2-oxo-2H-chromene-8-carbaldehyde | 212515-90-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-oxo-2H-chromene-8-carbaldehyde
• 英文别名: 8-formyl-2H-chromen-2-one；coumarin-8-aldehyde；8-formylcoumarin；8-Formyl coumarin；2-oxochromene-8-carbaldehyde
• CAS: 212515-90-7
• 化学式: C₁₀H₆O₃
• 分子量: 174.156
• InChiKey: FMGJBLRERFZGCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-oxo-2H-chromene-8-carbaldehyde 在 吡啶 、 氨 、 pyridinium hydrobromide perbromide 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 31.83h， 生成
  参考文献：
  名称：

  Coumarin 1,4-Dihydropyridine Derivatives

  摘要：

  A series of 1,4-dihydropyridines bearing a coumarin moiety in 4-position was synthesized. The compounds were evaluated for inotropic, chronotropic and calcium antagonist activities. The replacement of the o-nitrophenyl moiety of nifedipine with a coumarin or phenylcoumarin system is accompained by a decrease of the activity on myocardial and vascular parameters, but the synthesized compounds showed selective inhibiting effects on cardiac contractility and frequency. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00037-6
• 作为产物：
  描述：

  8-methylcoumarin 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 乌洛托品 作用下， 以 四氯化碳 为溶剂， 反应 8.25h， 生成 2-oxo-2H-chromene-8-carbaldehyde
  参考文献：
  名称：

  Coumarin 1,4-Dihydropyridine Derivatives

  摘要：

  A series of 1,4-dihydropyridines bearing a coumarin moiety in 4-position was synthesized. The compounds were evaluated for inotropic, chronotropic and calcium antagonist activities. The replacement of the o-nitrophenyl moiety of nifedipine with a coumarin or phenylcoumarin system is accompained by a decrease of the activity on myocardial and vascular parameters, but the synthesized compounds showed selective inhibiting effects on cardiac contractility and frequency. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00037-6

文献信息

• BX3-Mediated Intermolecular Formation of Functionalized 3-Halo-1H-indenes via Cascade Halo-Nazarov-Type Cyclization
  作者：Rodney A. Fernandes、Anupama Kumari

  DOI：10.1055/s-0039-1690881

  日期：2020.8

  inexpensive reagents and a convenient and mild reaction procedure to generate halo-functionalized indenes (45 examples). The reaction was also extended to 8-formylcoumarins to deliver coumarin-based 3-halo-1H-indenes in 79–95% yield (6 examples). The reaction involves conversion of the aldehyde into an sp3 carbon with two new C–C bonds and additionally a C–X bond is formed (X = halide).

  已经开发了由BX 3促进的由4-氧代-4 H-亚甲基苯甲醛和炔烃3-卤代官能化的1 H-茚的分子间区域选择性合成。BX 3表现出路易斯酸催化剂和卤化物源的双重作用，可用于卤代-Nazarov型环化反应。整个转化过程代表了一种有效的级联环状反应，它采用了容易获得的起始原料，廉价的试剂以及便捷而温和的反应程序来生成卤官能化的茚满（45个例子）。该反应还扩展到8-甲酰基香豆素，以提供基于香豆素的3-卤代-1 H-茚的产率为79–95％（6个示例）。该反应涉及通过两个新的C–C键将醛转化为sp 3碳，并另外形成C–X键（X =卤化物）。
• Coumarin derivatives useful as tnf alpha inhibitors
  申请人：Cheng Fei Jie

  公开号：US20050014705A1

  公开（公告）日：2005-01-20

  Novel compounds composition capable of inhibiting TNFα and having antiimmunoinflammatory and autoimmune properties useful in a pharmaceutical composition, such as for a drug containing this as an active ingredient; and a therapeutic method with the use of these novel compounds.

  一种新型化合物组合，能够抑制TNFα，具有抗免疫炎症和自身免疫性质，在制药组合物中有用，例如作为含有此化合物作为活性成分的药物；以及使用这些新型化合物的治疗方法。
• Coumarin derivatives useful as TNFalpha inhibitors
  申请人：Cheng Fei Jie

  公开号：US20060020138A1

  公开（公告）日：2006-01-26

  Novel compounds composition capable of inhibiting TNFα and having anti immunoinflammatory and autoimmune properties useful in a pharmaceutical composition, such as for a drug containing this as an active ingredient; and a therapeutic method with the use of these novel compounds.

  一种能够抑制TNFα并具有抗免疫炎症和自身免疫特性的新型化合物组合，适用于制备药物组合物，例如含有该化合物作为活性成分的药物；以及使用这些新型化合物的治疗方法。
• COUMARIN DERIVATIVES USEFUL AS TNF ALPHA INHIBITORS
  申请人：Cheng Jie Fei

  公开号：US20100197917A1

  公开（公告）日：2010-08-05

  Novel compounds composition capable of inhibiting TNFα and having antiimmunionflammatory and autoimmune properties useful in a pharmaceutical composition, such as for a drug containing this as an active ingredient; and a therapeutic method with the use of these novel compounds.

  一种能够抑制TNFα并具有抗免疫炎症和自身免疫性质的新型化合物组合，可用于制备药物组合物，例如包含该化合物作为活性成分的药物；以及使用这些新型化合物的治疗方法。
• Coumarin derivatives useful as TNFα inhibitors
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US07872142B2

  公开（公告）日：2011-01-18

  Novel compounds composition capable of inhibiting TNFα and having antiimmunoinflammatory and autoimmune properties useful in a pharmaceutical composition, such as for a drug containing this as an active ingredient; and a therapeutic method with the use of these novel compounds.

  新型化合物组成，能够抑制TNFα，并具有抗免疫炎症和自身免疫特性，适用于制药组合物，如含有此化合物作为活性成分的药物；以及使用这些新型化合物的治疗方法。