α,β-dimethyl-γ-(3,4-dimethoxyphenyl) butyrolactone | 4676-42-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α,β-dimethyl-γ-(3,4-dimethoxyphenyl) butyrolactone
• 英文别名: α,β-Dimethyl-γ-<3,4-dimethoxy-phenyl>-butyrolacton；5-(3,4-dimethoxy-phenyl)-3,4-dimethyl-dihydro-furan-2-one；5-(3,4-Dimethoxy-phenyl)-3,4-dimethyl-dihydro-furan-2-on；5-(3,4-Dimethoxyphenyl)-3,4-dimethyloxolan-2-one；5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-one
• CAS: 4676-42-0
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: JYDFDDBNXLDYKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α,β-dimethyl-γ-(3,4-dimethoxyphenyl) butyrolactone 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 五氯化磷 作用下， 以 甲醇 、 苯 为溶剂， 反应 3.17h， 生成 (7S,7'R,8S,8'S)-3',4',4,5-tetramethoxy-2,7'-cyclolignan-7-ol
  参考文献：
  名称：

  Aryltetralols from Holostylis reniformis and syntheses of lignan analogous

  摘要：

  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.

  DOI：

  10.1016/j.phytol.2015.06.001
• 作为产物：
  描述：

  3,4-二甲氧基苯丙酮 在 硫酸 、 溶剂黄146 、 锌 作用下， 以 苯 为溶剂， 反应 9.0h， 生成 α,β-dimethyl-γ-(3,4-dimethoxyphenyl) butyrolactone
  参考文献：
  名称：

  Aryltetralols from Holostylis reniformis and syntheses of lignan analogous

  摘要：

  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.

  DOI：

  10.1016/j.phytol.2015.06.001

文献信息

• 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
• 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.