2-hydroxy-9-(4-methoxyphenyl)-1H-phenalen-1-one | 65874-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-9-(4-methoxyphenyl)-1H-phenalen-1-one
• 英文别名: 2-Hydroxy-9-(4-methoxyphenyl)phenalen-1-one
• CAS: 65874-44-4
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: IDDOHJSCLCKCAC-UHFFFAOYSA-N

物化性质

• 沸点：
  564.3±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-9-(4-methoxyphenyl)-1H-phenalen-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到2-羟基-9-(4-羟基苯基)-1H-萘嵌苯-1-酮
  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 叔丁基过氧化氢 、 aluminum (III) chloride 、 草酰氯 、 苄基三甲基氢氧化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 7.17h， 生成 2-hydroxy-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

• 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).
• Concise Synthesis of Natural Phenylphenalenone Phytoalexins and a Regioisomer
  作者：Ming-Zhong Wang、Chuen-Fai Ku、Tong-Xu Si、Siu-Wai Tsang、Xiao-Meng Lv、Xiao-Wan Li、Zheng-Ming Li、Hong-Jie Zhang、Albert S. C. Chan

  DOI：10.1021/acs.jnatprod.7b00709

  日期：2018.1.26

  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.