methyl 2-3-diethyl-1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylate | 1342899-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: methyl 2-3-diethyl-1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylate
• 英文别名: Methyl 2,3-diethyl-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylate；methyl 2,3-diethyl-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylate
• CAS: 1342899-44-8
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: DDLXLUAJZQEQBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-methoxycarbonyl-1,4-naphthoquinone 在 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 7.5h， 生成 methyl 2-3-diethyl-1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-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

文献信息

• Investigation towards an efficient synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones
  作者：Blaise Mavinga Mbala、Jan Jacobs、Pieter Claes、Virima Mudogo、Norbert De Kimpe

  DOI：10.1016/j.tet.2011.09.021

  日期：2011.11

  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.