ethyl 8-methyl-4-oxo-4H-chromene-2-carboxylate | 33543-99-6

• 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: ethyl 8-methyl-4-oxo-4H-chromene-2-carboxylate
• 英文别名: ethyl 8-methyl-4-oxochromene-2-carboxylate
• CAS: 33543-99-6
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: HTBQNHVXXPOWAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 8-methyl-4-oxo-4H-chromene-2-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 水 、 过氧化苯甲酰 作用下， 以 氯苯 、 丙酮 为溶剂， 反应 21.25h， 生成 ethyl 8-(hydroxymethyl)-4-oxo-4H-chromene-2-carboxylate
  参考文献：
  名称：

  [EN] ANTI-INFECTIVE AGENTS
  [FR] AGENTS ANTI-INFECTIEUX

  摘要：

  本发明涉及一类新型的基于色酮-2-羧酰胺化合物的抑制剂，其通式为(I)，其中R1、R2、R3、R4、R5、R6、R7、R8和X如本文所定义，其在医学上的用途，特别是作为抗感染剂的用途，包括含有它们的组合物，其制备过程以及用于这些过程的中间体。

  公开号：

  WO2017221002A1
• 作为产物：
  描述：

  diethyl 2-(2-methylphenoxy)but-2-enedioate 在 polyphosphoric acid 作用下， 以 neat (no solvent) 为溶剂， 生成 ethyl 8-methyl-4-oxo-4H-chromene-2-carboxylate
  参考文献：
  名称：

  An Efficient Construction of 4-Oxo-4H-chromene-2-carboxylate Derivatives via One-Pot Cascade Reaction Under Solvent-Free Conditions

  摘要：

  An efficient synthetic strategy to chromone derivatives from commercially available diethyl acetylenedicarboxylate and phenols via a one-pot cascade reaction has been developed. Performing the reaction using pyridine and polyphosphoric acid as the catalyst at room temperature and 90 degrees C without any solvent gave the chromone derivatives in good to high yields at one time. A possible reaction pathway was also proposed and supported by the experiment. This protocol is environmentally friendly and metal-free, with advantages including short reaction times, convenient operation, and mild reaction conditions.

  DOI：

  10.3987/com-15-13191

文献信息

• Quinolinyl-chromone derivatives and use for treatment of hypersensitive
  申请人：Rorer Pharmaceutical Corporation

  公开号：US04977162A1

  公开（公告）日：1990-12-11

  This invention relates to certain quinolinyl-chromone compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties.

  这项发明涉及某些喹啉基-香豆素化合物及其作为有价值的药用剂的用途，特别是作为脂氧酶抑制剂和/或白三烯拮抗剂，具有抗炎和抗过敏性能。
• Quinolinyl-benzopyran derivatives as antagonists of leukotriene D4
  申请人：——

  公开号：US05082849A1

  公开（公告）日：1992-01-21

  This invention relates to certain quinolinyl-benzopyran compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists and/or mediator release inhibitors possessing anti-inflammatory and anti-allergic properties.

  这项发明涉及某些喹啉基-苯并吡喁化合物及其作为有价值的药物代理的用途，特别是作为脂氧合酶抑制剂和/或白三烯拮抗剂和/或介质释放抑制剂，具有抗炎和抗过敏特性。
• Therapeutic Heterocyclic Compounds 507
  申请人：Pierson Edward

  公开号：US20080076759A1

  公开（公告）日：2008-03-27

  Provided herein is a compound having the formula (I): Wherein said compounds are useful for the treatment of psychiatric disorders including but not limited to depression, generalized anxiety, eating disorders, dementia, panic disorder, and sleep disorders. The compounds may also be useful in the treatment of gastrointestinal disorders, cardiovascular regulation, motor disorders, endocrine disorders, vasospasm and sexual dysfunction. The compounds are 5 HT 1B and 5 HT 1D antagonists.

  本文提供的化合物具有以下公式（I）：其中这些化合物可用于治疗精神障碍，包括但不限于抑郁症、广泛性焦虑症、进食障碍、痴呆症、恐慌症和睡眠障碍。这些化合物也可能有助于治疗胃肠障碍、心血管调节、运动障碍、内分泌障碍、血管痉挛和性功能障碍。这些化合物是5HT1B和5HT1D受体拮抗剂。
• Process of producing 2-cyano-4-oxo-4H-benzopyran compounds
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0634409A1

  公开（公告）日：1995-01-18

  There is disclosed a process of producing a 2-cyano-4-oxo-4H-benzopyran compound of the general formula (2): wherein R¹ and R² are independently hydrogen, halogen, hydroxy, C₁-C₅ alkyl, C₁-C₅ alkoxy, nitro or a group of the RCONH wherein R is C₁-C₂₀ alkyl, phenyl, phenyl-substituted (C₁-C₂₀)alkyl, phenyl(C₁-C₂₀)alkoxyphenyl or (C₁-C₂₀)alkoxyphenyl. This production process is characterized in that a carboxamide of the general formula (1): wherein R¹ and R² are each as defined above, is reacted with a dehydrating agent in the presence of a pyridine compound of the general formula (4): wherein A¹ and A² are independently hydrogen or C₁-C₅ alkyl. If the final product cannot be obtained as crystals having good filtration properties by ordinary treatments, a novel technique as disclosed herein can provide such crystals by dissolving the reaction product in an organic solvent insoluble or slightly soluble in water; pouring the resultant solution into water; and removing the organic solvent by distillation with stirring to effect the crystallization of the final product.

  本发明公开了一种通式（2）的 2-氰基-4-氧代-4H-苯并吡喃化合物的生产工艺： 其中 R¹ 和 R² 独立地为氢、卤素、羟基、C₁-C₅ 烷基、C₁-C₅ 烷氧基、硝基或 RCONH 的基团，其中 R 为 C₁-C₂₀ 烷基、苯基、苯基取代(C₁-C₂₀)烷基、苯基(C₁-C₂₀)烷氧基苯基或(C₁-C₂₀)烷氧基苯基。该生产工艺的特征在于通式(1)的羧酰胺： 其中 R¹ 和 R² 均如上定义，在通式（4）的吡啶化合物存在下与脱水剂反应： 其中 A¹ 和 A² 独立地为氢或 C₁-C₅ 烷基。如果通过普通的处理方法无法获得具有良好过滤性能的结晶体，那么本文公开的一种新技术可以提供这种结晶体，其方法是将反应产物溶解在不溶于水或微溶于水的有机溶剂中；将所得溶液倒入水中；然后在搅拌下通过蒸馏除去有机溶剂，以实现最终产物的结晶。
• EP0434827A4
  申请人：——

  公开号：EP0434827A4

  公开（公告）日：1992-01-08