5H-chromeno[4,3-b]pyridin-5-one | 85175-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5H-chromeno[4,3-b]pyridin-5-one
• 英文别名: 5H-(1)Benzopyrano(4,3-b)pyridin-5-one；chromeno[4,3-b]pyridin-5-one
• CAS: 85175-31-1
• 化学式: C₁₂H₇NO₂
• 分子量: 197.193
• InChiKey: GNWLMVUQBPYECO-UHFFFAOYSA-N

物化性质

• 熔点：
  169 °C(Solv: methanol (67-56-1))
• 沸点：
  386.5±11.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5H-chromeno[4,3-b]pyridin-5-one 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 甲基叔丁基醚 为溶剂， 生成 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chromeno[4,3-b]pyridin-5-one
  参考文献：
  名称：

  US2022/289778

  摘要：

  公开号：
• 作为产物：
  描述：

  methyl 2-(2-chlorophenyl)nicotinate 在 噻吩-2-甲酸亚铜(I) 、 四甲基乙二胺 、 caesium carbonate 作用下， 以 水 为溶剂， 300.0 ℃ 、1.72 MPa 条件下， 反应 0.17h， 以62%的产率得到5H-chromeno[4,3-b]pyridin-5-one
  参考文献：
  名称：

  Cu(I)-mediated lactone formation in subcritical water: a benign synthesis of benzopyranones and urolithins A–C

  摘要：

  Benzopyranones were successfully synthesized using Cu(I)-mediated C-O bond formation in subcritical water. A number of benzopyranone derivatives including polymethoxy benzopyranones, benzopyranopyridones, cbromenoindolones, and furochromenones were synthesized in satisfactory yield. This methodology was further applied to synthesize the intestinal microbial metabolites, urolithins A, B, and C, which were found to exhibit potent antioxidant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.045

文献信息

• Electrochemical C−O Bond Formation: Facile Access to Aromatic Lactones
  作者：Xiang-Zhang Tao、Jian-Jun Dai、Jie Zhou、Jun Xu、Hua-Jian Xu

  DOI：10.1002/chem.201801108

  日期：2018.5.11

  An efficient and robust methodology based on electrochemical techniques for the direct synthesis of aromatic lactones through dehydrogenative C−O cyclization is described. This new and useful electrochemical reaction can tolerate a variety of functional groups, and is scalable to 100 g under mild conditions. Remarkably, heterocycle‐containing substrates can be employed, thus expanding the scope of

  描述了一种基于电化学技术的有效且稳健的方法，用于通过脱氢C-O环化反应直接合成芳族内酯。这种新的有用的电化学反应可以耐受各种官能团，在温和条件下可扩展至100 g。值得注意的是，可以使用含杂环的底物，从而扩大了自由基C-O环化反应的范围。
• Novel and Efficient One-Step Parallel Synthesis of Dibenzopyranones via Suzuki−Miyaura Cross Coupling
  作者：Kodumuru Vishnumurthy、Alexandros Makriyannis

  DOI：10.1021/cc100068a

  日期：2010.9.13

  Microwave-promoted novel and efficient one-step parallel synthesis of dibenzopyranones and heterocyclic analogues from bromo arylcarboxylates and o-hydroxyarylboronic acids via Suzuki−Miyaura cross coupling reaction is described. Spontaneous lactonization gave dibenzopyranones and heterocyclic analogues bearing electron-donating and -withdrawing groups on both aromatic rings in good to excellent yields

  描述了通过微波促进的新型有效的一步苯并吡喃酮和杂环类似物通过Suzuki-Miyaura交叉偶联反应从溴代芳基羧酸盐和邻-羟基芳基硼酸平行合成的方法。自发的内酯化以良好或优异的产率得到了在两个芳族环上带有给电子和吸电子基团的二苯并吡喃酮和杂环类似物。
• Efficient Synthesis of Pyrido[3,2-c]coumarins via Silver Nitrate Catalyzed Cycloisomerization and Application to the First Synthesis of Polyneomarline C
  作者：Jeong A Yoon、Young Taek Han

  DOI：10.1055/s-0037-1610730

  日期：2019.12

  Herein, we report an efficient method for the synthesis of the pyrido[3,2-c]coumarin scaffold, one of the privileged heterocycle-fused coumarin scaffolds, via a AgNO3-catalyzed cycloisomerization of 4-(propynylamino)coumarins obtained from diverse 4-hydroxycoumarins. This concise method affords pyrido[3,2-c]coumarin analogues bearing diverse substituents on the benzene or pyridine ring in moderate

  在本文中，我们报告了一种通过AgNO 3催化的4-（丙炔基氨基）香豆素的环异构化合成吡啶并[3,2- c ]香豆素骨架的一种有效方法，该吡啶并[3,2- c ]香豆素骨架是一种特权杂环融合的香豆素骨架。4-羟基香豆素。这种简洁的方法以中等到良好的产率提供了在苯或吡啶环上带有各种取代基的吡啶并[3,2- c ]香豆素类似物。此外，该方法还扩展到了三步分离法的简便合成，该方法是从中草药Polyalthia nemoralis A. DC。分离出的天然吡啶并[3,2- c ]香豆素衍生物。已知的4-羟基香豆素。
• [EN] INHIBITORS OF D-AMINO ACID OXIDASE<br/>[FR] INHIBITEURS D'ACIDE AMINÉ D OXYDASE
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2014025993A1

  公开（公告）日：2014-02-13

  D-amino acid oxidase (DAAO) inhibitors and methods of their use, either alone or in combination with D-serine or D-alanine, to facilitate allosteric activation of NMDA receptor-mediated neurotransmission and methods of their use as therapeutic agents for treating a subject afflicted with one or more cognitive-disorders, such as schizophrenia, including subjects suffering from negative symptoms and cognitive impairments, post-traumatic stress disorder (PTSD), or pain, are disclosed.

  抑制D-氨基酸氧化酶（DAAO）及其使用方法，可以单独使用或与D-丝氨酸或D-丙氨酸结合，以促进NMDA受体介导的神经递质的变构激活，并作为治疗剂用于治疗患有一个或多个认知障碍的受试者，如精神分裂症，包括患有消极症状和认知障碍的受试者，创伤后应激障碍（PTSD）或疼痛等。
• INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20150218156A1

  公开（公告）日：2015-08-06

  D-amino acid oxidase (DAAO) inhibitors and methods of their use, either alone or in combination with D-serine or D-alanine, to facilitate allosteric activation of NMDA receptor-mediated neurotransmission and methods of their use as therapeutic agents for treating a subject afflicted with one or more cognitive-disorders, such as schizophrenia, including subjects suffering from negative symptoms and cognitive impairments, post-traumatic stress disorder (PTSD), or pain, are disclosed.

  本文介绍了D-氨基酸氧化酶（DAAO）抑制剂及其使用方法，无论是单独使用还是与D-丝氨酸或D-丙氨酸结合使用，以促进NMDA受体介导的神经递质的异构激活，并作为治疗剂治疗患有一种或多种认知障碍的受试者，例如精神分裂症，包括患有消极症状和认知障碍的受试者，创伤后应激障碍（PTSD）或疼痛。