4-oxogalbulin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 4-oxogalbulin
• 英文别名: 4α-(3,4-dimethoxyphenyl)-2α,3β-dimethyl-6,7-dimethoxy-1-tetralone；(±)-8,8’-epi-aristoligone；4c-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-2r,3t-dimethyl-3,4-dihydro-2H-naphthalen-1-one；4c-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-2r,3t-dimethyl-3,4-dihydro-2H-naphthalin-1-on；(2R,3S,4R)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: UCHGPGXURWMCBZ-SQHYZVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-oxogalbulin 在 palladium on activated charcoal 氢气 作用下， 生成 1β-(3,4-dimethoxyphenyl)-2β,3α-dimethyl-6,7-dimethoxytetralin
  参考文献：
  名称：

  含CrO 3和新木脂素合成的新试剂系统

  摘要：

  通过新的试剂系统CrO 3 –HBF 4 –MeCN或CrO 3 –HCIO 4 –MeCN氧化1-芳基丙-1-烯，得到4-芳基四离子（1a）和（1c），以及四氢呋喃（3），是芳基四氢萘和四氢呋喃新木脂素的前体分子。

  DOI：

  10.1039/c39830000098
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酮 在 三氯化铝 、 锌 、 苯 作用下， 生成 4-oxogalbulin
  参考文献：
  名称：

  DIMERIC PROPENYL PHENOL ETHERS. XV. THE SYNTHESIS OF 1-VERATRYL-2,3-DIMETHYL-6,7-DIMETHOXYTETRALIN

  摘要：

  DOI：

  10.1021/jo01140a002

文献信息

• Studies on Chromium Trioxide-Based Oxidative Coupling Reagents and Synthesis of Lignan-Cagayanone.
  作者：Yueh-Hsiung KUO、Sheng-Tsair LIN

  DOI：10.1248/cpb.41.1507

  日期：——

  Oxidation of 1-arylprop-1-enes by using the reagent system CrO3-HClO4-CH3CN at 0-5°C gave seven products from methyl isoeugenol, five from ethyl isoeugenol, four from benzyl isoeugenol, and five from isosafrole. Cagayanone was obtained from isosafrole in one step. The structures of the products were elucidated and the mechanism of their formation is discussed.

  在0-5°C下，使用CrO3-HClO4-CH3CN试剂体系对1-芳基丙-1-烯进行氧化，从甲基异丁香酚中得到了七种产物，从乙基异丁香酚中得到了五种，从苄基异丁香酚中得到了四种，从异香豆素中得到了五种。Cagayanone通过一步反应从异香豆素中获得。对产物的结构进行了阐明，并讨论了其形成机制。
• Collective synthesis of several 2,7′-cyclolignans and their correlation by chemical transformations
  作者：Yu Peng、Zhen-Biao Luo、Jian-Jian Zhang、Long Luo、Ya-Wen Wang

  DOI：10.1039/c3ob41672k

  日期：——

  Collective synthesis of anti-malarial 2,7′-cyclolignans has been stereoselectively achieved employing (±)-cyclogalgravin (2) as a linchpin through a series of functional group conversions, including redox reactions. Interestingly, 2 can be correlated with the neolignan (±)-kadangustin J (1) isolated from a different plant source, through a highly efficient dehydrative cyclization reaction with excellent

  通过一系列官能团转化（包括氧化还原反应），利用（±）-环没食子糖蛋白（2）作为关键物质，已经立体选择性地实现了抗疟疾2,7'-环木脂素的集体合成。有趣的是，通过高效的脱水环化反应以及藜芦基团的出色的非对映异构性分化和伴随的C1-C7键构建，可以将2与从不同植物来源分离得到的新木脂素（±）-kadangustin J（1）相关联。值得注意的是，stereodivergent的第一全合成（±）-8,8'-外延-aristoligone（5），（±）-8'-外延-aristoligone（7），（±）-8'-外延证实了-8-OH-马兜铃酮（8）和（±）-8'- epi-马兜铃酚（9）。
• New reagent system containing CrO3 and syntheses of neo-lignans
  作者：Tetsuya Takeya、Eiichi Kotani、Seisho Tobinaga

  DOI：10.1039/c39830000098

  日期：——

  Oxidations of 1-arylprop-1-enes by the new reagent systems, CrO3–HBF4–MeCN or CrO3–HCIO4–MeCN gave the 4-aryltetraiones (1a) and (1c), and the tetrahydrofuran (3) which are precursor molecules for aryltetrahydronaphthalene and tetrahydrofuran neo-lignans.

  通过新的试剂系统CrO 3 –HBF 4 –MeCN或CrO 3 –HCIO 4 –MeCN氧化1-芳基丙-1-烯，得到4-芳基四离子（1a）和（1c），以及四氢呋喃（3），是芳基四氢萘和四氢呋喃新木脂素的前体分子。
• Aryltetralols from Holostylis reniformis and syntheses of lignan analogous
  作者：Marcos D.P. Pereira、Matheus R. Ferreira、Gisele B. Messiano、Isabela Penna Cerávolo、Lucia M.X. Lopes、Antoniana U. Krettli

  DOI：10.1016/j.phytol.2015.06.001

  日期：2015.9

  Two new lignans, an aryltetralol and its methyl ether analogous, were isolated from Holostylis reniformis (Aristolochiaceae) together with futokadsurin C and (-)-8'-epi-aristoligone. The latter was also obtained as an enantiomeric mixture by synthesis and was transformed into aryltetralols and aryltetralenes that were subjected to chiral-HPLC separations. The compound structures were determined by spectroscopic methods. Several of these lignans had their antiplasmodial activity (against Plasmodium falciparum, W2 clone, anti-HRPII) and toxicity to mammalian kidney cells (MDL50) evaluated. (-)-Cyclogalgravin and (-)-aristoligol exhibited activity (IC50 similar to 10.8 and 8.4 mu M, respectively), the latter exhibited lower toxicity. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
• LIU, JIA-SEN;TAO, YONG;HUANG, MEI-FEN, ACTA CHIM. SIN., 46,(1988) N 5, 483-488
  作者：LIU, JIA-SEN、TAO, YONG、HUANG, MEI-FEN

  DOI：——

  日期：——