1,2-dimethoxy-6-phenylnaphthalene | 109253-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-dimethoxy-6-phenylnaphthalene
• 英文别名: 6-phenyl-1,2-dimethoxynaphthalene；1,2-dimethoxy-6-phenyl-naphthalene；1,2-Dimethoxy-6-phenyl-naphthalin
• CAS: 109253-84-1
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: MUEXUICCHXWPTA-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：

  1,2-dimethoxy-6-phenylnaphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到6-phenylnaphthalene-1,2-diol
  参考文献：
  名称：

  New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase—Discovery of a new polyhydroxylated antiviral agent

  摘要：

  A series of 13 hydroxylated 2-arylnaphthalenes have been synthesized and evaluated as HIV-1 integrase inhibitors. 7-(3,4,5-Trihydroxyphenyl) naphthalene-1,2,3-triol 1c revealed chemical instability upon storage, leading to the isolation of a dimer 5c which was also tested. In the 2-arylnaphthalene series, all compounds were active against HIV-1 IN with IC50' s within the 1-10 lM range, except for 1c and 5c which displayed submicromolar activity. Antiviral activity against HIV-1 replication was measured on 1b-c and 5c. Amongst the tested molecules, only 5c was found to present antiviral properties with a low cytotoxicity on two different cell lines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.059
• 作为产物：
  描述：

  N,N-dimethyl-3,4-dimethoxybenzylamine 在 potassium cyanide 、 正丁基锂 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 1,2-dimethoxy-6-phenylnaphthalene
  参考文献：
  名称：

  Mali; Jagtap; Borse, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 116 - 120

  摘要：

  DOI：

文献信息

• An Efficient Synthesis of Polysubstituted Naphthalene Derivatives by Gold-Catalyzed Cyclization of 1-Arylalka-2,3-dienyl Acetates
  作者：Wangqing Kong、Chunling Fu、Shengming Ma

  DOI：10.1002/ejoc.201001112

  日期：2010.12

  An efficient synthetic strategy to generate differently polysubstituted naphthalenes and iodonaphthalenes through a gold-catalyzed cyclization reaction of 1-arylalka-2,3-dienyl acetates was described. Due to the substituent loading capability of both the aromatic ring and the allene moiety, different substituents may be introduced to the different locations of the naphthalenes. A possible mechanism

  描述了一种有效的合成策略，通过 1-arylalk-2,3-二烯乙酸酯的金催化环化反应生成不同多取代的萘​​和碘代萘。由于芳环和丙二烯部分的取代基负载能力，不同的取代基可被引入到萘的不同位置。在机理研究的基础上提出了涉及形成烯基和萘基金物种的反应的可能机制。金物种的碘化提供了碘代萘，这是通过偶联反应引入分子复杂性和多样性的有用构建块。
• Cooke et al., Australian Journal of Chemistry, 1958, vol. 11, p. 230,233
  作者：Cooke et al.

  DOI：——

  日期：——
• New 2-arylnaphthalenediols and triol inhibitors of HIV-1 integrase—Discovery of a new polyhydroxylated antiviral agent
  作者：Cédric Maurin、Cédric Lion、Fabrice Bailly、Nadia Touati、Hervé Vezin、Gladys Mbemba、Jean François Mouscadet、Zeger Debyser、Myriam Witvrouw、Philippe Cotelle

  DOI：10.1016/j.bmc.2010.05.059

  日期：2010.7

  A series of 13 hydroxylated 2-arylnaphthalenes have been synthesized and evaluated as HIV-1 integrase inhibitors. 7-(3,4,5-Trihydroxyphenyl) naphthalene-1,2,3-triol 1c revealed chemical instability upon storage, leading to the isolation of a dimer 5c which was also tested. In the 2-arylnaphthalene series, all compounds were active against HIV-1 IN with IC50' s within the 1-10 lM range, except for 1c and 5c which displayed submicromolar activity. Antiviral activity against HIV-1 replication was measured on 1b-c and 5c. Amongst the tested molecules, only 5c was found to present antiviral properties with a low cytotoxicity on two different cell lines. (C) 2010 Elsevier Ltd. All rights reserved.
• Mali; Jagtap; Borse, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 2, p. 116 - 120
  作者：Mali、Jagtap、Borse

  DOI：——

  日期：——