8-氯-2H-1,4-苯并恶嗪-3(4H)-酮 | 57245-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 8-氯-2H-1,4-苯并恶嗪-3(4H)-酮
• 中文别名: 8-氯-2H-苯并[B][1,4]噁嗪-3(4H)-酮
• 英文名称: 8-chloro-3,4-dihydro-2H-1,4-benzoxazin-3-one
• 英文别名: 8-chloro-2Hbenzo[b][1,4]oxazin-3(4H)-one；8-chloro-4H-benzo[1,4]oxazin-3-one；8-chloro-4H-2,3-dihydro-1,4-benzoxazin-3-one；8-Chloro-2H-benzo[B][1,4]oxazin-3(4H)-one；8-chloro-4H-1,4-benzoxazin-3-one
• CAS: 57245-31-5
• 化学式: C₈H₆ClNO₂
• mdl: MFCD08111618
• 分子量: 183.594
• InChiKey: MRMNWSPHQCJZBC-UHFFFAOYSA-N

物化性质

• 沸点：
  362.7±42.0 °C(Predicted)
• 密度：
  1.393±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-氯-2H-1,4-苯并恶嗪-3(4H)-酮 在 三乙胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.25h， 生成 4-Chloro-6H-5-oxa-7,12a-diaza-benzo[a]anthracen-12-one
  参考文献：
  名称：

  Sastry, C. V. Reddy; Srinivasa Rao, K.; Krishnan, V. S. H., Synthesis, 1988, # 4, p. 336 - 337

  摘要：

  DOI：
• 作为产物：
  描述：

  二氯-苯酚 、 氯乙酰胺 在 caesium carbonate 作用下， 以89%的产率得到8-氯-2H-1,4-苯并恶嗪-3(4H)-酮
  参考文献：
  名称：

  Microwave-assisted Synthesis of Benzo-[1,4]-oxazinones Using MeO-PEG-OMe as Solvent

  摘要：

  以微波加热法和 MeO-PEG-OMe 为溶剂，开发了一种高效的苯并-[1,4]-恶嗪酮的单锅合成方法，并利用所开发的合成方法以良好的产率合成了 8 个苯并-[1,4]-恶嗪酮化合物和 1H 吡啶并[2,3-b][1,4]-恶嗪-2-(3H)-酮。 介绍了通过斯迈尔斯重排法在微波辅助下高效合成各种苯并-[1,4]-恶嗪酮的方法。以 MeO-PEG-OMe (2,000) 为溶剂，处理 2-氯乙酰胺、取代的 2-氯苯酚和碳酸铯，可得到相应的苯并[1,4]-恶嗪酮和 1H-吡啶并[2,3-b][1,4]-恶嗪-2-(3H)-酮，收率中等。

  DOI：

  10.5012/jkcs.2012.56.4.468

文献信息

• Discovery of a lead series of potent benzodiazepine 5-HT2C receptor agonists with high selectivity in functional and binding assays
  作者：Albert Ren、Xiuwen Zhu、Konrad Feichtinger、Juerg Lehman、Michelle Kasem、Thomas O. Schrader、Amy Wong、Huong Dang、Minh Le、John Frazer、David J. Unett、Andrew J. Grottick、Kevin T. Whelan、Michael E. Morgan、Carleton R. Sage、Graeme Semple

  DOI：10.1016/j.bmcl.2019.126929

  日期：2020.3

  potential new 5-HT2 receptor scaffolds based on a simplification of the clinically studied, 5-HT2CR agonist vabicaserin, were designed. An in vivo feeding assay early in our screening process played an instrumental part in the lead identification process, leading us to focus on a 6,5,7-tricyclic scaffold. A subsequent early SAR investigation provided potent agonists of the 5-HT2C receptor that were highly

