4-(p-methoxyphenyl)-phenalen-1-one | 159853-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(p-methoxyphenyl)-phenalen-1-one
• 英文别名: 4-(4-methoxyphenyl)-1H-phenalen-1-one；4-(4-Methoxyphenyl)phenalen-1-one
• CAS: 159853-33-5
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: ZIMGGEXMXOMFEI-UHFFFAOYSA-N

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：

  4-(p-methoxyphenyl)-phenalen-1-one 在 叔丁基过氧化氢 、 苄基三甲基氢氧化铵 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  萘嵌苯酮 在 jones reagent 、 二异丁基氢化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 10.25h， 生成 4-(p-methoxyphenyl)-phenalen-1-one
  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

• Improved synthesis of 4-phenylphenalenones: the case of isoanigorufone and structural analogs
  作者：Marisol Cano、Carlos Rojas、William Hidalgo、Jairo Sáez、Jesús Gil、Bernd Schneider、Felipe Otálvaro

  DOI：10.1016/j.tetlet.2012.11.118

  日期：2013.1

  acid afforded the corresponding propionic acid which, after Friedel–Crafts acylation and bromine-mediated dehydrogenation, was subjected to Yang–Finnegan epoxidation to furnish 1. The preparation of analogs using this procedure is also discussed.

  从3-（2-羟基萘-1-基）丙腈开始，经九步合成2-羟基-4-苯基-1H-苯甲醛-1-酮（异苯丁二酮，1），是Mus草科专有的植物抗毒素。收率10％。从铃木-Miyaura的三氟甲磺酸酯和苯基硼酸之间的偶合得到的3-（2-苯基萘-1-基）丙酸乙酯的水解得到相应的丙酸，在Friedel-Crafts酰化和溴介导的脱氢后，将其进行Yang -芬尼根环氧化制得1。还讨论了使用该程序制备类似物。