(6aR,9S,9aS)-3-[(1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl]-6a-methyl-9-[(2S)-2-methyloctanoyl]-9,9adihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione | 1469746-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6aR,9S,9aS)-3-[(1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl]-6a-methyl-9-[(2S)-2-methyloctanoyl]-9,9adihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione
• 英文别名: cohaerin G；Cohaerin G；(6aR,9S,9aS)-3-[(1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl]-6a-methyl-9-[(2S)-2-methyloctanoyl]-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione
• CAS: 1469746-33-5
• 化学式: C₂₈H₃₆O₇
• 分子量: 484.59
• InChiKey: UXVBLOOVEHJYRA-OQNBJDIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6aR,9S,9aS)-3-[(1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl]-6a-methyl-9-[(2S)-2-methyloctanoyl]-9,9adihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione 、 甲氧基-三氟甲基苯 以 氘代吡啶 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Cohaerins G–K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C–K

  摘要：

  Four azaphilones, for which the trivial names cohaerins G, H, I and K are proposed, were isolated from the methanolic stromatal extract of Annulohypoxylon cohaerens together with the known metabolites cohaerins C-F and 4,5,4',5'-tetrahydroxy-1,1'-binaphthyl (BNT). Their planar structures were determined by NMR spectroscopy and by mass spectrometry. While their core structure is identical with cohaerin C and F, respectively, subgroups 2-hydroxy-6-methylphenyl and (1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl account for the structural diversity as substituents at C-3 of the azaphilone core. The absolute stereochemistry was assigned by NOE NMR experiments, CD spectroscopy and derivatisation with Mosher's acid; in addition, the stereochemistry of cohaerins C-F was revised. The metabolites showed cytotoxic effects besides a weak antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.07.027

文献信息

• Cohaerins G–K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C–K
  作者：Frank Surup、Kathrin I. Mohr、Rolf Jansen、Marc Stadler

  DOI：10.1016/j.phytochem.2013.07.027

  日期：2013.11

  Four azaphilones, for which the trivial names cohaerins G, H, I and K are proposed, were isolated from the methanolic stromatal extract of Annulohypoxylon cohaerens together with the known metabolites cohaerins C-F and 4,5,4',5'-tetrahydroxy-1,1'-binaphthyl (BNT). Their planar structures were determined by NMR spectroscopy and by mass spectrometry. While their core structure is identical with cohaerin C and F, respectively, subgroups 2-hydroxy-6-methylphenyl and (1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl account for the structural diversity as substituents at C-3 of the azaphilone core. The absolute stereochemistry was assigned by NOE NMR experiments, CD spectroscopy and derivatisation with Mosher's acid; in addition, the stereochemistry of cohaerins C-F was revised. The metabolites showed cytotoxic effects besides a weak antimicrobial activity. (C) 2013 Elsevier Ltd. All rights reserved.