碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子 | 117560-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子
• 英文名称: 2-oxido-3-phenyliodonio-1,4-naphthoquinone
• 英文别名: 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide；3-(phenyl-λ3-iodanylidene)naphthalene-1,2,4-trione
• CAS: 117560-06-2
• 化学式: C₁₆H₉IO₃
• 分子量: 376.15
• InChiKey: NGPXFOVGRSLWGC-UHFFFAOYSA-N

物化性质

• 熔点：
  >320 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子 在 氢碘酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以77%的产率得到2-hydroxy-3-iodo-1,4-naphthoquinone
  参考文献：
  名称：

  Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone

  摘要：

  Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.04.034
• 作为产物：
  描述：

  碘苯二乙酸 、 2-hydroxy-1,4-naphthoquinone 在 sodium carbonate 作用下， 以 水 为溶剂， 生成 碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子
  参考文献：
  名称：

  通过环状碘鎓叶立德策略催化环状 1,3-二羰基的无碱 Suzuki 型 α-芳基化

  摘要：

  环状 1,3-二羰基的通用催化 α-芳基化已经开发出来，为获得各种高价值的 2-芳基（杂）环 1,3-二羰基提供了便利。成功的关键是通过环状碘叶立德策略。我们的方法是无碱基的，并且具有广泛的底物范围（> 100 个示例）。重要的是，我们的方法允许后期修改并显着简化先前的合成。

  DOI：

  10.1002/anie.202400741

文献信息

• A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds
  作者：Konstantina Spagou、Elizabeth Malamidou-Xenikaki、Spyros Spyroudis

  DOI：10.3390/10010226

  日期：——

  The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.

  2-羟基-1,4-萘醌的苯基碘鎓叶立德与氨基酯、脲、氨基醇和氨基酚在回流的二氯甲烷中反应，以良好的产率得到吲哚二酮2-酰胺化合物，其在溶液中以烯醇酰胺形式存在。在铜催化的反应中，同样的反应物主要得到相应的N-芳基化合物。芳基肼主要被叶立德氧化，芳基化仅在低产率下发生。
• METHOD FOR PRODUCING 2-ALKYLCARBONYLNAPHTHO[2,3-b]FURAN-4,9-DIONE-RELATED SUBSTANCE, AND SAID RELATED SUBSTANCE
  申请人：Sumitomo Dainippon Pharma Co., Ltd.

  公开号：US20190062294A1

  公开（公告）日：2019-02-28

  Provided is a method for producing a 2-alkylcarbonylnaphtho[2,3-b]furan-4,9-dione-related substance, which is suitable for the production on an industrial scale. The present invention provides: a method for producing an intermediate for the production of a 2-alkylcarbonyl[2,3-b]furan-4,9-dione, which comprises reacting a 1-butyne derivative in which a ketone or an alcohol is protected with a 2-hydroxy-1,4-naphthoquinone derivative having a leaving group at position-3 in a solvent in the presence of a metal or a metal compound and a base; and a substance relating to the intermediate.

  提供了一种用于生产与2-烷基碳酰萘[2,3-b]呋喃-4,9-二酮相关的物质的方法，该方法适合于工业规模生产。本发明提供：一种用于生产2-烷基碳酰[2,3-b]呋喃-4,9-二酮的中间体的生产方法，该方法包括在溶剂中，在金属或金属化合物和碱的存在下，将含有酮或醇的1-丁炔衍生物与在3位具有离去基团的2-羟基-1,4-萘醌衍生物反应；以及与中间体相关的物质。
• A novel series of napabucasin derivatives as orally active inhibitors of signal transducer and activator of transcription 3 (STAT3)
  作者：Chungen Li、Caili Chen、Qi An、Tao Yang、Zitai Sang、Yang Yang、Yuan Ju、Aiping Tong、Youfu Luo

  DOI：10.1016/j.ejmech.2018.10.067

  日期：2019.1

  than napabucasin. Treatment with compound 8q decreased protein expression level of total STAT3 and p-STAT3Y705 in vitro. The binding of compound 8q with STAT3 were further validated by electrophoretic mobility shift assay and surface plasmon resonance analysis. Compound 8q has a KD of 110.2 nM for full-length STAT3 recombinant protein. Moreover, the aqueous solubility of 8q was over 4.5-fold than that

  转录因子STAT3是多种癌症治疗的引人注目的靶标。Napabucasin在III期临床试验中用于治疗多种癌症，通过靶向STAT3被认为是最有前途的抗癌药物之一。本文中，设计并合成了一系列新的纳布卡辛衍生物，它们对多种癌细胞均具有有效的抑制活性。在衍生物中，化合物8q对U251，HepG2，HT29和CT26细胞表现出有效的抑制活性，IC 50值分别为0.22、0.49、0.07和0.14μM，比那巴布星的效力高10倍以上。用化合物治疗8Q降低总STAT3和对STAT3的蛋白质表达水平Y705 体外。化合物8q与STAT3的结合进一步通过电泳迁移率变动分析和表面等离子体共振分析进行了验证。对于全长STAT3重组蛋白，化合物8q的K D为110.2 nM。此外，8q的水溶解度是那巴布星的4.5倍以上。此外，与未经治疗的小鼠相比，体内化合物8q 显着降低了肿瘤的生长，并显示出良好的安全性，表明其作为肿瘤治疗有效候选药物的巨大潜力。
• Functionalized Hydroxyquinones through Suzuki-Type Coupling of Phenyliodonium Ylides of Hydroxyquinones with Arylboronic Acids
  作者：Spyros Spyroudis、Georgia Kazantzi、Elizabeth Malamidou-Xenikaki

  DOI：10.1055/s-2006-950447

  日期：2006.9

  The palladium(II) acetate catalyzed reaction of phenyliodonium ylides of 2-hydroxyquinones with arylboronic acids affords a variety of 3-substituted 2-hydroxyquinone derivatives. Best yields are obtained by using tri(tert-butyl)phosphine as a ligand.

  乙酸钯 (II) 催化 2-羟基醌的苯基碘鎓叶立德与芳基硼酸反应得到多种 3-取代的 2-羟基醌衍生物。使用三（叔丁基）膦作为配体可获得最佳产率。
• Regiospecific Synthesis of Unsymmetrical 2,3-Diarylquinones via Stepwise Pd(0)-Catalyzed Couplings of Arylstannanes to Doubly Activated Quinone Equivalents
  作者：Kenneth W. Stagliano、Helena C. Malinakova

  DOI：10.1016/s0040-4039(97)01532-3

  日期：1997.9

  Coupling of aryltaannanes to 2-phenyliodonio-1,4-naphthoquinone-3-oxide in the presence of a tetrakis(triphenylphosphine)palladium(0)-cuprous iodide catalyst yields 3-aryl-2-hydroxy-1,4-naphthoquinones which are converted to the corresponding 3-aryl-2-trifluoromethanesulfonyloxy-1,4-naphthoquinone and coupled to a different arylstannane to yield unsymmetrical 2,3-diaryl-1,4-naphthoquinones in good

  在四（三苯基膦）钯（0）​​-碘化亚铜催化剂存在下，芳基金刚烷与2-苯基碘代-1,4-萘醌-3-氧化物的偶合反应生成3-芳基-2-羟基-1,4-萘醌转化为相应的3-芳基-2-三氟甲磺酰氧基-1，4-萘醌，并偶联到不同的芳基锡烷上，以良好的收率得到不对称的2，3-二芳基-1，4-萘醌。©1997爱思唯尔科学有限公司。