methyl 5-(2-hydroxyacetyl)-6-(ethoxymethoxy)-4-(methoxycarbonyl)methoxyquinoline-2-carboxylate | 1560725-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 5-(2-hydroxyacetyl)-6-(ethoxymethoxy)-4-(methoxycarbonyl)methoxyquinoline-2-carboxylate
• CAS: 1560725-16-7
• 化学式: C₁₉H₂₁NO₉
• 分子量: 407.377
• InChiKey: AJTRWYZMBSKUNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  61-63 °C
• 沸点：
  567.6±50.0 °C(predicted)
• 密度：
  1.324±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  130.48
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl 5-(2-hydroxyacetyl)-6-(ethoxymethoxy)-4-(methoxycarbonyl)methoxyquinoline-2-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 6.0h， 以48%的产率得到methyl 1-(ethoxymethoxy)-8-oxo-8,10-dihydrofuro[3',4':5,6]pyrano[2,3,4-de]quinoline-5-carboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-Distomadines A and B

  摘要：

  The total synthesis of distomadines A and B, two structurally unique tetracyclic quinolines, is described. The route features a three-step process to access the pyranoquinoline butenolide rings via a Suzuki cross coupling of a 5-bromo-4-methoxycarbonylmethoxyquinoline with a vinyl boronate, followed by an alpha-ketohydroxylation and double cyclization by intramolecular aldol condensation and lactonization. Subsequent manipulation of the side chain to introduce the guanidine fragment completed the synthesis of distomadine B, whereas the distomadine A congener resulted from decarboxylation of a late-stage intermediate.

  DOI：

  10.1021/ol403598k
• 作为产物：
  描述：

  methyl 5-bromo-6-ethoxymethoxy-4-(methoxycarbonyl)methoxyquinoline-2-carboxylate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium permanganate 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 丙酮 为溶剂， 反应 18.33h， 生成 methyl 5-(2-hydroxyacetyl)-6-(ethoxymethoxy)-4-(methoxycarbonyl)methoxyquinoline-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of (±)-Distomadines A and B

  摘要：

  The total synthesis of distomadines A and B, two structurally unique tetracyclic quinolines, is described. The route features a three-step process to access the pyranoquinoline butenolide rings via a Suzuki cross coupling of a 5-bromo-4-methoxycarbonylmethoxyquinoline with a vinyl boronate, followed by an alpha-ketohydroxylation and double cyclization by intramolecular aldol condensation and lactonization. Subsequent manipulation of the side chain to introduce the guanidine fragment completed the synthesis of distomadine B, whereas the distomadine A congener resulted from decarboxylation of a late-stage intermediate.

  DOI：

  10.1021/ol403598k