2-(甲基氨基)萘-1,4-二酮 | 14423-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(甲基氨基)萘-1,4-二酮
• 英文名称: 2-(methylamino)-1,4-naphthoquinone
• 英文别名: 2-(methylamino)naphthalene-1,4-dione；1,4-Naphthalenedione, 2-(methylamino)-
• CAS: 14423-00-8
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: FEWFXZPGPSWQJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(甲基氨基)萘-1,4-二酮 在 potassium carbonate 、 morpholine-iodine complex 作用下， 以 水 为溶剂， 反应 2.0h， 以54%的产率得到2-iodo-3-(methylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of indolequinones via a Sonogashira coupling/cyclization cascade reaction

  摘要：

  A mild strategy for constructing indolequinone motifs is described on the basis of the Sonogashira reaction and a copper-catalyzed intramolecular cyclization cascade reaction. The first step involves the palladium- and copper-catalyzed reaction between halogenated naphthoquinone and terminal acetylene to generate a coupling product, which then reacts in a copper-catalyzed intramolecular cyclization with the nitrogen functional group adjacent to the carbon-carbon triple bond. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.008
• 作为产物：
  描述：

  6-Hydroxy-4-methyl-1H-naphth<2.1-d><1.3>oxazin-3(3H)-one 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到2-(甲基氨基)萘-1,4-二酮
  参考文献：
  名称：

  p-Quinonemethide Analog of the CC-1065 and Duocarmycin Alkylation Subunits

  摘要：

  The synthesis and preliminary evaluation of 10 and 11, stable precursors to the inherently reactive but isolable p-quinonemethide analog 9 of the CC-1065 and duocarmycin alkylation subunits, are detailed. The p-quinonemethide 9, while reactive (t(1/2) < 1 min, CH3OH), represents one of the few unsubstituted quinonemethides sufficiently stable for isolation and characterization. The structural origin of this stability and the ramifications of the observations on the origin of the stability of the CC-1065 and duocarmycin alkylation subunits are discussed.

  DOI：

  10.1021/jo00096a043

文献信息

• Chinon-Amin-Reaktionen, 20. Mitt. 1,4-Naphthochinon-Derivate einiger Psychopharmaka mit sekundärer Aminstruktur
  作者：Hans-Jörg Kallmayer、Christiane Tappe

  DOI：10.1002/ardp.19863190708

  日期：——

  Missing.

  丢失的。
• ON THE REACTION OF PRIMARY ALIPHATIC AMINES WITH 1,2-NAPHTHOQUINONE-4-SULFONIC ACID
  作者：Klaus Hartke、Ulrike Lohmann

  DOI：10.1246/cl.1983.693

  日期：1983.5.5

  Primary amines react with 1,2-naphthoquinone-4-sulfonic acid to form violet dyes in a complex redox reaction. Their general structure 6 has been established by an independent synthesis.

  伯胺与 1,2-萘醌-4-磺酸反应，在复杂的氧化还原反应中形成紫色染料。它们的通用结构 6 已通过独立合成确定。
• Iodine mediated reaction of quinones and N-substituted amino esters to 2-substituted benzo[f]isoindole-4,9-diones
  作者：Yu-jin Li、Huan-ming Huang、Jie Ju、Jian-hong Jia、Liang Han、Qing Ye、Wu-bin Yu、Jian-rong Gao

  DOI：10.1039/c3ra44095h

  日期：——

  A novel and efficient synthesis of benzo[f]isoindole-4,9-diones through the I2-promoted cyclization reaction of N-substituted amino acid esters and quinones has been realized successfully via an unprecedented 1,3-dipolar cycloaddition using KF as the base. Different substituted amino esters were found able to react with quinones through a cycloaddition reaction to afford 2-substituted benzo[f]isoindole-4

  苯并[一种新颖和有效的合成˚F ]通过I异吲哚-4,9-二酮2的促进的环化反应Ñ取代的氨基酸酯和醌已经成功地实现了通过使用KF作为一个前所未有的1,3-偶极环加成基地。发现不同的取代的氨基酯能够通过环加成反应与醌反应，得到2-取代的苯并[ f ]异吲哚-4，9-二酮。这些令人感兴趣的化合物的出人意料的，短暂的，有吸引力的和直接的合成是重要和相关的，并且为合成2-取代的苯并[ f ]异吲哚-4,9-二酮提供了极其优选的方法。
• Solvent effects on the oxidative free radical reactions of 2-amino-1,4-naphthoquinones
  作者：Chao-Ming Tseng、Yi-Lung Wu、Che-Ping Chuang

  DOI：10.1016/j.tet.2004.10.029

  日期：2004.12

  Solvent effects on the manganese (III) initiated oxidative free radical reactions of 2-amino-1,4-naphthoquinones are described. This free radical reaction provides a novel method for the synthesis of benzo[f]indole-4,9-diones, benzo[f]indole-2,4,9-triones, benzo[b]carbazole-6,11-diones and benzo[b]acridine-6,11-diones. High chemoselectivity was observed in different solvents.

  描述了溶剂对2-氨基-1,4-萘醌的锰（III）引发的氧化自由基反应的影响。该自由基反应为合成苯并[ f ]吲哚-4,9-二酮，苯并[ f ]吲哚-2,4,9-三酮，苯并[ b ]咔唑-6,11-二酮和苯并[ b ] ac啶-6,11-二酮。在不同溶剂中观察到高化学选择性。
• Oxidative free radical reactions between 2-amino-1,4-naphthoquinones and carbonyl compounds
  作者：Yi-Lung Wu、Che-Ping Chuang、Pi-Yun Lin

  DOI：10.1016/s0040-4020(01)00480-x

  日期：2001.6

  initiated oxidative free radical reaction provides a novel method for the synthesis of benzo[f]indole-4,9-diones from 2-amino-1,4-naphthoquinones and carbonyl compounds. The regioselectivity of this reaction was also studied with unsymmetrical ketones from which both isomeric indoles 10 and 11 were formed. With α-halo, α-phenoxy and α-methanesulfonyl ketones, in most cases, this reaction gave high

  锰（III）引发的氧化自由基反应提供了一种从2-氨基-1,4-萘醌和羰基化合物合成苯并[ f ]吲哚-4,9-二酮的新方法。还用不对称酮研究了该反应的区域选择性，所述不对称酮由其形成异构体吲哚10和11。在大多数情况下，对于α-卤代，α-苯氧基和α-甲磺酰基酮，该反应具有很高的区域选择性。用2-烷基取代的1，3-二酮14，获得吲哚11作为唯一产物。