2-methoxy-3-hydroxyphenanthrene | 854908-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-methoxy-3-hydroxyphenanthrene
• 英文别名: Methyl-(3-hydroxy-phenanthryl-(2))-aether；3-Hydroxy-2-methoxy-phenanthren；2-Methoxy-[3]phenanthrol
• CAS: 854908-39-7
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: MGCUCIGLJPPKNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-methoxy-3-hydroxyphenanthrene 、 硫酸二甲酯 在 氢氧化钾 、 丙酮 作用下， 生成 2,3-dimethoxyphenanthrene
  参考文献：
  名称：

  Reaction of Some Substituted Phenanthrenes with n-Butyllithium

  摘要：

  DOI：

  10.1021/ja01867a054
• 作为产物：
  描述：

  3-acetoxy-2-methoxy-9,10-dihydro-phenanthrene 在 马来酸酐 、 sodium hydroxide 、 乙醇 、 钯 作用下， 生成 2-methoxy-3-hydroxyphenanthrene
  参考文献：
  名称：

  339.高香草醛

  摘要：

  DOI：

  10.1039/jr9470001692

文献信息

• Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues
  作者：De-Jun Ding、Xiao-Yan Cao、Fang Dai、Xiu-Zhuang Li、Guo-Yun Liu、Dong Lin、Xing Fu、Xiao-Ling Jin、Bo Zhou

  DOI：10.1016/j.foodchem.2012.05.074

  日期：2012.12

  Five hydroxylated phenanthrenes as "cis-configuration-fixed" resveratrol analogues differing in the number and position of the hydroxyl groups were designed and synthesized. Their antioxidant activity was studied by ferric reducing antioxidant power, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, and DNA strand breakage-inhibiting assays, corresponding to their electron-donating, hydrogen-transfer and DNA-protecting abilities, respectively. In the above assays, their activity depends significantly on the number and position of the hydroxyl groups, and most of them are more effective than resveratrol. Noticeably, compound 9b (2,4,6-trihydroxyl phenanthrene) with the same hydroxyl group substitutions as resveratrol, is superior to the reference compound, highlighting the importance of extension of the conjugation over multiple aromatic-rings. Similar activity sequences were obtained in different experimental models, but the appreciable differences could contribute detailed insights into antioxidant mechanisms. Based on these results, the hydroxylated phenanthrenes may be considered as a novel type of resveratrol-directed antioxidants. (C) 2012 Elsevier Ltd. All rights reserved.
• Reaction of Some Substituted Phenanthrenes with n-Butyllithium
  作者：Henry Gilman、Thomas H. Cook

  DOI：10.1021/ja01867a054

  日期：1940.10
• 339. Homovanillin
  作者：A. A. L. Challis、G. R. Clemo

  DOI：10.1039/jr9470001692

  日期：——