coumarin-7-yl (9Z,12R)-12-hydroxyoctadec-9-enoate | 1225446-73-0

• 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: coumarin-7-yl (9Z,12R)-12-hydroxyoctadec-9-enoate
• 英文别名: (2-oxochromen-7-yl) (Z,12R)-12-hydroxyoctadec-9-enoate
• CAS: 1225446-73-0
• 化学式: C₂₇H₃₈O₅
• 分子量: 442.596
• InChiKey: XQCPQOOQAGZOLP-UQBDUDKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-羟基香豆素 、 蓖麻油酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到coumarin-7-yl (9Z,12R)-12-hydroxyoctadec-9-enoate
  参考文献：
  名称：

  7-Hydroxy-coumarin derivatives: synthesis, characterization and preliminary antimicrobial activities

  摘要：

  A new series of 7-O-coumarinyl alkenoates were synthesized from 7-hydroxyl-coumarin and fatty acids using DCC and DMAP as catalyst. The synthesized compounds were characterized on the basis of their spectral data. All the target compounds were evaluated for their in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Streptococcus pyogene, Pseudomonas aeruginosa, Salmonella typhimurium, Escherichia coli and fungal cultures of Candida albicans, Candida krusei, Candida parapsilosis and Cryptococcus neoformans. The minimum inhibitory concentration (MIC) was determined for the test compounds as well as for reference standards. Among the tested compounds, 7-O-coumarinyl (9Z, 12R)-12-hydroxyoctadec-9-enoate and 7-O-coumarinyl (12Z, 9R)-9-hydroxyoctadec-12-enoate showed the most potent antifungal as well as antibacterial activities.

  DOI：

  10.1007/s00044-010-9347-9

文献信息

• 7-Hydroxy-coumarin derivatives: synthesis, characterization and preliminary antimicrobial activities
  作者：Nida N. Farshori、Mudasir R. Banday、Anis Ahmad、Asad U. Khan、Abdul Rauf

  DOI：10.1007/s00044-010-9347-9

  日期：2011.6

  A new series of 7-O-coumarinyl alkenoates were synthesized from 7-hydroxyl-coumarin and fatty acids using DCC and DMAP as catalyst. The synthesized compounds were characterized on the basis of their spectral data. All the target compounds were evaluated for their in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Streptococcus pyogene, Pseudomonas aeruginosa, Salmonella typhimurium, Escherichia coli and fungal cultures of Candida albicans, Candida krusei, Candida parapsilosis and Cryptococcus neoformans. The minimum inhibitory concentration (MIC) was determined for the test compounds as well as for reference standards. Among the tested compounds, 7-O-coumarinyl (9Z, 12R)-12-hydroxyoctadec-9-enoate and 7-O-coumarinyl (12Z, 9R)-9-hydroxyoctadec-12-enoate showed the most potent antifungal as well as antibacterial activities.