2-(3,4-dimethoxyphenyl)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3,4-dimethoxyphenyl)naphthalene
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: ZLYTXZHCQGTPRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)naphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以62%的产率得到4-(naphthalen-2-yl)benzene-1,2-diol
  参考文献：
  名称：

  具有体内功效的新型抗炎剂功能化4-芳基-儿茶酚衍生物的设计与合成

  摘要：

  氧化应激和炎症是许多多因素疾病中共存的两种情况，抗氧化剂的发现是一种有吸引力的方法，可以同时解决花生四烯酸级联的两个或多个治疗靶点。 我们报告说，支架的 4-芳基-苯-1,2-二醇侧臂上的简单结构变化显着影响对 5-LOX与12- 和 15-LOX 的选择性。使用 DPPH 和铁离子降低抗氧化能力 (FRAP) 方法评估了衍生物4 al的抗氧化活性。对接模拟提出了儿茶酚系列与 5-LO 的具体结合。选定的活性化合物4-(3,4-二羟基苯基)二苯并呋喃 ( 4l)也在不同的体内炎症小鼠模型中进行了测试。 4l （0.1 mg/kg；腹膜内注射）（I）乙酰胆碱激发的卵清蛋白致敏小鼠的支气管收缩受损，（II）角叉菜胶诱导的爪水肿中渗出物的形成，以及（III）酵母聚糖诱导的气袋中的白细胞浸润。这些结果为研究 4-芳基-苯-1,2-二醇作为新型多靶点治疗药物的治疗潜力铺平了道路，能够调节复杂的炎症级联机制。

  DOI：

  10.1016/j.ejmech.2022.114788
• 作为产物：
  描述：

  2-萘甲腈 、 2-(3,4-dimethoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane 在 copper (II)-fluoride 、 二氯化双(三环己基膦)镍(II) 、 potassium tert-butylate 、 三环己基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以60%的产率得到2-(3,4-dimethoxyphenyl)naphthalene
  参考文献：
  名称：

  Carbon−Carbon Formation via Ni-Catalyzed Suzuki−Miyaura Coupling through C−CN Bond Cleavage of Aryl Nitrile

  摘要：

  The Suzuki-Miyaura coupling of aryl nitriles with aryl/alkenyl boronic esters is reported. With this method, the cyano group could be applied as a protecting group of arenes and finally as a leaving group to further construct polyaryl scaffolds.

  DOI：

  10.1021/ol901217m

文献信息

• Mono- and dinuclear cyclopalladates as catalysts for Suzuki–Miyaura cross-coupling reactions in predominantly aqueous media
  作者：G. Narendra Babu、Samudranil Pal

  DOI：10.1016/j.tetlet.2017.01.089

  日期：2017.3

  Suzuki–Miyaura cross-coupling reactions of aryl halides with arylboronic acids were performed in predominantly aqueous media employing two mono- and two dinuclear cyclopalladated complexes as catalysts. These complexes are [Pd(HL)Cl] (I), [Pd(L)(PPh3)] (II), [Pd2(μ-dppb)(L)2] (III) and [Pd2(μ-dppf)(L)2] (IV); where H2L, dppb and dppf represent 4-methoxy-N′-(mesitylidene)benzohydrazide, 1,4-bis(dip

  芳基卤化物与芳基硼酸的Suzuki-Miyaura交叉偶联反应主要在水性介质中进行，使用两个单核和两个双核环钯配合物作为催化剂。这些络合物为[Pd（HL）Cl]（I），[Pd（L）（PPh 3）]（II），[Pd 2（μ- dppb）（L）2 ]（III）和[Pd 2（μ -dppf）（L）2 ]（IV）；其中H 2 L，dppb和dppf代表4-甲氧基-N′-（间亚甲基）苯甲酰肼，1，4-双（二苯基膦基）丁烷和1，1′-双（二苯基膦基）二茂铁。反应是在四丁基溴化铵（TBAB）存在下，以碳酸钾为碱，在二甲基甲酰胺-水（1:20）混合物中，于70/90°C下进行的。在所用的四种催化剂中，双核络合物IV证明是最有效的，并提供了中等至优异的收率，具有广泛的底物范围。
• Very Fast Suzuki-Miyaura Reaction Catalyzed by Pd(OAc)2 under Aerobic Conditions at Room Temperature in EGME/H2O
  作者：Alessandro Del Zotto、Francesco Amoroso、Walter Baratta、Pierluigi Rigo

