2-[4,6-dihydroxy-3-(γ,γ-dimethylallyl)-2-methoxyphenyl]-6-hydroxy-3-methyl-benzofuran | 1253641-15-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-[4,6-dihydroxy-3-(γ,γ-dimethylallyl)-2-methoxyphenyl]-6-hydroxy-3-methyl-benzofuran
• 英文别名: glycybenzofuran；4-(6-hydroxy-3-methyl-1-benzofuran-2-yl)-5-methoxy-6-(3-methylbut-2-enyl)benzene-1,3-diol
• CAS: 1253641-15-4
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: OEIIVGQLDAYZNT-UHFFFAOYSA-N

物化性质

• 沸点：
  399.0±37.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  83.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4,6-dihydroxy-3-(γ,γ-dimethylallyl)-2-methoxyphenyl]-6-hydroxy-3-methyl-benzofuran 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 24.0h， 以81%的产率得到6-methoxy-3-methyl-2-(2,4,6-trimethoxy-3-(3-methylbut-2-en-1-yl)phenyl)benzofuran
  参考文献：
  名称：

  Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities

  摘要：

  Two new 2-arylbenzofurans, glycybenzofuran (1) and cyclolicocoumarone (2), together with 10 known flavonoids including licocoumarone (3), glycyrrhisoflavone (4), glisoflavone (5), cycloglycyrrhisoflavone (6), isoliquiritigenin (7), licoflavone A (8), apigenin (9), isokaempferide (10), glycycoumarin (11), and isoglycycoumarin (12), were isolated from the roots of Glycyrrhiza uralensis and their structures were determined by extensive spectroscopic analyses. Compounds 1 and 5 showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity in vitro with the IC50 values of 25.5 and 27.9 mu M, respectively. The structure-activity relationship indicated that the presence of prenyl group and ortho-hydroxy group is important for exhibiting the activity. Kinetic analysis indicated that compound 1 inhibits PTP1B by a competitive mode, whereas compound 5 by a mixed mode. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.110
• 作为产物：
  描述：

  6-(benzyloxy)-3-((3,5-bis(benzyloxy)phenoxy)methyl)benzofuran 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 palladium 10% on activated carbon 、 camphor sulfonic acid 、 氢气 、 silica gel 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 102.5h， 生成 2-[4,6-dihydroxy-3-(γ,γ-dimethylallyl)-2-methoxyphenyl]-6-hydroxy-3-methyl-benzofuran
  参考文献：
  名称：

  通过级联[3,3]-σ重排/芳构化策略集体合成2-（3-甲基苯并呋喃-2-基）苯酚衍生的天然产物

  摘要：

  开发了一种级联[3,3]-σ重排/芳构化策略来合成2-（3-甲基苯并呋喃-2-基）苯酚衍生物，并将其应用于集体合成七个含2-芳基苯并呋喃的天然产物，即糖基苯并呋喃，甘油尿嘧啶E，来昔多酚A 1，葛根呋喃，7,2'，4'-三羟基-3-苯并呋喃羧酸，香豆酚和4'- O-甲基香豆酚。其中，糖基苯并呋喃，糖尿素E，葛根素，7,2'，4'-三羟基-3-苯并呋喃羧酸和4'- O的总合成-甲基香豆酚是首次报道。通过以克规模进行反应并通过在常见策略中用2-（3-甲基苯并呋喃-2-基）苯酚支架合成一系列天然产物，证明了该新颖策略在制备关键中间体中的实用性。

  DOI：

  10.1021/acs.joc.7b02066

文献信息

• Collective Syntheses of 2-(3-Methylbenzofuran-2-yl)phenol-Derived Natural Products by a Cascade [3,3]-Sigmatropic Rearrangement/Aromatization Strategy
  作者：Yingzhan Tang、Chongguo Jiang、Xinhang Zhang、Chengjun Liu、Jingsheng Lin、Yanshi Wang、Chuan Du、Xiaoshi Peng、Wei Li、Yongxiang Liu、Maosheng Cheng

  DOI：10.1021/acs.joc.7b02066

  日期：2017.10.20

  strategy to the synthesis of 2-(3-methylbenzofuran-2-yl)phenol derivatives was developed and applied to the collective syntheses of seven 2-arylbenzofuran-containing natural products, namely glycybenzofuran, glycyuralin E, lespedezol A1, puerariafuran, 7,2′,4′-trihydroxy-3-benzofurancarboxylic acid, coumestrol, and 4′-O-methylcoumestrol. Among them, the total syntheses of glycybenzofuran, glycyuralin

  开发了一种级联[3,3]-σ重排/芳构化策略来合成2-（3-甲基苯并呋喃-2-基）苯酚衍生物，并将其应用于集体合成七个含2-芳基苯并呋喃的天然产物，即糖基苯并呋喃，甘油尿嘧啶E，来昔多酚A 1，葛根呋喃，7,2'，4'-三羟基-3-苯并呋喃羧酸，香豆酚和4'- O-甲基香豆酚。其中，糖基苯并呋喃，糖尿素E，葛根素，7,2'，4'-三羟基-3-苯并呋喃羧酸和4'- O的总合成-甲基香豆酚是首次报道。通过以克规模进行反应并通过在常见策略中用2-（3-甲基苯并呋喃-2-基）苯酚支架合成一系列天然产物，证明了该新颖策略在制备关键中间体中的实用性。
• Prenylflavonoids from Glycyrrhiza uralensis and their protein tyrosine phosphatase-1B inhibitory activities
  作者：Songpei Li、Wei Li、Yinghua Wang、Yoshihisa Asada、Kazuo Koike

  DOI：10.1016/j.bmcl.2010.07.110

  日期：2010.9

  Two new 2-arylbenzofurans, glycybenzofuran (1) and cyclolicocoumarone (2), together with 10 known flavonoids including licocoumarone (3), glycyrrhisoflavone (4), glisoflavone (5), cycloglycyrrhisoflavone (6), isoliquiritigenin (7), licoflavone A (8), apigenin (9), isokaempferide (10), glycycoumarin (11), and isoglycycoumarin (12), were isolated from the roots of Glycyrrhiza uralensis and their structures were determined by extensive spectroscopic analyses. Compounds 1 and 5 showed significant protein tyrosine phosphatase-1B (PTP1B) inhibitory activity in vitro with the IC50 values of 25.5 and 27.9 mu M, respectively. The structure-activity relationship indicated that the presence of prenyl group and ortho-hydroxy group is important for exhibiting the activity. Kinetic analysis indicated that compound 1 inhibits PTP1B by a competitive mode, whereas compound 5 by a mixed mode. (c) 2010 Elsevier Ltd. All rights reserved.