5-nitro-3-phenylisocoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 5-nitro-3-phenylisocoumarin
• 英文别名: 5-Nitro-3-phenylisochromen-1-one
• 化学式: C₁₅H₉NO₄
• 分子量: 267.241
• InChiKey: ARAHTIHEHCHBOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-3-phenylisocoumarin 在 氨 作用下， 以 乙二醇甲醚 为溶剂， 反应 4.0h， 以73%的产率得到5-nitro-3-phenylisoquinolin-1-one
  参考文献：
  名称：

  [EN] TANKYRASE INHIBITORS
  [FR] INHIBITEURS DE TANKYRASE

  摘要：

  本发明涉及一种具有式I的化合物，其中X为C(R6)或N，Y为C或N，环A、环B、R1和R2具有本文中定义的含义，前提是当环B为碳环时，X为C(R6)；或其药学上可接受的盐或溶剂。这些化合物是坦克酶-1和坦克酶-2抑制剂，并可用于治疗多种疾病，包括癌症。

  公开号：

  WO2014087165A1
• 作为产物：
  描述：

  3-硝基邻苯二甲酸 在 ammonium hydroxide 、 sodium hydroxide 、 copper(l) iodide 、 mercury(II) diacetate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 100.25h， 生成 5-nitro-3-phenylisocoumarin
  参考文献：
  名称：

  5-Nitroisocoumarins from tandem Castro–Stephens coupling—6-endo-dig cyclisation of 2-iodo-3-nitrobenzoic acid and arylethynes and ring-closure of methyl 2-alkynyl-3-nitrobenzoates with electrophiles

  摘要：

  Reaction of 2-iodo-3-nitrobenzoic acid with arylalkynyl copper(I) reagent gave 3-aryl-5-nitroisocoumarins. Castro-Stephens coupling was followed by in situ Cu-catalysed ring-closure. H-1 NMR and X-ray crystallography showed the cyclisations to be 6-endo, contrasting with reports of 5-exo cyclisation of analogous 2-iodobenzoate esters with alkynes. Sonogashira couplings of methyl 2-iodo-3-nitro-benzoate with phenylacetylene and with trimethylsilylacetylene gave the corresponding 2-alkynyl-3-nitrobenzoate esters. With HgSO4, the phenylalkyne underwent 6-endo cyclisation to give 5-nitro-3-phenylisocoumarin. The disubstituted alkyne esters gave 4-phenylselenylisocoumarins with PhSeCl. 5-Nitro-3-phenyl-4-phenylselenylisocoumarin shows significant sterically-driven distortion of the isocoumarin ring. Reaction of methyl 3-nitro-2-phenylethynylbenzoate with ICI gave the 4-iodoisocoumarin. Thus the nitro group tends to direct these electrophile-driven cyclisations towards the 6-endo mode. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.005

文献信息

• Super acid catalysed sequential hydrolysis/cycloisomerization of o-(acetylenic)benzamides under microwave condition: Synthesis, antinociceptive and antiinflammatory activity of substituted isocoumarins
  作者：CHANDRASEKARAN PRAVEEN、P DHEENKUMAR、P T PERUMAL

  DOI：10.1007/s12039-012-0325-2

  日期：2013.1

  Synthesis of isocoumarins and related compounds via triflic acid promoted hydrolysis/cyclization sequence of 2-(alkynyl)benzamides under microwave condition was achieved. The substrate scope of the reaction was broad to include not only aromatic but also polyaromatic and heteroaromatic motifs, thus highlighting the significance of this methodology. One-pot operation, short reaction time, good chemical

  在微波条件下，通过三氟甲磺酸促进了2-（炔基）苯甲酰胺的水解/环化序列，合成了异香豆素及相关化合物。反应的底物范围很广，不仅包括芳族基团，还包括聚芳族和杂芳族基序，因此突出了该方法的重要性。一锅操作，短反应时间，良好的化学收率和出色的区域选择性是该方案的优点。使用体内啮齿动物模型评估所有合成的化合物的抗伤害感受和抗炎活性。 在微波条件下，通过三氟甲磺酸合成异香豆素促进了2-（炔基）苯甲酰胺的顺序水解/环化。使用体内啮齿动物模型评估所有合成的化合物的抗伤害感受和抗炎活性。
• Formation of 3-Aryl-5-nitroisocoumarins from 5-Nitroisocoumarins and Aromatic Acyl Chlorides under Friedel−Crafts Conditions
  作者：Peter T. Sunderland、Andrew S. Thompson、Michael D. Threadgill

  DOI：10.1021/jo0711236

  日期：2007.9.1

  Treatment of 5-nitroisocoumarin with aromatic acyl chlorides under Friedel−Crafts conditions gives 3-aryl-5-nitroisocoumarins, rather than the expected 4-acyl-5-nitroisocoumarins. This procedure was optimized for reaction temperature (150 °C), solvent (nitrobenzene), and Lewis acid (SnCl4). Reaction of 5-nitroisocoumarin with [13C]-carbonyl benzoyl chloride under the optimum conditions gave 5-nitro-3-phenylisocoumarin

  在Friedel-Crafts条件下用芳族酰氯处理5-硝基异香豆素可得到3-芳基-5-硝基异香豆素，而不是预期的4-酰基-5-硝基异香豆素。针对反应温度（150°C），溶剂（硝基苯）和路易斯酸（SnCl 4）优化了该程序。5-硝基异香豆素与[ 13 C]-羰基苯甲酰氯在最佳条件下反应，得到5-硝基-3-苯基异香豆素，其中13 C位于杂环的3-C处，表明苯甲酰基碳骨架被引入完好无损的。
• One-pot tandem Hurtley–retro-Claisen–cyclisation reactions in the synthesis of 3-substituted analogues of 5-aminoisoquinolin-1-one (5-AIQ), a water-soluble inhibitor of PARPs
  作者：Esther C.Y. Woon、Peter T. Sunderland、Helen A. Paine、Matthew D. Lloyd、Andrew S. Thompson、Michael D. Threadgill

  DOI：10.1016/j.bmc.2013.06.031

  日期：2013.9

  Poly(ADP-ribose)polymerase-1 (PARP-1) is an important target for drug design for several therapeutic applications. 5-Aminoisoquinolin-1-one (5-AIQ) is a highly water-soluble lead compound; synthetic routes to 3-substituted analogues were explored. Tandem Hurtley coupling of beta-diketones with 2-bromo-3-nitrobenzoic acid, retro-Claisen acyl cleavage and cyclisation gave the corresponding 3-substituted 5-nitroisocoumarins. Treatment with ammonia at high temperature and reduction with tin(II) chloride gave eleven target 3-substituted 5-AIQs, which were all soluble in water (>1% w/ v) as their HCl salts. Most were more potent than 5-AIQ as inhibitors of PARP-1 and of PARP-2 in vitro, the most active being 5-amino-3-methylisoquinolin-1-one (PARP-1: IC50 = 0.23 mu M vs IC50 = 1.6 mu M for 5-AIQ). Some rationalisation of the SAR was achieved through molecular modelling. (C) 2013 Elsevier Ltd. All rights reserved.
• AMES D. E.; RIBEIRO O., J. CHEM. SOC. PERKIN TRANS., PART 1 <JCPK-BH>, 1976, NO 10, 1073-1078
  作者：AMES D. E.、 RIBEIRO O.

  DOI：——

  日期：——