2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-propylbenzofuran | 215585-96-9

• 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-hydroxy-3-methoxyphenyl)-7-methoxy-5-propylbenzofuran
• 英文别名: 2-Methoxy-4-(7-methoxy-5-propyl-1-benzofuran-2-yl)phenol；2-methoxy-4-(7-methoxy-5-propyl-1-benzofuran-2-yl)phenol
• CAS: 215585-96-9
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: ZEYXFDYYKADEGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰化锌 、 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-propylbenzofuran 在 盐酸 、 potassium chloride 作用下， 生成 2-(4'-hydroxy-3'-methoxyphenyl)-7-methoxy-5-propylbenzo[b]furan-3-carbaldehyde
  参考文献：
  名称：

  XH-14 analogues as adenosine antagonists

  摘要：

  Analogues of the potent adenosine antagonist 5-(3'-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3-carbaldehyde (XH-14, 1) with alternate substituents in the 2-, 5- and 7-positions have been synthesised. The affinity of these compounds for the Al adenosine receptor has been evaluated using a [H-3]CPX competitive binding assay. This structure-activity study highlighted the importance of the 3-formyl and 5-(3-hydroxypropyl) moieties for high receptor affinity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00093-5
• 作为产物：
  描述：

  4-丙基苯酚 在 palladium on activated charcoal 氢气 、 溴 、 溶剂黄146 、 copper dichloride 、 barium(II) oxide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-propylbenzofuran
  参考文献：
  名称：

  XH-14 analogues as adenosine antagonists

  摘要：

  Analogues of the potent adenosine antagonist 5-(3'-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3-carbaldehyde (XH-14, 1) with alternate substituents in the 2-, 5- and 7-positions have been synthesised. The affinity of these compounds for the Al adenosine receptor has been evaluated using a [H-3]CPX competitive binding assay. This structure-activity study highlighted the importance of the 3-formyl and 5-(3-hydroxypropyl) moieties for high receptor affinity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00093-5

文献信息

• A Concise Synthesis of Natural Benzofuran Neolignans and Analogues
  作者：Xin-Fang Duan、Gang Shen、Zhan-Bin Zhang

  DOI：10.1055/s-0029-1218826

  日期：2010.8

  of four naturally occurring benzofuran neolignans and two analogues was achieved in four steps in 44-51% overall yield. Key steps involved a two-step construction of benzofuran nucleus and a Suzuki coupling. This synthesis has been proven straightforward and efficient, and more related analogues can be prepared for structure-activity relationship explorations. benzofuran - neolignan - McMurry reaction

  四个天然的苯并呋喃新木脂素和两个类似物的第一次总合成分四个步骤完成，总产率为44-51％。关键步骤涉及苯并呋喃核和Suzuki偶联的两步构建。该合成已被证明是直接有效的，并且可以制备更多相关的类似物用于结构-活性关系探索。 苯并呋喃-Neolignan-McMurry反应-Suzuki偶联
• XH-14 analogues as adenosine antagonists
  作者：Peter J. Scammells、Stephen P. Baker、Anthony R. Beauglehole

  DOI：10.1016/s0968-0896(98)00093-5

  日期：1998.9

  Analogues of the potent adenosine antagonist 5-(3'-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3-carbaldehyde (XH-14, 1) with alternate substituents in the 2-, 5- and 7-positions have been synthesised. The affinity of these compounds for the Al adenosine receptor has been evaluated using a [H-3]CPX competitive binding assay. This structure-activity study highlighted the importance of the 3-formyl and 5-(3-hydroxypropyl) moieties for high receptor affinity. (C) 1998 Elsevier Science Ltd. All rights reserved.