4-hydroxy-7-ethoxycoumarin | 55004-81-4

• 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-hydroxy-7-ethoxycoumarin
• 英文别名: 7-ethoxy-4-hydroxycoumarin；7-Ethoxy-4-hydroxy-2H-1-benzopyran-2-one；7-ethoxy-4-hydroxychromen-2-one
• CAS: 55004-81-4
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: BPWIJZQVCZRWTJ-UHFFFAOYSA-N

物化性质

• 熔点：
  267-268 °C
• 沸点：
  395.6±42.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

7-乙氧基-4-羟基-2H-1-苯并吡喃-2-酮是7-乙氧香豆素的人类已知代谢物。

2H-1-Benzopyran-2-one, 7-ethoxy-4-hydroxy- is a known human metabolite of 7-ethoxycoumarin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  4-hydroxy-7-ethoxycoumarin 以95%的产率得到
  参考文献：
  名称：

  BUCKLE D. R.; CANTELLO B. C. C.; SMITH H.; SPICER B. A., J. MED, CHEM. , 1975, 18, NO 4, 391-394

  摘要：

  DOI：

文献信息

• Click synthesis of <i>N</i>¹-(<i>β</i>-<scp>D</scp>-<i>ribo</i>furanosyl)-<i>C</i>⁴-(coumarin-4<i>″</i>-yl)-1,2,3-triazoles
  作者：Vipin K. Maikhuri、Kapil Bohra、Smriti Srivastava、Kavita、Ashok K. Prasad

  DOI：10.1080/00397911.2019.1657150

  日期：2019.11.17

  Abstract A series of eight N1-(β-D-ribofuranosyl)-C4-(coumarin-4′′-yl)-1,2,3-triazoles have been synthesized by Cu(I)-catalyzed click reaction of 1-azido-1-deoxy-2,3,5-tri-O-benzoyl-β-D-ribofuranose with differently substituted 4-ethynylcoumarins followed by debenzoylation of the resulted N1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-C4-(coumarin-4″-yl)-1,2,3-triazoles in 71 to 89% overall yields.

  摘要 通过 Cu(I) 催化的 1-叠氮基点击反应合成了一系列 8 个 N1-(β-D-呋喃核糖基)-C4-(香豆素-4''-基)-1,2,3-三唑。 -1-脱氧-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖与不同取代的4-乙炔基香豆素，然后对所得N1-(2',3',5'-tri-O-苯甲酰基-β-D-呋喃核糖基)-C4-(香豆素-4″-基)-1,2,3-三唑，总产率为 71% 至 89%。所有合成化合物的结构均建立在其光谱数据分析的基础上，并通过其中一种模型苯甲酰化化合物的 X 射线数据分析进一步证实，即 N1-(2',3',5'-tri- O-苯甲酰基-β-D-呋喃核糖基)-C4-(7″-异丙氧基香豆素-4″-基)-1,2,3-三唑。图形概要
• Coumarin derivatives for the treatment of allergies
  申请人：Beecham Group Limited

  公开号：US03974289A1

  公开（公告）日：1976-08-10

  Pharmaceutical compositions for the treatment of allergies are produced using coumarin derivatives as the active agent. Certain of these compounds and their salts are novel.

  使用香豆素衍生物作为活性成分，生产用于治疗过敏的制药组合物。其中某些化合物及其盐是新颖的。
• Di Braccio; Roma; Leoncini, Il Farmaco, 1995, vol. 50, # 10, p. 703 - 711
  作者：Di Braccio、Roma、Leoncini、Poggi

  DOI：——

  日期：——
• Shridhar, D. R.; Ram, Bhagat; Sarma, C. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. <B> 22, # 8, p. 835 - 836
  作者：Shridhar, D. R.、Ram, Bhagat、Sarma, C. R.、Sachdeva, Y. P.

  DOI：——

  日期：——
• Microwave-Assisted Synthesis and Antifungal Activities of Polysubstituted Furo[3,2-c]chromen-4-ones and 7,8,9,10-Tetrahydro-6<i>H</i>-benzofuro[3,2-c]chromen-6-ones
  作者：Rongrong Zhang、Zichao Xu、Wenzheng Yin、Pin Liu、Weihua Zhang

  DOI：10.1080/00397911.2014.935436

  日期：2014.11.17

  An efficient and novel microwave-assisted synthesis of furo[3,2-c]chromen-4-ones and 7,8,9,10-tetrahydro-6H-benzofuro[3,2-c]chromen-6-ones via 4-hydroxycoumarins with alpha-chloroketones or alpha-bromocyclohexanone in the presence of acetic acid (AcOH)/ammonium acetate (NH4OAc) using DMF as solvent under microwave irradiation is described. Systematically, antifungal biological tests showed that most of the compounds exhibited potent antifungal activity against Botrytis cinerea, Collecterichum capsica, Alternaria solani, Gibberella zeae, and Rhizoctorzia solani at the concentration of 50 mu g/mL. The corresponding EC50 values of these analogues have been detected, and compound 4i showed better antifungal activity against tested fungi Botrytis cinerea and Collecterichum capsica than the reference Osthol.