O-methylation - 4-hydroxylation - O-methylation. The two alkylation reactions were catalyzed by distinct methyltransferases, which differed in pH and temperature optima as well as stability. Biphenyl 4-hydroxylase was a microsomal cytochrome P450 monooxygenase, whose activity was appreciably decreased by the addition of established P450 inhibitors. When fed to V. inaequalis-treated S. aucuparia cell cultures, radioactively labeled 3,5-dihydroxybiphenyl was not only incorporated into aucuparin but also into the dibenzofuran eriobofuran, the accumulation of which paralleled that of aucuparin. However, biphenyl 2'-hydroxylase activity proposed to be involved in dibenzofuran formation was detected in neither microsomes nor cell-free extracts in the presence of NADPH and 2-oxoglutarate, respectively. Nevertheless, a basis for studying biphenyl biosynthesis at the gene level is provided. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.003
• 作为产物：
  描述：

  1,3-二甲氧基-5-苯基苯 生成 2,6-二甲氧基-4-苯基苯酚
  参考文献：
  名称：

  Nilsson,M.; Norin,T., Acta Chemica Scandinavica (1947), 1963, vol. 17, # 4, p. 1157 - 1159

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Regioselective Synthesis of Oxygenated Biphenyls
  作者：Santhosh Chittimalla、Rajesh Kuppusamy、Naresh Akavaram

  DOI：10.1055/s-0034-1379987

  日期：——

  Michael addition reaction of arylboronic acids to cyclohexa-2,4-dienones followed by aromatization sequence in one-pot furnished several oxygenated biphenyl derivatives. Application of the developed methodology was successfully applied to the synthesis of biphenyl natural products aucuparin and 2′-hydroxy-3,4,5-trimethoxybiphenyl.

  钯催化剂介导的芳基硼酸与环六-2,4-二烯酮的迈克尔加成反应，然后在一锅中进行芳构化序列，提供了几种氧化联苯衍生物。所开发方法的应用已成功应用于联苯天然产物金盏花素和2'-羟基-3,4,5-三甲氧基联苯的合成。
• First Enantioselective Synthesis of Surinamensinol B and a Non-Natural Polysphorin Analogue by a Two-Stereocentered Hydrolytic Kinetic Resolution
  作者：Komal G. Lalwani、Arumugam Sudalai

  DOI：10.1002/ejoc.201501009

  日期：2015.11

  An efficient and economical approach to the synthesis of antitumor and anti-inflammatory surinamensinol B (1) and antimalarial polysphorin analogue 2 has been achieved with high enantiomeric purity (96 % ee) by starting from commercially available 3,4,5-trimethoxybenzaldehyde. The key steps of the strategy include a Co-catalyzed two-stereocentered hydrolytic kinetic resolution (HKR) of racemic 2-[(methoxymethoxy)(3

  通过从市售的 3,4,5-三甲氧基苯甲醛开始，以高对映体纯度 (96% ee) 实现了一种高效且经济的合成抗肿瘤和抗炎 surinamensinol B (1) 和抗疟疾 polysphorin 类似物 2 的方法。该策略的关键步骤包括外消旋 2-[(甲氧基甲氧基)(3,4,5-三甲氧基苯基)甲基]环氧乙烷 (13) 的共催化双立体中心水解动力学拆分 (HKR) 作为手性诱导步骤，然后是三信反应。手性环氧化物 14 和手性二醇 15 用于两种化合物的合成。
• Inclusion abilities towards hexyne isomers by co-crystallization with extended V-shaped host molecule
  作者：Masatoshi Kawahata、Masahide Tominaga、Kousuke Fujimaru、Tadashi Hyodo、Kentaro Yamaguchi

  DOI：10.1016/j.tet.2019.130576

  日期：2019.10

  Disubstituted adamantane derivative possessing chloropyrazine (1) was synthesized and used as an extended V-shaped host molecule for the preparation of inclusion crystals containing hexyne isomers. The crystallization of 1 with 3-hexyne or 2-hexyne in chloroform provided co-crystals (1a, 1b) with 1:2 host:guest complexation stoichiometry, whereas guest-free crystals (1c) were produced in the case of 1-hexyne

  合成了具有氯吡嗪（1）的双取代金刚烷衍生物，并将其用作扩展的V形主体分子，用于制备含有己炔异构体的包裹体晶体。的结晶1与3-己炔或在氯仿提供共结晶2-己炔（1A，1B与1）：2主机：客人络合的化学计量，而自由客体-晶体（1C在1-己炔的情况下被生产） 。在共晶体中，从1到CH···O相互作用建立的二聚体通过多个分子间相互作用排列成分子网络，并且客体分子被容纳在由1个四个分子构成的腔体内。从3-己炔或2-己炔和在存在1-己炔等摩尔二元混合物的结晶1，共晶体1A和1B分别供给，分别。竞争实验表明，对己炔异构体的选择性为1，依次为3-己炔和2-己炔≫ 1-己炔。
• Natural phytoalexins inspired the discovery of new biphenyls as potent antifungal agents for treatment of invasive fungal infections
  作者：Jian-Chuan Liu、Jian Yang、Shu-Xin Lei、Ming-Fan Wang、Yan-Ni Ma、Rui Yang

  DOI：10.1016/j.ejmech.2023.115842

  日期：2023.12

  discovering novel and effective antifungal agents derived from natural sources, a series of new biphenyls based on natural biphenyl phytoalexins were designed, synthesized and evaluated for their antifungal activities against four invasive fungi. By modifying the two benzene rings of noraucuparin, a well-known biphenyl phytoantitoxin, some promising compounds with remarkable antifungal activity were discovered

  为了发现源自天然来源的新颖有效的抗真菌剂，设计、合成了一系列基于天然联苯植物抗毒素的新型联苯，并评估了其对四种入侵真菌的抗真菌活性通过修饰去核桃苷（一种著名的联苯植物抗毒素）的两个苯环，发现了一些具有显着抗真菌活性的有前景的化合物。值得注意的是，化合物23a、23e和23h表现出有效的活性和广泛的抗真菌谱，MIC 低至0.25-16 μg/mL，比先导化合物去核桃苷的效力强 8-256 倍。特别是，它们对新型隐球菌表现出与阳性对照两性霉素 B 相当的效力。还讨论了一些有趣的结构-活性关系。初步机理研究表明，化合物23h可能通过破坏真菌细胞膜来实现其快速杀菌活性。此外，化合物23h新型隐球菌的部分毒力因子具有显着的抑制作用，对正常人体细胞毒性低，具有良好的药代动力学和类药特性。上述结果证明，从天然植物抗毒素中开发新的抗真菌候选药物是一个光明且有前途的策略。
• Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae
  作者：Bernd Schmidt、Martin Riemer

  DOI：10.1021/jo500675a

  日期：2014.5.2

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.