2-hydroxy-6,7-dimethoxy-3-(2-nitrophenyl)-1,4-naphthoquinone | 221189-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-6,7-dimethoxy-3-(2-nitrophenyl)-1,4-naphthoquinone
• 英文别名: 6,7-dimethoxy-2-(2-nitrophenyl)-3-hydroxy-1,4-naphthoquinone
• CAS: 221189-56-6
• 化学式: C₁₈H₁₃NO₇
• 分子量: 355.304
• InChiKey: SLUFELHGSORLQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  115.97
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6,7-dimethoxy-3-(2-nitrophenyl)-1,4-naphthoquinone 在 platinum(IV) oxide air 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成 11H-2,3-dimethoxybenzocarbazole-5,6-dione
  参考文献：
  名称：

  A Simple Synthesis of Benzocarbazolequinones via o-Nitroarylation of 2-Hydroxy-1,4-naphthoquinones

  摘要：

  The reaction of 2-hydroxy-1,4-naphthoquinones (la-c) with o-fluoronitrobenzenes (2a,b) in the presence of K2CO3 in DMSO at 100 degrees C gave 2-hydroxy-3-(2-nitroaryl)-1,4-naphthoquinones (3a-e) in moderate to fair yields, which in turn were transformed into the corresponding 11H-benzo[a] carbazole-5,6-dione (6a-e) and SH-benzo[b]carbazole-6, 11-dione (7a-e) derivatives in good yields by catalytic hydrogenation over PtO2 in AcOEt at room temperature and 1 atm, followed by exposure to air and then heating at reflux temperature.

  DOI：

  10.3987/com-98-8364
• 作为产物：
  描述：

  2-(2-乙酰基-4,5-二甲氧基苯基)乙酸甲酯 在 sodium hydroxide 、 硫酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 生成 2-hydroxy-6,7-dimethoxy-3-(2-nitrophenyl)-1,4-naphthoquinone
  参考文献：
  名称：

  钯介导的邻乙酰基苯乙酸的全合成：吲哚[2,3 - b ]萘-6,11-二酮的一般路线

  摘要：

  在这里，我们描述了一种新的，有效的一般合成ö -acetylphenylacetic酸由赫克钯催化的芳基化Ñ丁基乙烯基醚与ö -bromophenylacetic酸，并将其应用到吲哚并[2,3-的合成b ]萘-6- ，11-二酮。

  DOI：

  10.1016/s0040-4039(01)00884-x

文献信息

• Palladium-catalyzed synthesis of o-acetylbenzoic acids: a new, efficient general route to 2-hydroxy-3-phenyl-1,4-naphthoquinones and indolo[2,3-b]naphthalene-6,11-diones
  作者：José C Barcia、Jacobo Cruces、Juan C Estévez、Ramón J Estévez、Luis Castedo

  DOI：10.1016/s0040-4039(02)00990-5

  日期：2002.7

  here a new, efficient general synthesis of o-acetylbenzoic acids by Heck palladium-catalyzed arylation of n-butyl vinyl ether with o-bromobenzoic acid esters and the use of these compounds as starting materials for the synthesis of 3-benzylideneisochroman-1,4-diones, which readily rearrange to 2-hydroxy-3-phenyl-1,4-naphthoquinones. The application of this strategy to the synthesis of indolo[2,3-b]naphthalene-6

  我们在这里描述了一种新的，高效的，一般的合成方法，该方法通过Heck钯催化的正丁基乙烯基醚与邻溴代苯甲酸酯的芳基化反应来合成邻乙酰基苯甲酸，并将这些化合物用作合成3-苄叉基异色满1的原料，4-二酮，其容易重排为2-羟基-3-苯基-1，4-萘醌。还描述了该策略在吲哚[2，3 - b ]萘-6，11-二酮合成中的应用。
• Gold-Facilitated ‘6-Exo-dig’ Intramolecular Cyclization of 2-[(2-Nitrophenyl)ethynyl]phenylacetic Acids: General Access to 5H-Benzo[b]carbazole-6,11-diones
  作者：Ramón Estévez、Cristian Salas、Francisco Reboredo、Juan Estévez、Ricardo Tapia

  DOI：10.1055/s-0029-1218362

  日期：2009.12

  The preliminary results of a regiospecific synthesis of (Z)-1-(2-nitrobenzylidene)isochroman-3-ones by gold(I)-catalyzed cycloisomerization of phenylethynylacetic acids under mild conditions is described. These novel lactones proved to be suitable starting materials for a new, general access to 5H-benzo[b]carbazole-6,11-diones.

  本文介绍了在温和条件下通过金（I）催化苯乙炔基乙酸的环异构化反应，以区域特异性合成 (Z)-1-(2-nitrobenzylidene)isochroman-3-ones 的初步结果。这些新型内酯被证明是一种新的、通用的 5H-苯并[b]咔唑-6,11-二酮的合适起始原料。
• From phenylacetylphenylacetic acids to indoles: a simple new divergent synthesis of 6,11-dihydro-5H-benzo[a]carbazol-5,6-diones and 6,11-dihydro-5H-benzo[b]carbazol-6,11-diones
  作者：Jacobo Cruces、Elena Martı́nez、Mónica Treus、Luis A Martı́nez、Juan C Estévez、Ramón J Estévez、Luis Castedo

  DOI：10.1016/s0040-4020(02)00192-8

  日期：2002.4

  The synthesis 6,11-dihydro-5H-benzo[a]carbazole-5,6-diones and 6,11-dihydro-5H-benzo[b]carbazole-6,11-diones from common starting materials, 1-(2'-nitrophenylacetyl)phenylacetic acids is described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium mediated total synthesis of o-acetylphenylacetic acids: a general route to indolo[2,3-b]naphthalene-6,11-diones
  作者：Jacobo Cruces、Juan C Estévez、Luis Castedo、Ramón J Estévez

  DOI：10.1016/s0040-4039(01)00884-x

  日期：2001.7

  Here we describe a new, efficient general synthesis of o-acetylphenylacetic acids by Heck palladium-catalyzed arylation of n-butyl vinyl ether with o-bromophenylacetic acids, and its application to the synthesis of indolo[2,3-b]naphthalene-6,11-diones.

  在这里，我们描述了一种新的，有效的一般合成ö -acetylphenylacetic酸由赫克钯催化的芳基化Ñ丁基乙烯基醚与ö -bromophenylacetic酸，并将其应用到吲哚并[2,3-的合成b ]萘-6- ，11-二酮。
• A Simple Synthesis of Benzocarbazolequinones via o-Nitroarylation of 2-Hydroxy-1,4-naphthoquinones
  作者：Kazuhiro Kobayashi、Tetsuya Taki、Masataka Kawakita、Masaharu Uchida、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.3987/com-98-8364

  日期：——

  The reaction of 2-hydroxy-1,4-naphthoquinones (la-c) with o-fluoronitrobenzenes (2a,b) in the presence of K2CO3 in DMSO at 100 degrees C gave 2-hydroxy-3-(2-nitroaryl)-1,4-naphthoquinones (3a-e) in moderate to fair yields, which in turn were transformed into the corresponding 11H-benzo[a] carbazole-5,6-dione (6a-e) and SH-benzo[b]carbazole-6, 11-dione (7a-e) derivatives in good yields by catalytic hydrogenation over PtO2 in AcOEt at room temperature and 1 atm, followed by exposure to air and then heating at reflux temperature.