3-amino-2-methoxycarbonyl-1,4-naphthoquinone | 99336-62-6

• 物质功能分类: 化学试剂 - 有机试剂 - 肼
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-amino-2-methoxycarbonyl-1,4-naphthoquinone
• 英文别名: 2-amino-3-carbomethoxy-1,4-naphthoquinone；methyl 3-amino-1,4-dioxonaphthalene-2-carboxylate
• CAS: 99336-62-6
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: IXTNIIRZNKCDBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-amino-2-methoxycarbonyl-1,4-naphthoquinone 在 lead(IV) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以79%的产率得到3-methoxynaphth<2,3-c>isoxazole-4,9-quinone
  参考文献：
  名称：

  Torres, Tomas; Eswaran, S.V.; Schaefer, Wolfram, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 697 - 699

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methoxycarbonyl-1,4-naphthoquinone 在 air 、 ammonium acetate 、 溶剂黄146 作用下， 反应 4.0h， 以83%的产率得到3-amino-2-methoxycarbonyl-1,4-naphthoquinone
  参考文献：
  名称：

  New and highly efficient synthesis of 3-substituted 1-hydroxybenz[g]isoquinoline-5,10-diones

  摘要：

  A new and efficient strategy for the synthesis of 3-substituted 1-hydroxybenz[g]isoquinoline-5,10-diones by reaction of 2-methoxycarbonyl-1,4-naphthoquinone with different pyridinium salts under Krohnke conditions is disclosed, This one-step reaction Was found to be dependent on the substitution pattern of the aromatic nucleus in the pyridinium salts. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.070

文献信息

• A New Convenient Synthesis of Phosphoranylideneaminoquinones from Isoxazolequinones
  作者：Salomé Rodríguez-Morgade、Tomás Torres、Purificación Vázquez

  DOI：10.1055/s-1993-26033

  日期：——

  The reaction of [2,1]benzisoxazole-4,7-quinones 1 and naphth [2,3-c]isoxazole-4,9-quinone 4 with phosphines leads to phosphoranylideneaminoquinones 2 and 5, respectively, in good to excellent yields.

  [2,1]苯并异噁唑-4,7-醌 1 和萘并[2,3-c]异噁唑-4,9-醌 4 与膦反应，可分别生成磷酰亚氨基醌 2 和 5，产率从良好到极佳。
• Torres, Tomas; Eswaran, S.V.; Schaefer, Wolfram, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 701 - 704
  作者：Torres, Tomas、Eswaran, S.V.、Schaefer, Wolfram

  DOI：——

  日期：——
• Torres, Tomas; Eswaran, S.V.; Schaefer, Wolfram, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 705 - 711
  作者：Torres, Tomas、Eswaran, S.V.、Schaefer, Wolfram

  DOI：——

  日期：——
• Unexpected reaction of 2-amino-1,4-naphthoquinone with aldehydes: new synthesis of naphtho[2,1-d]oxazole compounds
  作者：Sam Van Aeken、Jurgen Deblander、Johan De Houwer、Timothy Mosselmans、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.tet.2010.10.082

  日期：2011.1

  Treatment of 3-substituted 2-amino-1,4-naphthoquinones 3 with an aldehyde in a solution of hydrobromic acid in acetic acid led to 2,4-disubstituted naphtho[2,1-d]oxazol-5-ols. The outcome of this simple conversion is even more remarkable in view of the very similar reactions reported in literature, which all give rise to completely different products. Furthermore, the acquired naphthoxazoles 5-11 could be oxidatively ring opened by means of PIFA or CAN into a series of N-acylated 2-amino-1,4-naphthoquinones. A synthetic pathway towards 2-substituted naphtho[2,3-d]oxazole-4,9-diones was also disclosed as the outcome of CAN mediated oxidation of a 4-chloronaphtho[2,1-d]oxazol-5-ol. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.