6-(2,3-dimethoxy-phenyl)-1,2-dimethoxy-naphthalene | 109979-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(2,3-dimethoxy-phenyl)-1,2-dimethoxy-naphthalene
• 英文别名: 6-(2,3-Dimethoxy-phenyl)-1,2-dimethoxy-naphthalin；6-(2,3-Dimethoxyphenyl)-1,2-dimethoxynaphthalene
• CAS: 109979-71-7
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: PLPLKHUQYAADDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2,3-dimethoxy-phenyl)-1,2-dimethoxy-naphthalene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以54%的产率得到6-(2,3-dihydroxyphenyl)naphthalene-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：

  (2,3-二甲氧基苯基)乙醛 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 6-(2,3-dimethoxy-phenyl)-1,2-dimethoxy-naphthalene
  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

文献信息

• Facile access to methoxylated 2-phenylnaphthalenes and epoxydibenzocyclooctenes
  作者：Cédric Maurin、Fabrice Bailly、Philippe Cotelle

  DOI：10.1016/j.tet.2005.02.091

  日期：2005.7

  were treated with concentrated hydrochloric acid in 1,4-dioxane to give methoxylated 2-phenylnaphthalenes or 1,2,9,10-tetrahydro-1,9-epoxydibenzo[a,e]cyclooctenes. Yields in 2-phenylnaphthalenes were quite good and 1,2,9,10-tetrahydro-1,9-epoxydibenzo[a,e]cyclooctenes could be easily isolated. 2-Phenylnaphthalenes were obtained by a tandem aldol condensation-intramolecular Friedel–Crafts cyclisation

  在浓盐酸中在1,4-二恶烷中处理甲氧基化的苯乙醛，得到甲氧基化的2-苯基萘或1,2,9,10-四氢-1,9-环氧二苯并[ a，e ]环辛烯。2-苯基萘的收率相当好，并且可以容易地分离出1,2,9,10-四氢-1,9-环氧二苯并[ a，e ]环辛烯。通过串联的羟醛缩合-分子内Friedel-Crafts环化和1,2,9,10-四氢-1,9-环氧二苯并[ a，e ]环辛烯通过O缩合然后再进行两次分子内的Friedel-化，获得2-苯基萘。工艺品烷基化。
• Gopinath et al., Journal of the Chemical Society, 1957, p. 1144,1146
  作者：Gopinath 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.