[(2S)-5-[(3R)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]pentan-2-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate | 1431159-72-6

• 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: [(2S)-5-[(3R)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]pentan-2-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
• CAS: 1431159-72-6
• 化学式: C₂₅H₂₇F₃O₆
• 分子量: 480.481
• InChiKey: YAQFDNXQRZUIJU-LSRZYVKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (R)-3-((S)-4-hydroxypentyl)-8-methoxyisochroman-1-one 、 甲氧基-三氟甲基苯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 14.0h， 生成 [(2S)-5-[(3R)-8-methoxy-1-oxo-3,4-dihydroisochromen-3-yl]pentan-2-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Isocoumarin Derivatives and Benzofurans from a Sponge-Derived Penicillium sp. Fungus

  摘要：

  Ten new fungal metabolites, including three hydroisocoumarins, penicimarins A-C (1-3), three isocoumarins, penicimarins D-F (6-8), and four benzofurans, penicifurans A-D (11-14), together with four known isocoumarin derivatives (4, 5, 9, 10), were obtained from the sponge derived fungus Pen icillium sp. MWZ14-4, collected from the South China Sea. Their planar structures and relative configurations were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-4 were assigned by the modified Mosher 's method and TDDFT ECD calculations together with comparison of their CD spectra. Compound 1 represents a rare naturally occurring isocournarin derivative with 4-substitution, but no substituent at the 3-position. These compounds were evaluated for antibacterial activities and cytotoxic activities in vitro. Among them, penicifuran A (11) exhibited inhibitory activity against Staphylococcus albus with an MIC value of 3.13 mu M.

  DOI：

  10.1021/np3007556

文献信息

• Isocoumarin Derivatives and Benzofurans from a Sponge-Derived <i>Penicillium</i> sp. Fungus
  作者：Jun Qi、Chang-Lun Shao、Zhi-Yong Li、Li-She Gan、Xiu-Mei Fu、Wen-Tao Bian、Hong-Ying Zhao、Chang-Yun Wang

  DOI：10.1021/np3007556

  日期：2013.4.26

  Ten new fungal metabolites, including three hydroisocoumarins, penicimarins A-C (1-3), three isocoumarins, penicimarins D-F (6-8), and four benzofurans, penicifurans A-D (11-14), together with four known isocoumarin derivatives (4, 5, 9, 10), were obtained from the sponge derived fungus Pen icillium sp. MWZ14-4, collected from the South China Sea. Their planar structures and relative configurations were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-4 were assigned by the modified Mosher 's method and TDDFT ECD calculations together with comparison of their CD spectra. Compound 1 represents a rare naturally occurring isocournarin derivative with 4-substitution, but no substituent at the 3-position. These compounds were evaluated for antibacterial activities and cytotoxic activities in vitro. Among them, penicifuran A (11) exhibited inhibitory activity against Staphylococcus albus with an MIC value of 3.13 mu M.