4'-hydroxy-5,7-dimethoxy-4-phenyl-2H-1-benzopyran-2-one | 88126-44-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4'-hydroxy-5,7-dimethoxy-4-phenyl-2H-1-benzopyran-2-one
• 英文别名: 5,7-dimethoxy-4-(4-hydroxyphenyl)-2H-1-benzopyran-2-one；4'-hydroxy-5,7-dimethoxy-4-phenylcoumarin；5,7-dimethoxy-4-(4-hydroxy-phenyl)-coumarin；4-(4-hydroxyphenyl)-5,7-dimethoxychromen-2-one
• CAS: 88126-44-7
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: ZCQHGWFKCJPSTB-UHFFFAOYSA-N

物化性质

• 熔点：
  204 °C
• 沸点：
  531.1±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  夫拉美诺 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 52.0h， 生成 4'-hydroxy-5,7-dimethoxy-4-phenyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Bose; Banerji, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 5, p. 422 - 424

  摘要：

  DOI：

文献信息

• Synthesis of 4-arylcoumarins from Coutarea hexandra
  作者：G Monache

  DOI：10.1016/s0031-9422(00)81132-2

  日期：——

  Abstract The structures assigned to the 5,7-dimethoxy-4-arylcoumarins isolated from Coutarea hexandra have been confirmed by synthesis, via Pechmann condensation of phloroglucinol and an ethyl benzoylacetate derivative, the hydroxy groups of which were protected either by benzylation or by methylenedioxy group formation.

  摘要 从 Coutarea hexandra 中分离出的 5,7-二甲氧基-4-芳基香豆素的结构已通过间苯三酚和苯甲酰乙酸乙酯衍生物的 Pechmann 缩合合成得到证实，其羟基被苄基化或亚甲二氧基保护。形成。
• Synthesis of New Naturally Occurring 4-Phenyl-2<i>H</i>-1-benzopyran-2-ones
  作者：Virinder S. Parmar、Rajni Jain、Suddham Singh

  DOI：10.1246/bcsj.61.2277

  日期：1988.6

  5,7-Dimethoxy-4-(4-hydroxyphenyl)-2H-1-benzopyran-2-one and 5,7-dimethoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-2-one, two new neoflavonoids occurring in Courtarea hexandra have been synthesized via Pechmann condensation. Attempts made to synthesize another 4-arylcoumarin, 5-hydroxy-7-methoxy-4-(2,5-dihydroxyphenyl)-2H-1-benzopyran-2-one, constituent of the same plant, led to the formation of the hitherto

  5,7-二甲氧基-4-(4-羟基苯基)-2H-1-苯并吡喃-2-one和5,7-二甲氧基-4-(4-甲氧基苯基)-2H-1-苯并吡喃-2-one，两个新的Courtarea hexandra 中的新黄酮类化合物是通过 Pechmann 缩合合成的。尝试合成另一种 4-芳基香豆素、5-羟基-7-甲氧基-4-(2,5-二羟基苯基)-2H-1-苯并吡喃-2-one，同一植物的成分，导致了迄今为止的形成未知 2-ethoxy-6-hydroxy-4H-1-benzopyran-4-one。
• Synthesis and antiprotozoal activity of 4-arylcoumarins
  作者：Jean-Thomas Pierson、Aurélien Dumètre、Sébastien Hutter、Florence Delmas、Michèle Laget、Jean-Pierre Finet、Nadine Azas、Sébastien Combes

  DOI：10.1016/j.ejmech.2009.10.022

  日期：2010.3

  synthesized by Suzuki-Miyaura cross-coupling reaction and evaluated for antiprotozoal activity against Plasmodium falciparum and Leishmania donovani. Several compounds were found to strongly inhibit the proliferation of human cell line and/or parasites. The 4-(3,4-dimethoxyphenyl)-6,7-dimethoxycoumarin exhibit a potent activity on L. donovani amastigotes with a selectivity index (SI = 265) twice than

  Suzuki-Miyaura交叉偶联反应合成了大量的4-芳基香豆素，并评估了其对恶性疟原虫和多形利什曼原虫的抗原生动物活性。发现几种化合物强烈抑制人细胞系和/或寄生虫的增殖。4-（3,4-二甲氧基苯基）-6,7-二甲氧基展览上的有效活性杜氏利什曼原虫的选择性指数（SI = 265）比两性霉素B（SI = 140）两次无鞭毛体。
• Synthesis of <i>C</i>-Ring Hydroxylated Neoflavonoids by Ligand Coupling Reactions
  作者：Dervilla M.X. Donnelly、Jean-Pierre Finet、Patrick J. Guiry、Martin D. Rea

  DOI：10.1080/00397919908086434

  日期：1999.8.1

  Reaction of 4-trifluoromethanesulfonyloxycoumarin derivatives with benzyloxyphenylboronic acid derivatives under modified Suzuki reaction conditions afforded the corresponding neoflavones. Selective debenzylation took place in high yields when the palladium-catalysed hydrogenolysis was performed in the presence of acetic acid.
• Synthesis of 4-Arylcoumarins via Cu-Catalyzed Hydroarylation with Arylboronic Acids
  作者：Yoshihiko Yamamoto、Naohiro Kirai

  DOI：10.1021/ol802239n

  日期：2008.12.18

  In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.