4,5-dihydroxycoumarin | 30992-74-6

• 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: 4,5-dihydroxycoumarin
• 英文别名: 4,5-Dihydroxy-cumarin；4,5-Dihydroxy-2H-1-benzopyran-2-one；4,5-dihydroxychromen-2-one
• CAS: 30992-74-6
• 化学式: C₉H₆O₄
• 分子量: 178.144
• InChiKey: SSCSOYWLYNIXMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  4,5-dihydroxycoumarin 在 氢氧化钾 作用下， 生成 2,6-二羟基苯乙酮
  参考文献：
  名称：

  Synthesen von Heterocyclen, 20. Mitt.: Eine Synthese von Di-und Trihydroxycumarinen

  摘要：

  DOI：

  10.1007/bf00925236
• 作为产物：
  描述：

  3-Benzyl-4,5-dihydroxy-cumarin 在 三氯化铝 作用下， 生成 4,5-dihydroxycoumarin
  参考文献：
  名称：

  Synthesen von Heterocyclen, 20. Mitt.: Eine Synthese von Di-und Trihydroxycumarinen

  摘要：

  DOI：

  10.1007/bf00925236

文献信息

• [EN] SUBSTITUTED FUROCHROMENE COMPOUNDS OF ANTIINFLAMMATORY ACTION<br/>[FR] COMPOSES DE FUROCHROMENE SUBSTITUES A ACTION ANTI-INFLAMMATOIRE
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005010006A1

  公开（公告）日：2005-02-03

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diseases and/or conditions in humans.

  本发明涉及公式（I）的新化合物，包括所有立体异构体和互变异构体，以及其药用可接受盐和溶剂合物，用于预防和治疗人类的哮喘和其他炎症性疾病和/或情况的过程和反应中间体，以及它们的使用。
• [EN] SUBSTITUTED FUROCHROMENES, PREPARATION THEREOF AND THEIR ANTIINFLAMMATORY ACTION<br/>[FR] FUROCHROMENES SUBSTITUES, PREPARATION DE CEUX-CI ET LEUR ACTION ANTI-INFLAMMATOIRE
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005010007A1

  公开（公告）日：2005-02-03

  The invention relates to novel compounds of formula (I) including all their tautomers to pharmaceutically acceptable salts and solvates thereof, to processes and reactive intermediates for the preparation thereof; to processes and reactive intermediates for the preparation of compounds of formula (II) including all their stereoisomers and tautomers to the use of the compounds of the formula (II) as suitable precursors for the preparation of the compounds of the formula (I) as well as to use of the compounds of the formula (I) and of the compounds of the formula (II) as therapeutically active agents in the prophylaxis and treatment of asthma and other inflammatory diesases and conditions in humans.

  该发明涉及公式（I）的新化合物，包括所有其互变异构体，以及其药学上可接受的盐和溶剂化合物；用于其制备的过程和活性中间体；用于制备公式（II）化合物的过程和活性中间体，包括其所有立体异构体和互变异构体；将公式（II）化合物用作公式（I）化合物的适当前体的用途，以及将公式（I）化合物和公式（II）化合物用作在人类预防和治疗哮喘和其他炎症性疾病和症状中的治疗活性剂的用途。
• Substituted furochromenes, preparation thereof and their antiinflammatory action
  申请人：Mercep Mladen

  公开号：US20060148889A1

  公开（公告）日：2006-07-06

  The invention relates to novel compounds of the formula (I) including all their tautomers, to pharmaceutically acceptable salts and solvates thereof, to processes and reactive intermediates for the preparation thereof, and to processes and reactive intermediates for the preparation of the compounds of the formula (II) including all their stereoisomers and tautomers to the use of the compounds of the formula (II) as suitable precursors for the preparation of the compounds of the formula (I) as well as to use of the compounds of the formula (I) and of the compounds of the formula (II) as therapeutically active agents in the prophylaxis and treatment of asthma and other inflammatory diesases and conditions in humans.

  本发明涉及公式（I）的新化合物及其所有互变异构体，其药学上可接受的盐和溶剂化物，以及其制备的过程和反应中间体，以及公式（II）的化合物及其所有立体异构体和互变异构体的制备过程和反应中间体。本发明还涉及使用公式（II）的化合物作为制备公式（I）的合适前体，以及使用公式（I）和公式（II）的化合物作为治疗哮喘和其他人类炎症疾病和病况的治疗活性剂的用途。
• Substituted furochromene compounds of antiinflammatory action
  申请人：Mercep Mladen

  公开号：US20060148890A1

  公开（公告）日：2006-07-06

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers thereof, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diesases and/or conditions in humans.

  本发明涉及式（I）的新化合物，包括其所有立体异构体和互变异构体、药学上可接受的盐和溶剂合物，以及其制备过程和反应中间体，以及它们在预防和治疗人类哮喘和其他炎症性疾病和/或病况中的用途。
• Keto–enol tautomerism, NMR spectra, and H–D exchange of 4-hydroxycoumarins
  作者：Valery F. Traven、Vadim V. Negrebetsky、Larisa I. Vorobjeva、Edward Andrew Carberry

  DOI：10.1139/v97-043

  日期：1997.4.1

  4-Hydroxycoumarin 1, 4,5-dihydroxycoumarin 2, and 4,7-dihydroxycoumarin 3 undergo H–D exchange at the C(3) atom of the lactone ring. Although only the 4-hydroxy-2-chromenone tautomeric forms are seen in the ¹H and ¹³C NMR spectra of compounds 1–3, the equilibrium between the 4-hydroxy-2-chromenone and 2,4-chromandione forms is suggested to be the key step in the H–D exchange reaction. 4,5-Dihydroxycoumarin shows the highest rate of the reaction, since H-bonding between 5-hydroxyl and 4-keto functional groups can provide relative stability to the 5-hydroxy-2,4-chromandione tautomeric form, a probable intermediate of the exchange. NMR spectra and tautomeric transformations of 3-(4-methoxyphenylazo)-4-hydroxycoumarin 4 and 3-acetyl-4-hydroxycoumarin 5 are also discussed. The stabilities of different tautomeric forms of compounds 1–5 have been evaluated by MNDO calculations. Keywords: 4-hydroxycoumarin derivatives, keto-enol tautomerism, H–D-exchange.

  4-羟基香豆素1，4,5-二羟基香豆素2和4,7-二羟基香豆素3在内酰环的C（3）原子处发生H-D交换。尽管化合物1-3的1H和13C NMR光谱中只能看到4-羟基-2-香豆酮互变异构体形式，但4-羟基-2-香豆酮和2,4-香酮二酮形式之间的平衡被认为是H-D交换反应的关键步骤。4,5-二羟基香豆素显示出最高的反应速率，因为5-羟基和4-酮官能团之间的氢键可以为5-羟基-2,4-香酮二酮互变异构体形式提供相对稳定性，这是交换的可能中间体。还讨论了3-（4-甲氧基苯偶氮）-4-羟基香豆素4和3-乙酰基-4-羟基香豆素5的NMR光谱和互变异构体转化。通过MNDO计算评估了化合物1-5的不同互变异构体形式的稳定性。关键词：4-羟基香豆素衍生物，酮-烯醇互变异构，H-D交换。