  根据简化的临床研究，设计了一系列潜在的新型5-HT2受体支架5-HT2CR激动剂vabicaserin。在筛选过程的早期，体内喂养试验在铅识别过程中发挥了重要作用，使我们专注于6,5,7-三环支架。随后的早期SAR研究提供了有效的5-HT2C受体激动剂，该激动剂在功能和结合测定中具有高度选择性，具有良好的大鼠PK特性，并显着降低了大鼠的急性食物摄入量。
• [EN] FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY<br/>[FR] DÉRIVÉS D'IMIDAZOLE ET DE PYRAZOLE CONDENSÉS COMME MODULATEURS DE L'ACTIVITÉ DU TNF
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2015086506A1

  公开（公告）日：2015-06-18

  A series of substituted benzimidazole, imidazo[1,2-a]pyridine and pyrazolo[1,5-a]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

  一系列替代苯并咪唑、咪唑并[1,2-a]吡啶和吡唑并[1,5-a]吡啶衍生物及其类似物，作为强效的人类TNFα活性调节剂，因此在治疗和/或预防各种人类疾病方面具有益处，包括自身免疫和炎症性疾病；神经和神经退行性疾病；疼痛和伤害感知性疾病；心血管疾病；代谢性疾病；眼科疾病；以及肿瘤学疾病。
• Morpholine derivatives
  申请人：Imperial Chemical Industries Limited

  公开号：US03989699A1

  公开（公告）日：1976-11-02

  The disclosure relates to new morpholine derivatives which possess antidepressant activity, to processes for the manufacture of said derivatives and to pharmaceutical compositions containing them. Typical of the morpholine derivatives disclosed is 2-(4H-2,3-dihydro-1,4-benzoxazin-3-one-4-ylmethyl)morpholine.

  本公开涉及具有抗抑郁活性的新型吗啉衍生物，以及制造这些衍生物的过程和包含它们的药物组合物。所披露的吗啉衍生物的典型代表是2-（4H-2,3-二氢-1,4-苯并噁嗪-3-酮-4-基甲基）吗啉。
• PHYTOTOXIC HALOGENATED DERIVATIVES OF BENZOXAZINONES
  申请人：Universidad de Cadiz

  公开号：EP2048136A1

  公开（公告）日：2009-04-15

  The invention relates to phytotoxic halogenated derivatives of benzoxazinones. The aim of the invention relates to the production of novel phytosanitary products that are suitable for agricultural weed control, based on natural chemical substances. The invention comprises novel chemical compounds having high levels of phytotoxic activity and the preparation methods thereof. Said substances are derived from natural products with the 1,4-benzoxazin-3-one skeleton involved in different chemical defense interactions in plants. The inventive compounds have suitable phytotoxic activity levels for use in weed control and for use as stable models for the development of novel phytosanitary products based on the 1,4-benzoxazin-3-one skeleton.

  本发明涉及苯并噁嗪酮的植物毒性卤代衍生物。本发明的目的是以天然化学物质为基础，生产适用于农业除草的新型植物检疫产品。本发明包括具有高水平植物毒性活性的新型化合物及其制备方法。所述物质来源于天然产品，其 1,4-苯并恶嗪-3-酮骨架参与植物不同的化学防御相互作用。本发明的化合物具有合适的植物毒性活性水平，可用于杂草控制，并可用作开发基于 1,4-苯并恶嗪-3-酮骨架的新型植物检疫产品的稳定模型。
• Discovery of non-glucoside SGLT2 inhibitors
  作者：An-Rong Li、Jian Zhang、Joanne Greenberg、TaeWeon Lee、Jiwen Liu

  DOI：10.1016/j.bmcl.2011.02.056

  日期：2011.4

  A series of benzothiazinone and benzooxazinone derivatives were discovered as SGLT2 inhibitors. The optimization led to the discovery of compounds 31 and 32, which exhibited similar potency and better SGLT1 selectivity compared to dapagliflozin. These compounds may provide novel promising scaffolds, which are different from phlorizin-based SGLT2 inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.