2-((3-chlorophenyl)amino)naphthalene-1,4-dione | 64505-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((3-chlorophenyl)amino)naphthalene-1,4-dione
• 英文别名: 2-(3-Chloroanilino)-1,4-naphthoquinone；2-(3-chloroanilino)naphthalene-1,4-dione
• CAS: 64505-65-3
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: PEAIHGOMZYGGIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  444.3±45.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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-((3-chlorophenyl)amino)naphthalene-1,4-dione 在 四丁基溴化铵 、 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 2.5h， 生成 1-(3-chlorophenyl)-1,2-dihydrobenzo[g]quinoline-5,10-dione
  参考文献：
  名称：

  An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N-propargylaminonaphthoquinones

  摘要：

  An expedient synthesis of a series of 1,2-dihydrobenzo[g]quinoline-5,10-diones in good yields has been accomplished via three-component one pot sequential reactions of 2-hydroxynaphthalene-1,4-dione, substituted anilines and propargyl as well as 3-ethylpropargyl bromides furnishing N-propargylaminonaphthoquinones, and their concomitant copper(II) triflate-catalyzed intramolecular 6-endo-dig cyclization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.125
• 作为产物：
  描述：

  萘酚 在 2,2-difluoro-5,11-diiodo-6,10-dimethyl-8-phenyl-4,12-bis(2-phenylethenyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene 、 copper diacetate 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.5h， 生成 2-((3-chlorophenyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Bodipy Derivatives as Organic Triplet Photosensitizers for Aerobic Photoorganocatalytic Oxidative Coupling of Amines and Photooxidation of Dihydroxylnaphthalenes

  摘要：

  We used iodo-Bodipy derivatives that show strong absorption of visible light and long-lived triplet excited states as organic catalysts for photoredox catalytic organic reactions. Conventionally most of the photocatalysts are based on the off-the-shelf compounds, usually showing weak absorption in the visible region and short triplet excited state lifetimes. Herein, the organic catalysts are used for two photocatalyzed reactions mediated by singlet oxygen (O-1(2)), that is, the aerobic oxidative coupling of amines and the photooxidation of dihydroxylnaphthalenes, which is coupled to the subsequent addition of amines to the naphthoquinones, via C-H functionalization of 1,4-naphthoquinone, to produce N-aryl-2-amino-1,4-naphthoquinones (one-pot reaction), which are anticancer and antibiotic reagents. The photoreactions were substantially accelerated with these new iodo-Bodipy organic photocatalysts compared to that catalyzed with the conventional Ru(II)/Ir(III) complexes, which show weak absorption in the visible region and short-lived triplet excited states. Our results will inspire the design and application of new organic triplet photosensitizers that show strong absorption of visible light and longlived triplet excited state and the application of these catalysts in photoredox catalytic organic reactions.

  DOI：

  10.1021/jo400769u

文献信息

• Exploration of Benzo[b]carbazole-6,11-diones as anticancer agents: Synthesis and studies of hTopoIIα inhibition and apoptotic effects
  作者：Shailendra Sisodiya、Subarno Paul、Hiteshkumar Chaudhary、Preeti Grewal、Gulshan Kumar、Divine P Daniel、Biswajit Das、Deepika Nayak、Sankar K. Guchhait、Chanakya N. Kundu、Uttam C. Banerjee

  DOI：10.1016/j.bmcl.2021.128274

  日期：2021.10

  cells (MCF 10A). Some of the active compounds were evaluated for clonogenic cell survival and apoptotic effects in cancer cells (DAPI nuclear staining, Comet assay, Annexin-V-FITC/PI dual staining, flow cytometry, and western blot analysis with relevant proteins). All compounds were tested for hTopoIIα inhibitory activity. The investigated series compounds showed important properties like significant

  两个系列的（杂）芳基氨基萘醌和苯并稠合咔唑醌被考虑用于研究，理由是相关的结构基序存在于许多药物、临床试验药物、天然产物和 hTopoIIα 抑制剂中。通过脱氢C N 和Pd催化C反应共合成42种化合物C 键形成转换。这些化合物针对多种癌细胞进行了筛选，包括高度转移的癌细胞（MCF-7、MDA-MB-231、H-357 和 HEK293T）和正常细胞（MCF 10A）。评估了一些活性化合物在癌细胞中的克隆形成细胞存活和细胞凋亡效应（DAPI 核染色、彗星试验、膜联蛋白-V-FITC/PI 双染色、流式细胞术和相关蛋白质的蛋白质印迹分析）。测试所有化合物的 hTopoIIα 抑制活性。研究的系列化合物显示出重要的特性，例如在 S 期细胞周期停滞的癌细胞中显着的细胞凋亡抗增殖和下调 NF-κβ 信号级联，对正常细胞的细胞毒性相对较小，与抗癌药物依托泊苷相比，抑制 hTopoIIα 的效率更高.
• <i>t</i>-BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines
  作者：Yu Dong、Ting Mei、Qi-Qi Luo、Qiang Feng、Bo Chang、Fan Yang、Hong-wei Zhou、Zhi-Chuan Shi、Ji-Yu Wang、Bing He

