3-[5-(Ethoxymethoxy)-7-methoxy-2-methyl-4-oxochromen-6-yl]propanal | 1446397-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-[5-(Ethoxymethoxy)-7-methoxy-2-methyl-4-oxochromen-6-yl]propanal
• 英文别名: 3-[5-(ethoxymethoxy)-7-methoxy-2-methyl-4-oxochromen-6-yl]propanal
• CAS: 1446397-69-8
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: HQSBMDKSQZHSNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[5-(Ethoxymethoxy)-7-methoxy-2-methyl-4-oxochromen-6-yl]propanal 在 三乙胺 、 (+)-二异松蒎基氯硼烷 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 9.67h， 生成 (7S)-7-(ethoxymethoxy)-1-[5-(ethoxymethoxy)-7-methoxy-2-methyl-4-oxochromen-6-yl]octane-3,5-dione
  参考文献：
  名称：

  Total Synthesis of Chaetoquadrins H and I

  摘要：

  The first total syntheses of the chromone-containing natural products chaetoquadrins H and I are reported, using an aldol reaction and an acid-catalyzed deprotection/cyclization/elimination sequence. Chaetoquadrin H was isolated from the ascomycete Chaetomium quadrangulatum and exhibits potent mouse liver monoamine oxidase (MAO) inhibitory activity. Chaetoquadrin I was not isolated in sufficient quantity to enable biological evaluation. The synthesis of the title compounds provides a useful starting point for a medicinal chemistry program focused on chaetoquadrin natural products.

  DOI：

  10.1055/s-0032-1318333
• 作为产物：
  描述：

  6-allyl-5-(ethoxymethoxy)-7-methoxy-2-methyl-4H-chromen-4-one 在 dimethyl sulfide borane 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 3-[5-(Ethoxymethoxy)-7-methoxy-2-methyl-4-oxochromen-6-yl]propanal
  参考文献：
  名称：

  Total Synthesis of Chaetoquadrins H and I

  摘要：

  The first total syntheses of the chromone-containing natural products chaetoquadrins H and I are reported, using an aldol reaction and an acid-catalyzed deprotection/cyclization/elimination sequence. Chaetoquadrin H was isolated from the ascomycete Chaetomium quadrangulatum and exhibits potent mouse liver monoamine oxidase (MAO) inhibitory activity. Chaetoquadrin I was not isolated in sufficient quantity to enable biological evaluation. The synthesis of the title compounds provides a useful starting point for a medicinal chemistry program focused on chaetoquadrin natural products.

  DOI：

  10.1055/s-0032-1318333

文献信息

• Total Synthesis of Chaetoquadrins H and I
  作者：Margaret Brimble、U Kim、Andrew Dalebrook、Daniel Furkert

  DOI：10.1055/s-0032-1318333

  日期：——

  The first total syntheses of the chromone-containing natural products chaetoquadrins H and I are reported, using an aldol reaction and an acid-catalyzed deprotection/cyclization/elimination sequence. Chaetoquadrin H was isolated from the ascomycete Chaetomium quadrangulatum and exhibits potent mouse liver monoamine oxidase (MAO) inhibitory activity. Chaetoquadrin I was not isolated in sufficient quantity to enable biological evaluation. The synthesis of the title compounds provides a useful starting point for a medicinal chemistry program focused on chaetoquadrin natural products.