5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)benzofuran | 144735-58-0

• 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: 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)benzofuran
• 英文别名: 3-[2-(4-Acetyloxy-3-methoxyphenyl)-7-methoxy-1-benzofuran-5-yl]propyl acetate
• CAS: 144735-58-0
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: BTNSSFUAJOZTAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)benzofuran 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 sodium hydroxide 、 potassium chloride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 17.17h， 生成 5-(3-hydroxypropyl)-7-methoxy-3-methyl-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
• 作为产物：
  描述：

  1-(苄氧基)-4-乙炔基-2-甲氧基苯 在 palladium on activated charcoal 吡啶 、 ammonium hydroxide 、 lithium aluminium tetrahydride 、 盐酸羟胺 、 氢气 、 copper(II) sulfate 作用下， 以 四氢呋喃 为溶剂， 反应 52.0h， 生成 5-(3-acetoxypropyl)-7-methoxy-2-(3'-methoxy-4'-acetoxyphenyl)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