  DOI：10.1039/d1ra00193k

  日期：——

  3-indolylnaphthoquinones with amines, such as various (hetero)aromatic amine and aliphatic amine via t-BuOK-mediated oxidative coupling at room temperature has been developed. This reaction provides efficient access to the biologically important and synthetically useful 2-amino-1,4-naphthoquinones and 2-amino-3-indolylnaphthoquinones with good yields under mild conditions. The present protocol is simple

  1,4-萘醌和相关的 3-吲哚基萘醌与胺（例如各种（杂）芳香胺和脂肪胺）在室温下通过 t -BuOK 介导的氧化偶联进行无过渡金属胺化。该反应可以在温和条件下以良好的收率有效地获得具有重要生物学意义和合成用途的2-氨基-1,4-萘醌和2-氨基-3-吲哚基萘醌。本方案简单实用，具有良好的官能团耐受性。此外，将所得2-氨基-3-吲哚基萘醌进一步转化合成多环N-杂环。
• A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water
  作者：Ji-Yu Wang、Xu-Ling Chen、Yu Dong、Shuai He、Rui Zhang、Hua Zhang、Lei Tang、Xiao-Mei Zhang

  DOI：10.1055/s-0037-1610689

  日期：2019.3

  A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated

  已开发出从 1,4-萘醌和硝基化合物在水中一锅法合成 2-(N-取代氨基)-1,4-萘醌。该方法的特点是反应条件温和，提供具有各种官能团的芳香硝基化合物，如卤素、甲硫基、酯、酰胺，甚至烯丙基、炔丙基和杂环，以及耐受性良好的脂肪族硝基化合物。该方法可以扩大规模，我们将获得的 2-(N-取代氨基)-1,4-萘醌进一步转化以合成咔唑醌衍生物。
• Cu-Catalysed synthesis of benzo[<i>f</i>]indole-2,4,9(3<i>H</i>)-triones by the reaction of 2-amino-1,4-napthoquinones with α-bromocarboxylates
  作者：Fazhou Yang、Ziyan Liu、Hao Liu、Yu Shangguan、Hao Deng、Jiaxing Huang、Yumei Xiao、Hongchao Guo、Cheng Zhang

  DOI：10.1039/d0ob00291g

  日期：——

  Cu-Catalysed oxidant-free cascade ester amidation/radical cyclization of 2-amino-1,4-napthoquinones with α-bromocarboxylates to afford benzo[f]indole-2,4,9(3H)-triones.

  使用Cu催化剂，无氧氧化剂的情况下，将2-氨基-1,4-萘醌与α-溴羧酸酯进行级联酯胺化/自由基环化反应，得到苯并[f]吲哚-2,4,9(3H)-三酮。
• Copper-Catalyzed Three-Component Difunctionalization of Aromatic Alkenes with 2-Amino-1,4-naphthoquinones and α-Bromocarboxylates
  作者：Yu Shangguan、Fazhou Yang、Hao Deng、Hao Liu、Ziyan Liu、Wanyue Zhuang、Chenxi Qiao、Aizheng Wang、Yumei Xiao、Cheng Zhang

  DOI：10.1021/acs.joc.9b01082

  日期：2019.9.6

  that the difunctionalization reaction is accompanied by ester exchange reaction with the solvent. In this method, α-bromocarboxylates are used as radical precursors and 2-amino-1,4-naphthoquinones as radical trapping reagents. The substrate scope is broad because various aromatic alkenes, 2-amino-1,4-naphthoquinones, and α-bromocarboxylates are employed in the reaction, and corresponding products are

  描述了铜催化的芳香族烯烃的三组分双官能化，以得到具有不同结构的1,4-萘醌衍生物。实验表明，双官能化反应伴随着与溶剂的酯交换反应。在该方法中，将α-溴代羧酸盐用作自由基前体，将2-氨基-1,4-萘醌用作自由基捕获剂。底物范围宽，因为在反应中使用了各种芳族​​烯烃，2-氨基-1,4-萘醌和α-溴代羧酸盐，并且以中等至良好的产率获得了相应的产物。