3,6-dimethoxyphenanthrene | 15638-08-1

• 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: 3,6-dimethoxyphenanthrene
• 英文别名: 3,6-dimethoxyphenathrene；3,6-dimethoxy-phenanthrene；3,6-Dimethoxy-phenanthren；3,6-Dimethoxyphenanthren；3.6-Dimethoxyphenanthren；Thebaol
• CAS: 15638-08-1
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: FSOLYWGGLXQAMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  3,6-dimethoxyphenanthrene 在 铬酸 、 溶剂黄146 作用下， 生成 3,6-dimethoxy-9,10-phenanthrenequinone
  参考文献：
  名称：

  Fieser, Journal of the American Chemical Society, 1929, vol. 51, p. 2468

  摘要：

  DOI：
• 作为产物：
  描述：

  (6-methoxy-[3]phenanthryl)-carbamic acid ethyl ester 生成 3,6-dimethoxyphenanthrene
  参考文献：
  名称：

  Studies in the Phenanthrene Series. VII. 3-Hydroxyacetylphenanthrenes and Amino Ketones and Alcohols Derived from Them. Hydroxyaminophenanthrenes¹

  摘要：

  DOI：

  10.1021/ja01323a028

文献信息

• New diformyldihydroxyaromatic precursors for luminescent Schiff base macrocycles: Synthesis, characterization, and condensation studies
  作者：Britta N Boden、Amir Abdolmaleki、Cecily T.-Z Ma、Mark J MacLachlan

  DOI：10.1139/v07-136

  日期：2008.1.1

  With the goal of preparing luminescent, fully conjugated Schiff base macrocycles, a series of precursors based on benzene, phenanthrene, and triphenylene with formylhydroxy functionalization have been prepared and characterized. The condensation of these compounds with substituted phenylenediamines to afford conjugated [2+2] or [3+3] Schiff base macrocycle has been investigated. Although the [3+3] Schiff base macrocycles could not be isolated, two new soluble and luminescent [2+2] Schiff base macrocycles with N₂O₂ binding pockets have been prepared and characterized.Key words: Schiff base, macrocycle, condensation, salicylaldehyde, conjugated.

  为了制备发光的全共轭席夫碱大环，我们制备了一系列基于苯、菲和三亚苯的甲酰羟基官能团前体，并对其进行了表征。研究人员研究了这些化合物与取代的苯二胺缩合生成共轭 [2+2] 或 [3+3] 席夫碱大环的过程。虽然未能分离出[3+3] 希夫碱大环，但制备出了两种新的可溶性发光[2+2] 希夫碱大环，并对其进行了表征：希夫碱 大环 缩合 水杨醛 共轭
• Preparation of Phenanthrenes by Photocyclization of Stilbenes Containing a Tosyl Group on the Central Double Bond. A Versatile Approach to the Synthesis of Phenanthrenes and Phenanthrenoids
  作者：Ana G. Neo、Carmen López、Victor Romero、Berta Antelo、José Delamano、Antonio Pérez、Dolores Fernández、Jesús F. Almeida、Luis Castedo、Gabriel Tojo

  DOI：10.1021/jo100742e

  日期：2010.10.15

  modification of the classical preparation of phenanthrenes by UV irradiation of stilbenes in the presence of an oxidant. This modification involves the irradiation, in the presence of base, of stilbenes possessing a sulfonyl group linked to the central double bond. We have proved that this protocol can be successfully applied for the synthesis of diverse phenanthrenes and phenanthrenoids.

  我们已经通过在氧化剂存在下紫外线照射对苯二酚对菲的经典制备方法进行了有用的修饰。该修饰涉及在碱的存在下辐照具有连接至中心双键的磺酰基的丁二烯。我们已经证明，该协议可以成功地应用于各种菲和菲类化合物的合成。
• Base-Induced Photocyclization of 1,2-Diaryl-1-tosylethenes. A Mechanistically Novel Approach to Phenanthrenes and Phenanthrenoids
  作者：Jesús F. Almeida、Luis Castedo、Dolores Fernández、Ana G. Neo、Víctor Romero、Gabriel Tojo

  DOI：10.1021/ol0357954

  日期：2003.12.1

  phenanthrenes and heterocyclic analogues. These results are consistent with a mechanism involving the base-induced elimination of p-toluenesulfinic acid from an intermediate 9-tosyl-4a,4b-dihydrophenanthrene, formed by photochemical cyclization of the starting 1,2-diaryl-1-tosylstilbenes. [reaction: see text]

  在碱的存在下，用紫外光照射许多1,2-二芳基-1-甲苯磺基苯甲酸酯，得到相应的菲和杂环类似物。这些结果与一种机理有关，该机理涉及从中间体9-甲苯基-4a，4b-二氢菲中碱诱导的对甲苯磺酸的消除，该中间体是通过对起始的1,2-二芳基-1-甲苯磺基苯进行光化学环化而形成的。[反应：看文字]
• Photooxygenation of aromatic alkenes in zeolite nanocavities
  作者：Masanobu Kojima、Miyuki Nakajoh、Chie Matsubara、Shuichi Hashimoto

  DOI：10.1039/b205672k

  日期：2002.10.30

  Aromatic alkenes such as styrene (1), 1,1-diphenylethene (2), and cis- and trans-stilbenes (3), but not triphenylethene (4), formed their contact charge-transfer (CCT) complexes with O2 in solutions. In zeolite NaY, the CCT absorption band was observed only for 1 and 3. Irradiation of alkenes 1–4 included in the zeolite nanocavities under O2 produced benzaldehyde and benzophenone as the major oxygenation products. In particular, for 3 and 4, the photooxygenation competed with a photoelectrocyclic reaction, which subsequently yielded phenanthrenes as the exclusive photoproducts under O2 in solution. It is likely that the oxygenation products were produced through the alkene cation radicals and superoxide anion radical generated by excitation of the CCT complexes and/or photoinduced electron transfer from the excited alkenes to O2. YAG laser (266 nm) excitation of 1 included in the zeolite cavities under vacuum produced its alkene cation radical and the trapped electron, Na43+, both of which were quenched by O2. On the basis of the optimum structure for the guest molecules obtained by semi-empirical molecular orbital calculations (AM1), it is suggested that the photooxygenation reaction was regulated by the electrostatic interaction between the guest molecules and alkali-metal cations in the nanocavities as well as by the strong electrostatic field which stabilized the ion radical pairs generated.

  苯乙烯（1）、1,1-二苯乙烯（2）、顺式和反式二苯乙烯（3）等芳香族烯烃（但不包括三苯乙烯（4））在溶液中与 O2 形成接触电荷转移（CCT）络合物。在沸石 NaY 中，只观察到 1 和 3 的 CCT 吸收带。在 O2 下辐照沸石纳米空腔中的烯 1-4 会产生苯甲醛和二苯甲酮作为主要的加氧产物。特别是对于 3 和 4，光氧合反应与光电环反应发生竞争，随后在溶液中的氧气条件下产生菲作为唯一的光产物。氧合产物很可能是通过 CCT 复合物激发产生的烯阳离子自由基和超氧阴离子自由基和/或激发的烯与 O2 之间的光诱导电子转移产生的。在真空条件下，YAG 激光（266 nm）激发沸石空腔中的 1 会产生烯阳离子自由基和捕获的电子 Na43+，这两种自由基都会被 O2 熄灭。根据半经验分子轨道计算（AM1）得到的客体分子最佳结构，可以认为光氧合反应是由纳米空腔中的客体分子和碱金属阳离子之间的静电相互作用以及稳定所产生的离子自由基对的强静电场调节的。
• 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.