2-溴-3-(甲基氨基)-1,4-萘二酮 | 91182-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴-3-(甲基氨基)-1,4-萘二酮
• 中文别名: 2-羟基-3-[3-(三羟基甲硅烷基)丙氧基]丙烷-1-磺基酸
• 英文名称: 2-bromo-3-methylamino-1,4-naphthoquinone
• 英文别名: 1,4-Naphthalenedione, 2-bromo-3-(methylamino)-；2-bromo-3-(methylamino)naphthalene-1,4-dione
• CAS: 91182-56-8
• 化学式: C₁₁H₈BrNO₂
• 分子量: 266.094
• InChiKey: OXCKULWCKUNSQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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-溴-3-(甲基氨基)-1,4-萘二酮 在 吡啶 、 copper(I) oxide 、 palladium diacetate 、 3-丁炔-2-醇 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-(1-hydroxyethyl)-1-methyl-1H-benzo[ f ]indole-4,9-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：

  2,3-二溴-1,4-萘醌 以 二氯甲烷 、 氯仿 为溶剂， 反应 22.0h， 生成 2-溴-3-(甲基氨基)-1,4-萘二酮
  参考文献：
  名称：

  醌胺反应，第 21 部分。1) 一些 2-amino-3-halogen-1,4-naphthoquinones 的光反应性

  摘要：

  2.3-dichloro 和 2.3-dibromo-1.4-naphthoquinone 与 胺地昔帕明 (A)、去甲替林 (B、C)、马普替林 (D) 和苯并辛胺 (E) 对应的 2-氨基-3-氯和 2-氨基-3-溴-1,4-萘醌 2a - e 和 5a-e 已实施。而日光仅使氯化氨基醌 2 的胺官能团脱烷基化，而在溴化氨基醌 5 的情况下，与胺相邻的 C-3 优选脱溴化。令人惊奇的是，脱溴产物的胺官能团在日光下不再脱烷基。

  DOI：

  10.1002/ardp.19863190905

文献信息

• 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。
• Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C−H Halogenation
  作者：Pallaba Ganjan Dalai、Kuntal Palit、Niranjan Panda

  DOI：10.1002/adsc.202101291

  日期：2022.3

  A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C−H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur ylide, which undergoes pyrolytic elimination of ethylene by affording halonium ions. These ions were accumulated and stabilized by DMSO through coordination

  报道了一种通过 1,2-二卤代乙烷 (hal=Br, I) 和二甲基亚砜 (DMSO) 的反应生成卤素阳离子池的方法，用于芳烃和杂芳烃的 C-H 卤化。DMSO 和 1,2-二卤代乙烷的初始反应生成硫叶立德，其通过提供卤离子来热解消除乙烯。DMSO 通过配位形成卤化反应的卤离子池，从而积累和稳定这些离子。该方案在室温下对芳烃的亲电单卤化具有选择性；但是，通过提高反应温度会形成多卤代产物。杂芳烃和一些常用药物的后期卤化表明该协议在药物化学中的合成效用。与经典方法不同，
• One-Step Synthesis of 1,2,3,4-Tetrahydrobenzo(g)quinazoline-5,10-dione Derivatives from Vitamin K3.
  作者：Shunsaku OHTA、Yasunari HINATA、Masayuki YAMASHITA、Ikuo KAWASAKI、Yoko JINDA、Shinobu HORIE

  DOI：10.1248/cpb.42.1730

  日期：——

  The reactions of 2-halogenonaphthoquinones (5, 13, 14 and 15) and 2-methyl-1, 4-naphthoquinone (20; vitamin K3) with primary and secondary amines were examined. 1, 3-Dialkyl-1, 2, 3, 4-tetrahydrobenzo[g]quinazoline-5, 10-diones (9) were obtained in moderate yields by treating 20 with formaldehyde in primary amines. A plausible reaction path-way is also presented.

  对2-卤代萘醌（5、13、14和15）和2-甲基-1,4-萘醌（20；维生素K3）与一级和二级胺的反应进行了研究。通过在一级胺中用甲醛处理20，获得了1,3-二烷基-1,2,3,4-四氢苯并[g]喹唑啉-5,10-二酮（9），产率适中。同时也提出了一个合理的反应路径。
• One-Pot Synthesis of Benzo[f]indole-4,9-diones from 1,4-Naphthoquinones and Terminal Acetylenes
  作者：Mitsuaki Yamashita、Kazunori Ueda、Koichi Sakaguchi、Harukuni Tokuda、Akira Iida

  DOI：10.1248/cpb.59.1289

  日期：——

  In this paper, a concise one-pot method for the construction of benzo[f]indole-4,9-dione motifs is described. These transformations proceed via a sequential palladium- and copper-catalyzed coupling reaction of 1,4-naphthoquinones with terminal acetylenes, followed by a copper-catalyzed intramolecular cyclization reaction of the resulting coupling product.

  本文介绍了一种构建苯并[f]吲哚-4,9-二酮基团的简便的一锅法。这些转化是通过钯和铜催化的 1,4-萘醌与末端乙炔的连续偶联反应进行的，然后是铜催化的偶联产物的分子内环化反应。
• The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors
  作者：Cláudia Valente、Rui Moreira、Rita C. Guedes、Jim Iley、Mohammed Jaffar、Kenneth T. Douglas

  DOI：10.1016/j.bmc.2007.04.068

  日期：2007.8

  A series of 1,4-naphthoquinone derivatives diversely substituted at C-2, C-3, C-5 and C-8, prepared by reaction of amines, amino acids and alcohols with commercial 1,4-naphthoquinones, has been evaluated against papain and bovine spleen cathepsin B. These 1,4-naphthoquinone derivatives were found to be irreversible inhibitors for both cysteine proteases, with second-order rate constants, k(2), ranging from 0.67 to 35.4 M-1 s(-1) for papain, and from 0.54 to 8.03 M-1 s(-1) for cathepsin B. Some derivatives display a hyperbolic dependence of the first-order inactivation rate constant, k(obs) with the inhibitor concentration, indicative of a specific interaction process between enzyme and inhibitor. The chemical reactivity of the compounds towards cysteine as a model thiol is dependent on the naphthoquinone LUMO energy, whereas papain inactivation is not. The 1,4-naphthoquinone derivatives are inactive against the serine protease, porcine pancreatic elastase. (c) 2007 Elsevier Ltd. All rights reserved.