2-(4-benzyloxy-2-methoxyphenyl)-6-methoxybenzofuran | 63604-96-6

• 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-benzyloxy-2-methoxyphenyl)-6-methoxybenzofuran
• 英文别名: 2-(4'-Benzyloxy-2-methoxyphenyl)-6-methoxybenzofuran；Vignafuran-benzylaether；6-Methoxy-2-(2-methoxy-4-phenylmethoxyphenyl)-1-benzofuran
• CAS: 63604-96-6
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: GMNDCHZZUFBYOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-benzyloxy-2-methoxyphenyl)-6-methoxybenzofuran 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 3-甲氧基-4-(6-甲氧基苯并呋喃-2-基)苯酚
  参考文献：
  名称：

  A Short-step Convenient Synthesis of 2-Phenylbenzofuran from 3-Phenylcoumarin

  摘要：

  The reaction mechanism of chemical conversion of (E)-beta-[2-hydroxylphenylcthylene]benzeneethanol into 2-phenylbenzofuran by DDQ, which involves loss of one carbon unit, was characterized and described. Five naturally occurring 2-phenylbenzofurans of not only the isoflavonoid but also stilbenoid origin were synthesized by use of this chemical scheme, which proved that this new scheme is a useful tool for quick synthesis of 2-phenylbenzofurans.

  DOI：

  10.3987/com-05-10424
• 作为产物：
  描述：

  2-Methyl-5-(tert-butyldimethylsilyloxy)phenyl N,N,N',N'-tetramethylphosphorodiamidate 在 甲酸 、 四甲基乙二胺 、 四丁基氟化铵 、 仲丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 9.5h， 生成 2-(4-benzyloxy-2-methoxyphenyl)-6-methoxybenzofuran
  参考文献：
  名称：

  A short and convergent synthesis of the phytoalexins vignafuran, 6-demethylvignafuran, and moracin M via directed lithiation reaction.

  摘要：

  2-甲基-5-(叔丁基二甲基硅氧基)苯基 N, N, N', N'-四甲基磷酸二胺盐与 sec-BuLi 在 N, N, N', N'-四甲基乙烯二胺的存在下，在 -105°C 下进行锂化，生成相应的苄阴离子。该苄阴离子与各种甲基苯甲酸酯反应，生成去氧苯醌衍生物，这些衍生物在未进行纯化的情况下与甲酸处理，得到 2-芳基-6-羟基苯并[b]呋喃。该策略的实用性已通过其在短时间合成植物抗生素中的应用得以验证，如 viganfuran、6-去甲基 viganfuran 和 moracin M。

  DOI：

  10.1248/cpb.39.579

文献信息

• A Short-step Convenient Synthesis of 2-Phenylbenzofuran from 3-Phenylcoumarin
  作者：Takeshi Kinoshita、Koji Ichinose

  DOI：10.3987/com-05-10424

  日期：——

  The reaction mechanism of chemical conversion of (E)-beta-[2-hydroxylphenylcthylene]benzeneethanol into 2-phenylbenzofuran by DDQ, which involves loss of one carbon unit, was characterized and described. Five naturally occurring 2-phenylbenzofurans of not only the isoflavonoid but also stilbenoid origin were synthesized by use of this chemical scheme, which proved that this new scheme is a useful tool for quick synthesis of 2-phenylbenzofurans.
• A short and convergent synthesis of the phytoalexins vignafuran, 6-demethylvignafuran, and moracin M via directed lithiation reaction.
  作者：Mitsuaki WATANABE、Kenji KAWANISHI、Sunao FURUKAWA

  DOI：10.1248/cpb.39.579

  日期：——

  2-Methyl-5-(tert-butyldimethylsilyloxy)phenyl N, N, N', N'-tetramethylphosphorodiamidate was lithiated with sec-BuLi in the presence of N, N, N', N'-tetramethylethylenediamine at -105°C to generate the corresponding benzylic anion. This benzylic anion was reacted with various methyl benzoates to provide deoxybenzoin derivatives which, without purification, were treated with formic acid to give 2-aryl-6-hydroxybenzo[b]furans. The utility of this strategy has been demonstrated by its application to the short synthesis of phytoalexins, such as vignafuran, 6-demethylvignafuran, and moracin M.

  2-甲基-5-(叔丁基二甲基硅氧基)苯基 N, N, N', N'-四甲基磷酸二胺盐与 sec-BuLi 在 N, N, N', N'-四甲基乙烯二胺的存在下，在 -105°C 下进行锂化，生成相应的苄阴离子。该苄阴离子与各种甲基苯甲酸酯反应，生成去氧苯醌衍生物，这些衍生物在未进行纯化的情况下与甲酸处理，得到 2-芳基-6-羟基苯并[b]呋喃。该策略的实用性已通过其在短时间合成植物抗生素中的应用得以验证，如 viganfuran、6-去甲基 viganfuran 和 moracin M。