9-(4-methoxyphenyl)-1H-phenalen-1-one | 65874-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9-(4-methoxyphenyl)-1H-phenalen-1-one
• 英文别名: 9-(4'-methoxyphenyl)-phenalen-1-one；9-(p-methoxyphenyl)-phenalen-1-one；9-(p-methoxyphenyl)perinaphthenone；9-(4-methoxyphenyl)phenalen-1-one；9-(4-Methoxyphenyl)phenalenon
• CAS: 65874-43-3
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: ZGRXGTCQXRGSEI-UHFFFAOYSA-N

物化性质

• 沸点：
  512.1±50.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-(4-methoxyphenyl)-1H-phenalen-1-one 在 叔丁基过氧化氢 、 苄基三甲基氢氧化铵 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 2,3-epoxi-9-(4-methoxyphenyl)phenalen-1-one
  参考文献：
  名称：

  Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

  摘要：

  Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

  DOI：

  10.1021/acs.jnatprod.7b00709
• 作为产物：
  描述：

  (E)-3-(naphthalen-1-yl)acrylic acid 在 aluminum (III) chloride 、 草酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.17h， 生成 9-(4-methoxyphenyl)-1H-phenalen-1-one
  参考文献：
  名称：

  Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer

  摘要：

  Concise total syntheses of the natural phytoalexins 2-hydroxy-8-(4-hydroxyphenyl)phenalen-1-one (1), 2-hydroxy-8-(3,4-dihydroxyphenyl)phenalen-1-one (2), and hydroxyanigorufone (4), together with regioisomer 3 are accomplished in 11 or 12 steps. The synthetic strategy features a Friedel Crafts acylation to construct the 1H-phenalen-1-one tricyclic core followed by a Suzuki cross-coupling to obtain the target compounds.

  DOI：

  10.1021/acs.jnatprod.7b00709

文献信息

• Synthesis and Antifungal Activity of Musa Phytoalexins and Structural Analogs
  作者：Winston Quiñones、Gustavo Escobar、Fernando Echeverri、Fernando Torres、Yoni Rosero、Victor Arango、Gloria Cardona、Adriana Gallego

  DOI：10.3390/50700974

  日期：——

  Winston Quinones, Gustavo Escobar, Fernando Echeverri *, Fernando Torres, Yoni Rosero,Vi ctor Arango, Gloria Cardona and Adriana GallegoDepartment of Chemistry, Universidad de Antioquia, P. O. Box 1226, Medellin, ColombiaTel.: (57+4)2105658, Fax: (57+4)2330120, E-mail: [e-mail] : 18 January 2000 ; revised form 14 July 2000 / Accepted : 14 July 2000 / Published : 26 July 2000Abstract:

  Winston Quinones、Gustavo Escobar、Fernando Echeverri *、Fernando Torres、Yoni Rosero、Victor Arango、Gloria Cardona 和 Adriana GallegoDepartment of Chemistry，Universidad de Antioquia，邮政信箱 1226，哥伦比亚麦德林电话：(57+4588105) (57+4)2330120，E-mail：[e-mail]收到：2000年1月18日；2000 年 7 月 14 日修订/接受：2000 年 7 月 14 日/出版：2000 年 7 月 26 日摘要：合成了几种环萘酮/苯萘酮化合物，以建立结构和对斐济分枝杆菌的抗真菌活性之间的关系。不饱和羰基系统上的取代或苯基的添加降低了抗生素活性。关键词
• Synthesis of[phenyl-13C6]lachnanthocarpone and other13C-labelled phenylphenalenones
  作者：Felipe Otálvaro、Winston Quiñones、Fernando Echeverri、Bernd Schneider

  DOI：10.1002/jlcr.808

  日期：2004.2

  [phenyl-13C6]Lachnanthocarpone ([phenyl-13C6]2,6-dihydroxy-9-phenylphenalen-1-one), a hypothetical intermediate in the biosynthesis of various natural phenylphenalenones, was prepared in four steps using [U-13C]bromobenzene to introduce the label. Based on related methodologies further native phenylphenalenones such as [phenyl-13C6]anigorufone, [1-13C]anigorufone and [4′-O13CH3]4′-methoxyanigorufone were synthesized in labelled form. Copyright © 2004 John Wiley & Sons, Ltd.

  [苯基-13C6]Lachnanthocarpone（[苯基-13C6]2,6-二羟基-9-苯基苯丙烯-1-酮）是多种天然苯丙烯酮生物合成过程中的假定中间体，利用[U-13C]溴苯引入标记，分四个步骤制备了该中间体。在相关方法的基础上，进一步合成了[苯基-13C6]苯并吡喃酮、[1-13C]苯并吡喃酮和[4′-O13CH3]4′-甲氧基苯并吡喃酮等标记形式的原生苯并芘。Copyright © 2004 John Wiley & Sons, Ltd. All Rights Reserved.
• Phenalenone-type phytoalexins from Musa acuminata synthesis of 4-phenyl-phenalenones
  作者：Javier G. Luis、Winston Q. Fletcher、Fernando Echeverri、Teresa A. Grillo

  DOI：10.1016/s0040-4020(01)85707-0

  日期：1994.1

  Two new 4-phenyl-phenalenone-type phytoalexins (2, 3) have been isolated from rhizomes of Musa acuminata infected with the fungus Fusarium oxysporum. The structures of the new phytoalexins were elucidated on the basis of spectroscopic evidence, chemical correlation and synthesis from commercial phenalen-1-one. The chemical shift for all of the hydrogen and carbon atoms in the substances were unambiguously established by mono- and bidimensional, homo- and heteronuclear NMR experiments (H-1 NMR, C-13 NMR COSY, HMQC and HMBC). In preliminary ''in vitro'' assays, the new phytoalexins have shown inhibitory activity on the growth of the germinative tube of Fusarium oxysporum f. sp. cubense race 4.
• Intermediates with biosynthetic implications in de novo production of phenyl-phenalenone-type phytoalexins by Musa acuminata revised structure of emenolone
  作者：Javier G. Luis、Winston Q. Fletcher、Fernando Echeverri、Teresa A. Grillo、Aurea Perales、JoséA. González

  DOI：10.1016/0040-4020(95)00129-v

  日期：1995.4

  Three new intermediates (1 - 3) in de novo biosynthetic pathway to phenyl-phenalenone-type phytoalexins have been isolated from rhizomes of Musa acuminata infected with the fungus Fusarium oxysporum. The structures of the new pre-phytoalexins were elucidated on the basis of spectroscopic evidences, chemical correlation and acid catalyzed biomimetic cyclization of 1 to emenolone (4), isolated from the same source and whose previously reported structure has been unambiguously corrected by X-ray diffraction analysis. The chemical shift for all of the hydrogen and carbon atoms in the substances were unambiguously established by mono- and bidimensional, homo- and heteronuclear NMR experiments (H-1 NMR, (1)3C NMR, COSY, ROESY, HMQC and HMBC).