3'-hydroxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one | 88126-45-8

• 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: 3'-hydroxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one
• 英文别名: 4-(3'-hydroxy-4'-methoxyphenyl)-5,7-dimethoxycoumarin；3'-hydroxy-4',5,7-trimethoxy-4-phenylcoumarin；3'-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin；5,7,4'-trimethoxy-3'-hydroxy-4-phenylcoumarin；4-(3-hydroxy-4-methoxyphenyl)-5,7-dimethoxychromen-2-one
• CAS: 88126-45-8
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: KOAAZLIOOBKJEK-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• 沸点：
  556.2±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-hydroxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one 在 4-二甲氨基吡啶 、 三甲基溴硅烷 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， -10.0~25.0 ℃ 、6.9 kPa 条件下， 反应 2.17h， 生成 disodium [2-methoxy-5-(5,7-methoxy-2-oxochromen-4-yl)phenyl]phosphate
  参考文献：
  名称：

  Synthesis of hydrophilic and lipophilic 4-arylcoumarin phosphates

  摘要：

  新型亲水性和疏水性前药，四芳基香豆烯二烷基磷酸盐和四芳基香豆烯二油酸磷酸盐，是通过将四芳基香豆烯与二烷基磷酸酯磷酸化合成的。

  DOI：

  10.1007/s11172-011-0304-7
• 作为产物：
  描述：

  异阿魏酸 在 sodium acetate 、 potassium carbonate 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 3'-hydroxy-4',5,7-trimethoxy-4-phenyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  细胞毒性 4-芳基香豆素的短合成

  摘要：

  摘要描述了在 CF3COOH 存在下，通过酚类与肉桂酸缩合，然后用 DDQ 脱氢，快速合成细胞毒性 4-芳基香豆素。

  DOI：

  10.1080/00397910500501235

文献信息

• 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.
• 4-Arylcoumarins from Coutarea hexandra
  作者：Giuliano Delle Monache、Bruno Botta、Amaro Serafim Neto、Roberto Alves De Lima

  DOI：10.1016/0031-9422(83)80104-6

  日期：1983.1
• Cytotoxic Constituents of the Roots of Exostema acuminatum
  作者：Aiko Ito、Hee-Byung Chai、Young Geun Shin、Ricardo Garcı́a、Miliciades Mejı́a、Qi Gao、Craig R Fairchild、Kate E Lane、Ana T Menendez、Norman R Farnsworth、Geoffrey A Cordell、John M Pezzuto、A Douglas Kinghorn

  DOI：10.1016/s0040-4020(00)00584-6

  日期：2000.8

  Bioassay-guided phytochemical investigation of the roots of Exostema acuminatum (Rubiaceae) using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of two norditerpenoids, namely, (16R)-ent-16,17-dihydroxy-19-nor-kaur-4-en-3-one (1) and (16S)-ent-16,17-dihydroxy-19-nor-kaur-4-en-3-one (2), and six previously known 4-phenylcoumarins (3-8). The structure and relative stereochemistry of the novel compound 1 were determined by X-ray crystallography. All isolates were tested against a panel of human tumor cell lines, and the 4-phenylcoumarins showed significant cytotoxicity, with 3'-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin (5) and 8-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin (6) exhibiting the most potent activity. Two of the 4-phenylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (3) and 6, were evaluated in an in vivo P388 murine leukemia model. (C) 2000 Elsevier Science Ltd. All rights reserved.