2-(2,4-dimethoxyphenyl)naphthalene | 1271737-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2,4-dimethoxyphenyl)naphthalene
• 英文别名: 1-(2-naphthyl)-2,4-dimethoxybenzene
• CAS: 1271737-04-2
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: OIFBTDMJHYFBSA-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-(2,4-dimethoxyphenyl)naphthalene 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到4-(naphth-2-yl)-1,3-dihydroxybenzene
  参考文献：
  名称：

  Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues

  摘要：

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.028
• 作为产物：
  描述：

  萘-2-羰基萘-2-羧酸酯 、 2,4-二甲氧基苯硼酸 在 二氯化双(三环己基膦)镍(II) 、 caesium carbonate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以64%的产率得到2-(2,4-dimethoxyphenyl)naphthalene
  参考文献：
  名称：

  脱羰镍催化的芳基酸酐的铃木-宫浦交叉偶联合成联芳基

  摘要：

  过渡金属催化的交叉偶联已广泛用于合成化学中许多重要分子的合成，以构建各种C–C键。常规的交叉偶联反应需要活性的亲电子偶联伴侣，例如有机卤化物或磺酸盐，它们对环境不够友好。在本文中，我们公开了第一个镍催化的芳基酸酐和芳基硼酸的Suzuki-Miyaura交联，以脱羰基方式合成联芳基。在此过程中，该反应可耐受多种吸电子，中性电子和给电子性取代基。

  DOI：

  10.1021/acs.joc.0c02266

文献信息

• Synthesis of Biaryls via Decarbonylative Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling of Aryl Anhydrides
  作者：Jing-Ya Zhou、Rui-Qing Liu、Cheng-Yi Wang、Yong-Ming Zhu

  DOI：10.1021/acs.joc.0c02266

  日期：2020.11.6

  construction of diverse C–C bonds. Conventional cross-coupling reactions require active electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly enough. Herein, we disclose the first nickel-catalyzed Suzuki–Miyaura cross-coupling of aryl anhydrides and arylboronic acids for the synthesis of biaryls in a decarbonylation manner. The reaction tolerates a wide range

  过渡金属催化的交叉偶联已广泛用于合成化学中许多重要分子的合成，以构建各种C–C键。常规的交叉偶联反应需要活性的亲电子偶联伴侣，例如有机卤化物或磺酸盐，它们对环境不够友好。在本文中，我们公开了第一个镍催化的芳基酸酐和芳基硼酸的Suzuki-Miyaura交联，以脱羰基方式合成联芳基。在此过程中，该反应可耐受多种吸电子，中性电子和给电子性取代基。
• Structure-based design, synthesis and preliminary anti-inflammatory activity of bolinaquinone analogues
  作者：Carmen Petronzi、Rosanna Filosa、Antonella Peduto、Maria Chiara Monti、Luigi Margarucci、Antonio Massa、Simona Francesca Ercolino、Valentina Bizzarro、Luca Parente、Raffaele Riccio、Paolo de Caprariis

  DOI：10.1016/j.ejmech.2010.11.028

  日期：2011.2

  As a part of our drug discovery efforts we developed a series of simplified derivatives of bolinaquinone (BLQ), a hydroxyquinone marine metabolite, showing potent anti-inflammatory activity. Thirteen new hydroxyquinone derivatives closely related to BLQ were synthesized and tested on mouse macrophagelike RAW 264.7 cell line in order to investigate their ability to modulate the production of Prostaglandin E-2 (PGE(2)). This optimization process led to the identification of three strictly correlated compounds with comparable and higher inhibitory potency than BLQ on PGE2 production. To evaluate the affinity of BLQ and its analogues for h5PLA(2), surface plasmon resonance (SPR) experiments were performed. (C) 2010 Elsevier Masson SAS. All rights reserved.