1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene | 5811-91-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene
• 英文别名: 1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalin；Dehydroguajacharzsaeure-dimethylaether；6,7-Dimethoxy-2,3-dimethyl-1-(3,4-dimethoxy-phenyl)-naphthalin；Dehydro-guaiarsaeure-dimethylether；Dehydroguaiaretsaeuredimethylether；Dehydro-dimethylguaiaretigsaeure；1-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-2,3-dimethylnaphthalene
• CAS: 5811-91-6
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: UCIBBODKLVDMBY-UHFFFAOYSA-N

物化性质

• 熔点：
  177-178 °C
• 沸点：
  454.7±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene 在 吡啶盐酸盐 作用下， 反应 0.5h， 以57%的产率得到5-(3,4-Dihydroxy-phenyl)-6,7-dimethyl-naphthalene-2,3-diol
  参考文献：
  名称：

  Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans

  摘要：

  Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepared from phyllanthin (1) for evaluation of anti-HIV activities. Anti-HIV activity of these compounds on a R5 pseudotype virus, ConB/pNL43E-L+, in the U87-CD4-CCR5 cells has been measured. Compounds 5, 22, 23, and 28 showed good anti-HIV activity with IC50 value of 0.25, 1.07, 0.01, 0.32 mug/mL, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.036
• 作为产物：
  描述：

  4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-3-(methoxymethyl)naphthalene-2-carbaldehyde 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 以92%的产率得到1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2,3-dimethyl-naphthalene
  参考文献：
  名称：

  Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans

  摘要：

  Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepared from phyllanthin (1) for evaluation of anti-HIV activities. Anti-HIV activity of these compounds on a R5 pseudotype virus, ConB/pNL43E-L+, in the U87-CD4-CCR5 cells has been measured. Compounds 5, 22, 23, and 28 showed good anti-HIV activity with IC50 value of 0.25, 1.07, 0.01, 0.32 mug/mL, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.036

文献信息

• Lignans from Machilus edulis
  作者：P.L. Majumder、A. Chatterjee、G.C. Sengupta

  DOI：10.1016/0031-9422(72)80053-0

  日期：1972.2

  Abstract (+)-Guaiacin, a trans(2,3)-trans(3,4) phenyltetralin lignan, has been isolated for the first time from the stem bark of Machilus edulis King (Lauraceae) together with dihydroguaiaretic acid. Contrary to earlier observations, (+)-guaiacin has been converted by two different routes to (+)-galbulin, a new optical antipode of (−)-galbulin. Physical properties including NMR and MS data as well

  摘要 (+)-Guaiacin 是一种反式(2,3)-反式(3,4) 苯基四氢化萘木脂素，首次与二氢愈创木酸一起从樟科植物的茎皮中分离得到。与早期的观察相反，(+)-愈创木酚已通过两种不同的途径转化为 (+)-galbulin，一种新的 (-)-galbulin 光学对映体。首次报道了这些木脂素的物理性质，包括 NMR 和 MS 数据以及化学降解反应。
• 311. The constituents of guaiacum resin. Part II. Synthesis of dl-guaiaretic acid dimethyl ether
  作者：Robert D. Haworth、Cecil R. Mavin、George Sheldrick

  DOI：10.1039/jr9340001423

  日期：——
• DIMERIC PROPENYL PHENOL ETHERS. XV. THE SYNTHESIS OF 1-VERATRYL-2,3-DIMETHYL-6,7-DIMETHOXYTETRALIN
  作者：ALEXANDER MÜLLER、MIKLÓS VAJDA

  DOI：10.1021/jo01140a002

  日期：1952.6
• Traverso,G., Gazzetta Chimica Italiana, 1960, vol. 90, p. 792 - 807
  作者：Traverso,G.

  DOI：——

  日期：——
• Schroeter; Lichtenstadt; Irineu, Chemische Berichte, 1918, vol. 51, p. 1600
  作者：Schroeter、Lichtenstadt、Irineu

  DOI：——

  日期：——