methyl 3-acetyl-2,3-dihydro-5-hydroxy-2-oxonaphtho[1,2-b]furan-4-carboxylate | 1342899-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: methyl 3-acetyl-2,3-dihydro-5-hydroxy-2-oxonaphtho[1,2-b]furan-4-carboxylate
• CAS: 1342899-32-4
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: XUIXTSXSNJHVLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  89.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 3-acetyl-2,3-dihydro-5-hydroxy-2-oxonaphtho[1,2-b]furan-4-carboxylate 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以67%的产率得到methyl 2,3-dihydro-5-hydroxy-2-oxonaphtho[1,2-b]furan-4-carboxylate
  参考文献：
  名称：

  Investigation towards an efficient synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones

  摘要：

  As part of our research on 2-aza analogues of pentalongin, the active principle of Pentas longiflora Oliv., the first synthesis of 2,3-disubstituted benzo[g]isoquinoline-1,5,10(2H)-triones via 3,4-disubstituted 6-hydroxybenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-diones as the key intermediates is reported. The latter compounds have been prepared by treating 2-methoxycarbonyl-1,4-naphthoquinone with N-substituted enaminoesters under acidic conditions. These reagents are easily accessible from readily available 1,4-dihydroxy-2-naphthoic acid, beta-ketoesters and primary amines. Finally, a short synthesis of substituted benzo[g]isoquinoline-1,5,10(2H)-triones is achieved by an oxidative addition of N-substituted enaminoesters onto methyl 1,4-dihydroxynaphthalene-2-carboxylate. (C) 2011 Elsevier Ad. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.021
• 作为产物：
  描述：

  2-methoxycarbonyl-1,4-naphthoquinone 、 乙酰乙酸乙酯 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以54%的产率得到methyl 3-acetyl-2,3-dihydro-5-hydroxy-2-oxonaphtho[1,2-b]furan-4-carboxylate
  参考文献：
  名称：

  Investigation towards an efficient synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones

  摘要：

  As part of our research on 2-aza analogues of pentalongin, the active principle of Pentas longiflora Oliv., the first synthesis of 2,3-disubstituted benzo[g]isoquinoline-1,5,10(2H)-triones via 3,4-disubstituted 6-hydroxybenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-diones as the key intermediates is reported. The latter compounds have been prepared by treating 2-methoxycarbonyl-1,4-naphthoquinone with N-substituted enaminoesters under acidic conditions. These reagents are easily accessible from readily available 1,4-dihydroxy-2-naphthoic acid, beta-ketoesters and primary amines. Finally, a short synthesis of substituted benzo[g]isoquinoline-1,5,10(2H)-triones is achieved by an oxidative addition of N-substituted enaminoesters onto methyl 1,4-dihydroxynaphthalene-2-carboxylate. (C) 2011 Elsevier Ad. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.021