4-ethyl-6-hydroxy-3-methylbenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-dione | 1342899-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 4-ethyl-6-hydroxy-3-methylbenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-dione
• 英文别名: 11-ethyl-8-hydroxy-12-methyl-15-oxa-11-azatetracyclo[7.6.1.02,7.013,16]hexadeca-1(16),2,4,6,8,12-hexaene-10,14-dione
• CAS: 1342899-39-1
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: NDIBKNMAGDVMFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-ethyl-6-hydroxy-3-methylbenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-dione 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.5h， 生成 2-ethyl-3-methyl-1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylic acid
  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 、 ethyl 3-ethylamino-2-butenoate 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以33%的产率得到4-ethyl-6-hydroxy-3-methylbenzo[g]furo[4,3,2-de]isoquinoline-2,5(4H)-dione
  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.