2-羟基-4-(4-羟基苯基)-1H-萘嵌苯-1-酮 | 149184-19-0

• 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-羟基苯基)-1H-萘嵌苯-1-酮
• 英文名称: irenolone
• 英文别名: 2-hydroxy-4-(4-hydroxyphenyl)phenalen-1-one
• CAS: 149184-19-0
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: UQMKPTIDKHEGFW-UHFFFAOYSA-N

物化性质

• 沸点：
  573.7±50.0 °C(Predicted)
• 密度：
  1.433±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  285°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-4-(4-羟基苯基)-1H-萘嵌苯-1-酮 以 甲醇 、 乙醚 为溶剂， 反应 0.02h， 生成 2-methoxy-4-(4-methoxyphenyl)-1H-phenalen-1-one
  参考文献：
  名称：

  Phenylphenalenone-type Phytoalexins from Unripe Buñgulan Banana Fruit

  摘要：

  从未熟的麝香草 [AAA] cv. Buñgulan 果实的果皮中分离出 14 种苯丙芘酮类植物毒素（1-14），其中包括三种新化合物。Buñgulan 果实受伤后接种了 Colletotrichum musae 的分生孢子。这些新的植物毒素被鉴定为 (+)-cis-2,3-dihydro-2,3-dihydroxy-4-(4′-hydroxyphenyl)phenalen-1-one (12)、9-(3′,4′-dimethoxyphenyl)-2-methoxyphenalen-1-one (13) 和 9-(4′-hydroxyphenyl)-2-methoxyphenalen-1-one (14)。利用电离质谱中[M]+/[M-H]+离子或[M-H2O]+/[M-H2O-H]+离子的相对强度比来区分 4-苯基和 9-苯基苯丙烯酮。对植物醛毒素进行的抗真菌测试表明，酚羟基对其活性至关重要。

  DOI：

  10.1271/bbb.62.95
• 作为产物：
  描述：

  萘嵌苯酮 在 叔丁基过氧化氢 、 jones reagent 、 三溴化硼 、 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 12.5h， 生成 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

文献信息

• Phenylphenalenone-type Phytoalexins from Unripe Buñgulan Banana Fruit
  作者：Tsunashi KAMO、Nagomi KATO、Nobuhiro HIRAI、Mitsuya TSUDA、Daie FUJIOKA、Hajime OHIGASHI

  DOI：10.1271/bbb.62.95

  日期：1998.1

  Fourteen phenylphenalenone-type phytoalexins (1-14), including three new compounds, were isolated from the peel of unripe Musa acuminata [AAA] cv. Buñgulan fruit which had been injured and then inoculated with conidia of Colletotrichum musae. These new phytoalexins were identified as (+)-cis-2,3-dihydro-2,3-dihydroxy-4-(4′-hydroxyphenyl)phenalen-1-one (12), 9-(3′,4′-dimethoxyphenyl)-2-methoxyphenalen-1-one (13) and 9-(4′-hydroxyphenyl)-2-methoxyphenalen-1-one (14). The ratios of the relative intensities of the [M]+/[M-H]+ ions or [M-H2O]+/[M-H2O-H]+ ions in the EI mass spectra were applied to discriminate between 4- and 9-phenylphenalenones. An antifungal test on the phytoalexins showed that a phenolic hydroxyl group was essential for the activity.

  从未熟的麝香草 [AAA] cv. Buñgulan 果实的果皮中分离出 14 种苯丙芘酮类植物毒素（1-14），其中包括三种新化合物。Buñgulan 果实受伤后接种了 Colletotrichum musae 的分生孢子。这些新的植物毒素被鉴定为 (+)-cis-2,3-dihydro-2,3-dihydroxy-4-(4′-hydroxyphenyl)phenalen-1-one (12)、9-(3′,4′-dimethoxyphenyl)-2-methoxyphenalen-1-one (13) 和 9-(4′-hydroxyphenyl)-2-methoxyphenalen-1-one (14)。利用电离质谱中[M]+/[M-H]+离子或[M-H2O]+/[M-H2O-H]+离子的相对强度比来区分 4-苯基和 9-苯基苯丙烯酮。对植物醛毒素进行的抗真菌测试表明，酚羟基对其活性至关重要。
• 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.