(E)-3-(3-oxo-1-butenyl)-1H-2-benzopyran-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: (E)-3-(3-oxo-1-butenyl)-1H-2-benzopyran-1-one
• 英文别名: 3-((E)-3-oxobut-1-enyl)-1H-isochromen-1-one；(E)-3'-oxoartemidin；3-[(E)-3-oxobut-1-enyl]isochromen-1-one
• 化学式: C₁₃H₁₀O₃
• 分子量: 214.221
• InChiKey: IATQFIVMNWTIGE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丁烯酮 、 3-Brom-isocumarin 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以60%的产率得到(E)-3-(3-oxo-1-butenyl)-1H-2-benzopyran-1-one
  参考文献：
  名称：

  Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies

  摘要：

  A series of novel 3-substituted isocoumarins was prepared via Pd-catalysed coupling processes and screened in vitro for antifungal activity against Candida species. The study revealed antifungal potential of isocoumarins possessing the azole substituents, which, in some cases, showed biological properties equal to those of clinically used voriconazole. Selected compounds were also screened against voriconazole resistant Candida krusei 6258 and a clinical isolate Candida parapsilosis CA-27. Although the activity against these targets needs to be improved further, the results emphasise additional potential of this new class of antifungal compounds. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.086

文献信息

• Synthesis of Side Chain Substituted 3-Butylisocoumarins and Absolute Configurations of Natural Isocoumarins from Artemisia dracunculus
  作者：Gerda Lutz-Kutschera、Doris Engelmeier、Franz Hadacek、Andreas Werner、Harald Greger、Otmar Hofer

  DOI：10.1007/s00706-003-0046-6

  日期：2003.9.1

  A series of 3-hydroxy- and 3-bromobutyl-substituted isocoumarins was synthesized. The absolute configurations of three isocoumarin derivatives from Artemisia dracunculus , namely (−)-epoxyartemidin, (−)-2′-methoxydihydroartemidin, and (+)-3′-hydroxyartemidin were determined by chemical means via derivatization, kinetic racemate resolution ( Horeau method), and comparison of the circular dichroism (CD)

  合成了一系列3-羟基和3-溴丁基取代的香豆素。通过化学方法 通过 衍生化，动力学外消旋拆分（ Horeau方法）通过化学方法确定了来自 青蒿 的三种异香豆素衍生物的绝对构型 ，即（-）-环氧青蒿素，（-）-2'-甲氧基二氢青蒿素和（+）-3'-羟基 青蒿素。 ），以及圆二色性（CD）光谱的比较。
• Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies
  作者：Milena Simic、Nikola Paunovic、Ivan Boric、Jelena Randjelovic、Sandra Vojnovic、Jasmina Nikodinovic-Runic、Marina Pekmezovic、Vladimir Savic

  DOI：10.1016/j.bmcl.2015.08.086

  日期：2016.1

  A series of novel 3-substituted isocoumarins was prepared via Pd-catalysed coupling processes and screened in vitro for antifungal activity against Candida species. The study revealed antifungal potential of isocoumarins possessing the azole substituents, which, in some cases, showed biological properties equal to those of clinically used voriconazole. Selected compounds were also screened against voriconazole resistant Candida krusei 6258 and a clinical isolate Candida parapsilosis CA-27. Although the activity against these targets needs to be improved further, the results emphasise additional potential of this new class of antifungal compounds. (C) 2015 Elsevier Ltd. All rights reserved.