2-hydroxy-4-methoxy-9-phenyl-1H-phenalene-1-one | 1245705-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-4-methoxy-9-phenyl-1H-phenalene-1-one
• 英文别名: 2-hydroxy-4-methoxy-9-phenyl-1H-phenalen-1-one；2-Hydroxy-4-methoxy-9-phenylphenalen-1-one
• CAS: 1245705-64-9
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: QKRDXFNAWQRAKY-UHFFFAOYSA-N

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-4-methoxy-9-phenyl-1H-phenalene-1-one 在 水 、 氢溴酸 、 溶剂黄146 作用下， 反应 6.0h， 以84%的产率得到2,4-dihydroxy-9-phenyl-1H-phenalen-1-one
  参考文献：
  名称：

  Synthesis of musafluorone: a naphthoxanthenone isolated from Musa acuminata

  摘要：

  5-Methoxy-3H-naphtho[2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium bromide to 4-methoxyperinaphthenone afforded the corresponding 4-methoxy-9-phenylphenalenone which, after epoxidation and methyl transposition, was subjected to a photochemical cyclization procedure to furnish 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.128
• 作为产物：
  描述：

  4-methoxy-9-phenyl-1H-phenalen-1-one 在 4-苯基吡啶-N-氧化物 、 calcium chlorite 、 (S,S)-(+)-[N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-diaminocyclohexane]manganese(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以50%的产率得到2-hydroxy-4-methoxy-9-phenyl-1H-phenalene-1-one
  参考文献：
  名称：

  Synthesis of musafluorone: a naphthoxanthenone isolated from Musa acuminata

  摘要：

  5-Methoxy-3H-naphtho[2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium bromide to 4-methoxyperinaphthenone afforded the corresponding 4-methoxy-9-phenylphenalenone which, after epoxidation and methyl transposition, was subjected to a photochemical cyclization procedure to furnish 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.128

文献信息

• Synthesis of musafluorone: a naphthoxanthenone isolated from Musa acuminata
  作者：Luisa Duque、Catalina Restrepo、Jairo Sáez、Jesús Gil、Bernd Schneider、Felipe Otálvaro

  DOI：10.1016/j.tetlet.2010.06.128

  日期：2010.9

  5-Methoxy-3H-naphtho[2,1,8-mna]xanthen-3-one (musafluorone, 1), the only naphthoxanthenone reported so far from Musaceae, was synthesized starting from 2-naphthol in nine steps and resulted in an overall yield of 3%. Grignard addition of phenylmagnesium bromide to 4-methoxyperinaphthenone afforded the corresponding 4-methoxy-9-phenylphenalenone which, after epoxidation and methyl transposition, was subjected to a photochemical cyclization procedure to furnish 1. (C) 2010 Elsevier Ltd. All rights reserved.
• Radical Scavenging Capacity of 2,4-Dihydroxy-9-phenyl-1<i>H</i>-phenalen-1-one: A Functional Group Exclusion Approach
  作者：Luisa Duque、Carolina Zapata、Benjamín Rojano、Bernd Schneider、Felipe Otálvaro

  DOI：10.1021/ol400384z

  日期：2013.7.19

  2,4-Dihydroxy-9-phenyl-1H-phenalen-1-one (4-hydroxyanigorufone, 1), a compound isolated from Anigozanthos flavidus and Monochoria elate, displayed a high radical scavenging capacity in the ORAC assay. A systematic approach was adopted in order to explore the effect of each functional group. H-Atom transfer from the phenolic hydroxyl, a captodative effect from the hydroxy ketone, and the presumed involvement of the phenyl ring in the termination step of the radical reaction were disclosed as relevant features of this type of antioxidant