2-(3-(3,4-dimethoxyphenyl)-3-oxopropyl)-3,5-dimethoxycyclohexa-2,5-diene-1,4-dione | 1243268-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-(3,4-dimethoxyphenyl)-3-oxopropyl)-3,5-dimethoxycyclohexa-2,5-diene-1,4-dione
• 英文别名: evelynin A；evelynin；2-[3-(3,4-dimethoxyphenyl)-3-oxopropyl]-3,5-dimethoxycyclohexa-2,5-diene-1,4-dione
• CAS: 1243268-35-0
• 化学式: C₁₉H₂₀O₇
• 分子量: 360.364
• InChiKey: RESAUZHVVYGGHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基苯甲酸甲酯 在 dipotassium peroxodisulfate 、 titanium(IV)isopropoxide 、 silver nitrate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成 2-(3-(3,4-dimethoxyphenyl)-3-oxopropyl)-3,5-dimethoxycyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  γ-Carbonyl Quinones: Radical Strategy for the Synthesis of Evelynin and Its Analogues by C–H Activation of Quinones Using Cyclopropanols

  摘要：

  Cyclopropanols, on oxidative ring opening with AgNO3-K2S2O8 in DCM-H2O at room temperature and under open flask conditions, produced beta-keto radicals which were successfully added to quinones to furnish gamma-carbonyl quinones. This mild method has been applied to the synthesis of cytotoxic natural products, 4,6-dimethoxy-2,5-quinodihydrochalcone and evelynin.

  DOI：

  10.1021/ol402229m

文献信息

• Evelynin, a Cytotoxic Benzoquinone-Type <i>retro</i>-Dihydrochalcone from <i>Tacca chantrieri</i>
  作者：Jiangnan Peng、Evelyn M. Jackson、David J. Babinski、April L. Risinger、Gregory Helms、Doug E. Frantz、Susan L. Mooberry

  DOI：10.1021/np100350s

  日期：2010.9.24

  A new benzoquinone-type retro-dihydrochalcone, named evelynin, was isolated from the roots and rhizomes of Tacca chantrieri. The structure was elucidated on the basis of the analysis of spectroscopic data and confirmed by a simple one-step total synthesis. Evelynin exhibited cytotoxicity against four human cancer cell lines, MDA-MB-435 melanoma, MDA-MB-231 breast, PC-3 prostate, and HeLa cervical carcinoma cells, with IC50 values of 4.1, 3.9, 4.7, and 6.3 mu M, respectively.