3-(3,4,5-Trimethoxy-phenyl)-5,6,7-trimethoxy-naphthalin | 5320-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(3,4,5-Trimethoxy-phenyl)-5,6,7-trimethoxy-naphthalin
• 英文别名: 1,2,3-Trimethoxy-7-(3,4,5-trimethoxyphenyl)naphthalene
• CAS: 5320-36-5
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: HGKHSTXOENHPFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-Trimethoxy-phenyl)-5,6,7-trimethoxy-naphthalin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以75%的产率得到7-(3,4,5-trihydroxyphenyl)naphthalene-1,2,3-triol
  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：

  3,4,5-三甲氧基苯乙酸 生成 3-(3,4,5-Trimethoxy-phenyl)-5,6,7-trimethoxy-naphthalin
  参考文献：
  名称：

  基于生物遗传学理论的秋水仙碱的全合成

  摘要：

  描述了五步合成的去乙酰氨基多西奇碱（XLVI），其中环A和C通过对酮系统的氧化偶联而连接在一起。这样就完成了秋水仙碱（I）的生物遗传型全合成。

  DOI：

  10.1016/s0040-4020(01)96977-7

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。
• Organocatalytic Enantioselective Pictet–Spengler Approach to Biologically Relevant 1-Benzyl-1,2,3,4-Tetrahydroisoquinoline Alkaloids
  作者：Andrea Ruiz-Olalla、Martien A. Würdemann、Martin J. Wanner、Steen Ingemann、Jan H. van Maarseveen、Henk Hiemstra

  DOI：10.1021/acs.joc.5b00509

  日期：2015.5.15

  A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethyl-amines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst: (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.
• Total synthesis of colchicine modelled on a biogenetic theory
  作者：A.I. Scott、F. McCapra、R.L. Buchanan、A.C. Day、D.W. Young

  DOI：10.1016/s0040-4020(01)96977-7

  日期：1965.1

  A five step synthesis of desacetamidocolchiceine (XLVI) is described in which rings A and C are joined by oxidative coupling of the tropolone system. This completes a biogenetic-type total synthesis of colchicine (I).

  描述了五步合成的去乙酰氨基多西奇碱（XLVI），其中环A和C通过对酮系统的氧化偶联而连接在一起。这样就完成了秋水仙碱（I）的生物遗传型全合成。
• 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.