4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-3-(methoxymethyl)naphthalene-2-carbaldehyde | 79606-73-8

• 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: 4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-3-(methoxymethyl)naphthalene-2-carbaldehyde
• CAS: 79606-73-8
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: ZQIKNLLDXDBRDI-UHFFFAOYSA-N

物化性质

• 沸点：
  528.8±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,1'-[(2S,3S)-2,3-双(甲氧基甲基)-1,4-丁二基]双[3,4-二甲氧基苯] 在 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 0.67h， 以92%的产率得到4-(3,4-Dimethoxyphenyl)-6,7-dimethoxy-3-(methoxymethyl)naphthalene-2-carbaldehyde
  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

• Transformations of lignans, part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives
  作者：Revuru Venkateswarlu、Chakicherla Kamakshi、Syed G.A Moinuddin、Pithani V Subhash、Robert S Ward、Andrew Pelter、Michael B Hursthouse、Mark E Light

  DOI：10.1016/s0040-4020(99)00801-7

  日期：1999.11

  converted under various reaction conditions into a range of derivatives including the di- and tri-O-methyl ethers 10 and 11, a 3,4-dibenzyl-3-hydroxy-tetrahydrofuran 12, and its acetate 13. These derivatives undergo oxidative cyclisation with DDQ in acetic acid or trifluoroacetic acid to yield 1-aryltetralin, 1-arylnaphthalene, dibenzocyclooctadiene and spirodienone derivatives in reactions which provide biomimetic

  gmelinol的氢解8与钠在液氨中给出了一个三醇9，这是在各种反应条件下转化成范围衍生物包括二-和三- ø -甲基醚10和11，3,4-二苄基-3-羟基四氢呋喃12及其乙酸酯13。这些衍生物在乙酸或三氟乙酸中与DDQ进行氧化环化反应，在反应中生成1-芳基四氢萘，1-芳基萘，二苯并环辛二烯和螺二烯酮衍生物，这些反应为木脂素的生物遗传转化提供了仿生类似物。
• Oxidative aryl-aryl, aryl-benzyl coupling of lignans-reactions of phyllanthin and haloderivatives with ttfa, ddq, li/thf)))): synthesis of dibenzocyclooctadiene system and phyltetralin
  作者：Panchagnula Satyanarayana、Somepalli Venkateswarlu、Kamma N. Viswanatham

  DOI：10.1016/s0040-4020(01)91020-8

  日期：1991.9

  Treatment of phyllanthin (1) with TTFA in TFA gives dibenzocyclooctadiene (2) and phyltetralin (3). Treatment of (1) with DDQ in TFA also affords (2) while with DDQ in acetic acid gives 1-phenylnaphthalenic lignan (4). Synthesis of halophyllanthins (5,6,7) and its Ullmann reaction in ultrasonic condition affords reductive dehalogenated product (1) instead of (2). Treatment of (1) with POCl3 in TCA gives (+) 3,4-diveratryltetrahydrofuran (8) and its conversion to (9) also reported. Treatment of (5) with TTFA/TFA gives (9).
• Reactions of aryltetralin lignans with DDQ - an example of DDQ oxidation of an allylic ether group.
  作者：R.S. Ward、P. Satyanarayana、B.V.Gopala Rao

  DOI：10.1016/s0040-4039(01)81817-7

  日期：1981.1
• Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans
  作者：Kadali S Sagar、Chia-Chuan Chang、Wei-Kung Wang、Jung-Yaw Lin、Shoei-Sheng Lee

  DOI：10.1016/j.bmc.2004.05.036

  日期：2004.8

  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.