2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran | 135040-88-9

• 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)-5-(3-acetoxypropyl)-7-methoxybenzofuran
• 英文别名: 5-(3-acetoxypropyl)-2-(4-hydroxy-3-methoxyphenyl)-7-methoxybenzofuran；3-[2-(4-Hydroxy-3-methoxyphenyl)-7-methoxy-1-benzofuran-5-yl]propyl acetate
• CAS: 135040-88-9
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: VBWFFHMMXGJLJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 potassium chloride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.5h， 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：

  3-(4-羟基-3-甲氧基苯基)-1-丙醇 在 palladium on activated charcoal 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 氢气 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxybenzofuran
  参考文献：
  名称：

  A new synthesis of the benzofuran adenosine antagonist XH-14

  摘要：

  5-(3-HydroxypropyI)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3-carbaldehyde (XH-14, 1) has been reported to be a potent A(1) adenosine antagonist. We have developed an efficient synthesis of this compound that should prove valuable for further structure-activity studies. The synthesis incorporates optimised methodology for the selective protection of a hydroxyl group and the ortho-bromination of a phenol. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10173-1

文献信息

• Total Synthesis of Ailanthoidol, Egonol, and Related Analogues
  作者：Xin-Fang Duan、Gang Shen、Zhan-Bin Zhang

  DOI：10.1055/s-0029-1219224

  日期：2010.4

  Efficient and general synthetic protocols were developed for the total synthesis of ailanthoidol, egonol, and some related analogues. The key transformations describe here involve a two-step construction of the benzofuran and a Sonogashira coupling, and proved to be convenient and effective, starting from readily available reagents. benzofurans - cross-coupling - McMurry reaction - ­Sonogashira coupling

  已开发出有效且通用的合成方案，用于全合成艾兰地洛尔，烯醇和一些相关类似物。这里描述的关键转化涉及苯并呋喃和Sonogashira偶联的两步构建，并且从容易获得的试剂开始证明是方便有效的。 苯并呋喃-交叉偶联-McMurry反应-Sonogashira偶联-天然产物
• Naturally occurring benzofuran: isolation, structure elucidation and total synthesis of 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde, a novel adenosine A1 receptor ligand isolated from salvia miltiorrhiza bunge (danshen)
  作者：Zhen Yang、Po Ming Hon、Kuk Ying Chui、Zun Le Xu、Hson Mou Chang、Chi Ming Lee、Yu Xin Cui、Henry N.C. Wong、Chi Duen Poon、Bing M. Fung

  DOI：10.1016/s0040-4039(00)78908-8

  日期：1991.4

  A naturally occurring benzofuran, namely 5-(3-hydroxypropyl)-7-methoxy-2-(3′-methoxy-4′-hydroxyphenyl)-3-benzo[b]furancarbaldehyde was isolated from the roots of S. miltiorrhiza Bunge “Danshen”. Its structure was established by means of spectroscopic methods as well as by a total synthesis. Both the natural and the synthetic compounds showed a high potency (IC50 = 17 nM and 10 nM, respectively) in

  从S. miltiorrhiza Bunge的根中分离出天然存在的苯并呋喃，即5-（3-羟丙基）-7-甲氧基-2-（3'-甲氧基-4'-羟基苯基）-3-苯并[ b ]呋喃甲醛。丹参”。它的结构是通过光谱方法以及通过全合成来确定的。天然化合物和合成化合物在牛腺苷A 1放射性配体结合中均显示出高效价（分别为IC 50 = 17 nM和10 nM）。
• Total Synthesis of Ailanthoidol and Precursor XH14 by Stille Coupling
  作者：Shun-Yu Lin、Chih-Lung Chen、Yean-Jang Lee

  DOI：10.1021/jo020653t

  日期：2003.4.1

  Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling reactions of benzofuranyl bromide with stannanyl compounds. This synthetic strategy can be modified to give access to a variety of different ailanthoidol and XH14 analogues.
• A new synthesis of the benzofuran adenosine antagonist XH-14
  作者：Sally A. Hutchinson、Henning Luetjens、Peter J. Scammells

  DOI：10.1016/s0960-894x(97)10173-1

  日期：1997.12

  5-(3-HydroxypropyI)-7-methoxy-2-(3'-methoxy-4'-hydroxyphenyl)benzo[b]furan-3-carbaldehyde (XH-14, 1) has been reported to be a potent A(1) adenosine antagonist. We have developed an efficient synthesis of this compound that should prove valuable for further structure-activity studies. The synthesis incorporates optimised methodology for the selective protection of a hydroxyl group and the ortho-bromination of a phenol. (C) 1997 Published by Elsevier Science Ltd.
• 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.