3-cyano-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran | 144735-76-2

• 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: 3-cyano-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
• 英文别名: 2-(4-Hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-1-benzofuran-3-carbonitrile
• CAS: 144735-76-2
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: BODTYIITKFXADB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-溴香兰素 在 palladium on activated charcoal 四氢吡咯 、 吡啶 、 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 potassium chloride 、 盐酸羟胺 、 氢气 、 sodium acetate 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 76.17h， 生成 3-cyano-5-(3-hydroxypropyl)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzofuran
  参考文献：
  名称：

  Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives

  摘要：

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.

  DOI：

  10.1021/jo00052a046

文献信息

• Compounds from Danshen. Part 7. Regioselective introduction of carbon-3 substituents to 5-alkyl-7-methoxy-2-phenylbenzo[b]furans: synthesis of a novel adenosine A1 receptor ligand and its derivatives
  作者：Zhen Yang、Han Biao Liu、Chi Ming Lee、Hson Mou Chang、Henry N. C. Wong

  DOI：10.1021/jo00052a046

  日期：1992.12

  By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.