2-羟基-4-(4-甲氧基苯基)-1H-萘嵌苯-1-酮 | 159853-36-8

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-羟基-4-(4-甲氧基苯基)-1H-萘嵌苯-1-酮
• 英文名称: 2-hydroxy-4-(4'-methoxyphenyl)phenalen-1-one
• 英文别名: 4'-methoxyirenolone；2-hydroxy-4-(4-methoxyphenyl)-1H-phenalen-1-one；2-hydroxy-4-(4-methoxyphenyl)phenalen-1-one
• CAS: 159853-36-8
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: PVZKBQMWQRUUFI-UHFFFAOYSA-N

物化性质

• 沸点：
  555.8±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  222-223°C

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-羟基-4-(4-甲氧基苯基)-1H-萘嵌苯-1-酮 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到2-羟基-4-(4-羟基苯基)-1H-萘嵌苯-1-酮
  参考文献：
  名称：

  Phenalenone-type phytoalexins from Musa acuminata synthesis of 4-phenyl-phenalenones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)85707-0
• 作为产物：
  描述：

  萘嵌苯酮 在 叔丁基过氧化氢 、 jones reagent 、 苄基三甲基氢氧化铵 、 二异丁基氢化铝 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 12.25h， 生成 2-羟基-4-(4-甲氧基苯基)-1H-萘嵌苯-1-酮
  参考文献：
  名称：

  Phenalenone-type phytoalexins from Musa acuminata synthesis of 4-phenyl-phenalenones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)85707-0

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).

表征谱图