2,4,6-trimethoxyphenanthrene | 63366-84-7

• 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: 2,4,6-trimethoxyphenanthrene
• 英文别名: 2,4,6-Trimethoxy-phenanthren
• CAS: 63366-84-7
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: SLEILPOCCHXPTR-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  449.5±25.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-trimethoxyphenanthrene 在 甲醇 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 47.0h， 生成 2,4,6-trihydroxyphenanthrene
  参考文献：
  名称：

  Theoretical and experimental exploration of the photochemistry of resveratrol: beyond the simple double bond isomerization

  摘要：

  resveratrol的光化学异构化过程是近期研究的主题，其中报告了相互矛盾的结果。这一反应的光产物混合物需要被认为比顺反异构体的共存更为复杂。尽管其性质未知，但在不同研究中已检测到至少一种未鉴定的第三种产物。在这项工作中，我们的目标是通过实验和计算方法的协同结合，对这一反应的光化学过程进行详尽的描述。

  DOI：

  10.1039/c2ob26241j
• 作为产物：
  描述：

  3,4',5-三甲氧基-反-二苯代乙烯 在 air 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以37%的产率得到2,4,6-trimethoxyphenanthrene
  参考文献：
  名称：

  Theoretical and experimental exploration of the photochemistry of resveratrol: beyond the simple double bond isomerization

  摘要：

  resveratrol的光化学异构化过程是近期研究的主题，其中报告了相互矛盾的结果。这一反应的光产物混合物需要被认为比顺反异构体的共存更为复杂。尽管其性质未知，但在不同研究中已检测到至少一种未鉴定的第三种产物。在这项工作中，我们的目标是通过实验和计算方法的协同结合，对这一反应的光化学过程进行详尽的描述。

  DOI：

  10.1039/c2ob26241j

文献信息

• Effects of orchinol and related phenanthrenes on the enzymic degradation of indole-3-acetic acid
  作者：Tsung T. Lee、Gerald L. Rock、Albert Stoessl

  DOI：10.1016/s0031-9422(00)88680-x

  日期：1978.1

  Abstract Orchinol, hircinol, loroglossol and certain related phenanthrenes inhibited horseradish peroxidase-catalysed IAA degradation to a varied degree. Among

  摘要 Orchinol、hircinol、loroglossol 和某些相关的菲在不同程度上抑制辣根过氧化物酶催化的 IAA 降解。之中
• Welkstoffe und Antibiotika. 29. Mitteilung. Synthese von 2,4-Dimethoxy-6-hydroxy-9, 10-dihydrophenanthren
  作者：E. Hardegger、N. Rigassi、J. Seres、Ch. Egli、P. Müller、K. O. Fitzi

  DOI：10.1002/hlca.19630460710

  日期：——

  4-Dimethoxy-7-hydroxy-9,10-dihydrophenanthren) bezeichneten, induzierten Abwehrstoff erkrankter Knollen von Orchis militaris und dem biologisch inaktiven Loroglossol (wahrscheinlich 2,4-Dimethoxy-5-hydroxy-9,10-dihydrophenanthren) aus erkrankten Knollen von Loroglossum hircinum nahe und ist deshalb für biologische Versuche von Interesse.

  2,4-二甲氧基-6-羟基-9,10-二氢菲咯啉（XIX）酯结构化合物Orchinol（2,4-二甲氧基-7-羟基-9,10-二氢菲咯啉）bezeichneten，induzierten Abwehrstoff erkrankter Knollen von Orchis militaris und死于罗洛糖醇（wahrscheinlich 2,4-Dimethoxy-5-hydroxy-9,10-dihydrophenanthren）的抗药性和生物杀灭力。
• The photochemistry of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethyl ethanoate in alcohol solvents: A search for carbocation rearrangements
  作者：J C Roberts、J A Pincock

  DOI：10.1139/v03-072

  日期：2003.6.1

  The photochemistry of the title compound 1 in methanol and 2,2,2-trifluoroethanol has been examined. In both solvents two ether products were obtained: one (18) resulting from trapping of the carbocation 2 (expected from photosolvolysis of 1), and the other (19) from the carbocation 3 (expected after rearrangement by hydride migration of cation 2). The substituted trans- and cis-stilbene derivatives 20 and 21 were also primary photoproducts. Analysis of product yields as a function of time revealed that the ether product 19 was formed by secondary photolysis of the stilbene derivatives, presumably by a pathway involving excited state protonation. Nanosecond laser flash photolysis results demonstrated that substituted trans-stilbene 20 was produced on the same time scale as the laser pulse.Key words: ester photochemistry, stilbene photoadditions, carbocation rearrangements.

  标题化合物1在甲醇和2,2,2-三氟乙醇中的光化学性质已经被研究。在两种溶剂中，都得到了两种醚产物：一种（18）是由于捕获了碳阳离子2（从1的光溶解预期而来），另一种（19）是由于碳阳离子3（在阳离子2的氢迁移重排后预期而来）而产生的。取代的反-和顺-苯乙烯衍生物20和21也是主要的光产物。随着时间的推移，对产物产率的分析表明，醚产物19是通过反式-苯乙烯衍生物的二次光解产生的，可能是通过涉及激发态质子化的途径。纳秒激光脉冲光解实验结果表明，取代的反式-苯乙烯20在与激光脉冲相同的时间尺度上产生。关键词：酯光化学，苯乙烯光加成，碳阳离子重排。
• 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.
• The anisotropic effect of 4-substituents on the1H NMR chemical shift of H-5 in phenanthrenes
  作者：R. M. Letcher

  DOI：10.1002/mrc.1270160311

  日期：1981.7

  AbstractChloro‐, methoxy‐ and methyl‐substituents in the 4‐position of phenanthrenes exert a profound and diagnostic influence on the 1H chemicalshift of H‐5, and from 13C measurements it is considered to be dueto an anisotropic effect.