  DOI：10.1002/ejoc.200800874

  日期：——

  The results of a ligand-free Pd(OAc)2-catalyzed Suzuki–Miyaura C–C coupling performed at room temperature under aerobic conditions are presented. It was found that the use of an ethylene glycol monomethyl ether/H2O mixture as the solvent resulted in very rapid reactions of aryl bromides with arylboronic acids. As a matter of fact, under optimized conditions, some substrates were converted quantitatively

  展示了在室温下在有氧条件下进行的无配体 Pd(OAc)2 催化的 Suzuki-Miyaura C-C 偶联的结果。发现使用乙二醇单甲醚/H 2 O混合物作为溶剂导致芳基溴化物与芳基硼酸的非常快速的反应。事实上，在优化的条件下，一些底物在不到 1 分钟的时间内被定量转化，具有极高的 TOF 值。例如，4-甲氧基苯基硼酸和溴苯之间的反应在 30 秒内得到 4-甲氧基联苯，TOF = 180000 h-1。此外，该反应耐受广泛的官能团，可成功应用于杂芳基溴化物，如 2-溴吡啶和 5-溴嘧啶。有趣的是，
• Bio-organometallic Organosulfur Chemistry. Transi- tion Metal-Catalyzed Cross-Coupling Using Coen- zyme M or Thioglycolic Acid as the Leaving Group
  作者：Jiri Srogl、Wansheng Liu、Daniel Marshall、Lanny S. Liebeskind

  DOI：10.1021/ja991654e

  日期：1999.10.1
• Scaffold hopping and optimisation of 3’,4’-dihydroxyphenyl- containing thienopyrimidinones: synthesis of quinazolinone derivatives as novel allosteric inhibitors of HIV-1 reverse transcriptase-associated ribonuclease H
  作者：Graziella Tocco、Francesca Esposito、Pierluigi Caboni、Antonio Laus、John A. Beutler、Jennifer A. Wilson、Angela Corona、Stuart F. J. Le Grice、Enzo Tramontano

  DOI：10.1080/14756366.2020.1835884

  日期：2020.1.1

  Bioisosteric replacement and scaffold hopping are powerful strategies in drug design useful for rationally modifying a hit compound towards novel lead therapeutic agents. Recently, we reported a series of thienopyrimidinones that compromise dynamics at the p66/p51 HIV-1 reverse transcriptase (RT)-associated Ribonuclease H (RNase H) dimer interface, thereby allosterically interrupting catalysis by altering the active site geometry. Although they exhibited good submicromolar activity, the isosteric replacement of the thiophene ring, a potential toxicophore, is warranted. Thus, in this article, the most active 2-(3,4-dihydroxyphenyl)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one 1 was selected as the hit scaffold and several isosteric substitutions of the thiophene ring were performed. A novel series of highly active RNase H allosteric quinazolinone inhibitors was thus obtained. To determine their target selectivity, they were tested against RT-associated RNA-dependent DNA polymerase (RDDP) and integrase (IN). Interestingly, none of the compounds were particularly active on (RDDP) but many displayed micromolar to submicromolar activity against IN.
• Carbon−Carbon Formation via Ni-Catalyzed Suzuki−Miyaura Coupling through C−CN Bond Cleavage of Aryl Nitrile
  作者：Da-Gang Yu、Miao Yu、Bing-Tao Guan、Bi-Jie Li、Yang Zheng、Zhen-Hua Wu、Zhang-Jie Shi

  DOI：10.1021/ol901217m

  日期：2009.8.6

  The Suzuki-Miyaura coupling of aryl nitriles with aryl/alkenyl boronic esters is reported. With this method, the cyano group could be applied as a protecting group of arenes and finally as a leaving group to further construct polyaryl scaffolds.