methyl 2,3-trimethoxyphenanthrene-9-carboxylate | 35675-93-5

• 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: methyl 2,3-trimethoxyphenanthrene-9-carboxylate
• 英文别名: methyl 2,3-dimethoxyphenanthrene-9-carboxylate；2,3-dimethoxy-phenanthrene-9-carboxylic acid methyl ester；2,3-Dimethoxy-phenanthren-9-carbonsaeure-methylester
• CAS: 35675-93-5
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: ONZSGFXVWHIJSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  methyl 2,3-trimethoxyphenanthrene-9-carboxylate 在 喹啉 、 甲醇 、 三溴化硼 、 铜 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 2,3-dihydroxyphenanthrene
  参考文献：
  名称：

  Synthesis and antioxidant activity of hydroxylated phenanthrenes as cis-restricted resveratrol analogues

  摘要：

  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.

  DOI：

  10.1016/j.foodchem.2012.05.074
• 作为产物：
  描述：

  (E)-3-(3,4-Dimethoxy-phenyl)-2-phenyl-acrylic acid methyl ester 在 三氯一氧化钒 三氯代氧化钒(V) 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以54%的产率得到methyl 2,3-trimethoxyphenanthrene-9-carboxylate
  参考文献：
  名称：

  三氯化钒 (VOCl3) 对芪的分子内联芳基氧化偶联：取代菲衍生物的简便合成

  摘要：

  摘要 三氯氧化钒 (VOCl3) 已被证明是富电子二苯乙烯分子内联芳基氧化偶联反应的高效试剂。因此，开发了一种从二苯乙烯氧化得到菲衍生物的温和有效的途径。

  DOI：

  10.1081/scc-120027245

文献信息

• Intramolecular Biaryl Oxidative Coupling of Stilbenes by Vanadium Oxytrichloride (VOCl₃): Facile Synthesis of Substituted Phenanthrene Derivatives
  作者：Zhong Jin、Qingmin Wang、Runqiu Huang

  DOI：10.1081/scc-120027245

  日期：2004.12.31

  Abstract Vanadium oxytrichloride (VOCl3) has proven to be a highly efficient reagent for intramolecular biaryl oxidative coupling reaction of electron‐rich stilbenes. Accordingly, a mild and efficient route to phenanthrene derivatives from stilbenes oxygenated is developed.

  摘要 三氯氧化钒 (VOCl3) 已被证明是富电子二苯乙烯分子内联芳基氧化偶联反应的高效试剂。因此，开发了一种从二苯乙烯氧化得到菲衍生物的温和有效的途径。
• Halton, Brian; Maidment, Andrew I.; Officer, David L., Australian Journal of Chemistry, 1984, vol. 37, # 26, p. 2119 - 2128
  作者：Halton, Brian、Maidment, Andrew I.、Officer, David L.、Warnes, Jeremy M.

  DOI：——

  日期：——
• Cook et al., Journal of the Chemical Society, 1954, p. 4234,4237
  作者：Cook et al.

  DOI：——

  日期：——
• HALTON, B.;MAIDMENT, A. I.;OFFICER, D. L.;WARNES, J. M., AUSTRAL. J. CHEM., 1984, 37, N 10, 2119-2128
  作者：HALTON, B.、MAIDMENT, A. I.、OFFICER, D. L.、WARNES, J. M.

  DOI：——

  日期：——
• 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.