8-Hydroxy-3-{(E)-(S)-3-hydroxy-4-[(2R,3R)-3-((R)-2-hydroxy-propyl)-oxiranyl]-but-1-enyl}-6-methoxy-isochromen-1-one | 910482-50-7

• 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: 8-Hydroxy-3-{(E)-(S)-3-hydroxy-4-[(2R,3R)-3-((R)-2-hydroxy-propyl)-oxiranyl]-but-1-enyl}-6-methoxy-isochromen-1-one
• 英文别名: 8-hydroxy-3-[(E,3S)-3-hydroxy-4-[(2R,3R)-3-[(2R)-2-hydroxypropyl]oxiran-2-yl]but-1-enyl]-6-methoxyisochromen-1-one
• CAS: 910482-50-7
• 化学式: C₁₉H₂₂O₇
• 分子量: 362.379
• InChiKey: XGBDRADUXKNAMY-MCDIIMPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-Hydroxy-3-{(E)-(S)-3-hydroxy-4-[(2R,3R)-3-((R)-2-hydroxy-propyl)-oxiranyl]-but-1-enyl}-6-methoxy-isochromen-1-one 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以1.6 mg的产率得到(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(S)-3-(8-hydroxy-6-methoxy-1-oxo-1H-isochromen-3-yl)-1-{(2R,3R)-3-[(R)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-propyl]-oxiranylmethyl}-allyl ester
  参考文献：
  名称：

  Five new isocoumarins from Sonoran desert plant-associated fungal strains Paraphaeosphaeria quadriseptata and Chaetomium chiversii

  摘要：

  Five new isocoumarins, paraphaeosphaerins A-C and chaetochiversins A and B, biogenetically related to monocillin I and radicicol, have been isolated from solid agar cultures of Paraphaeosphaeria quadriseptata and Chaetomium chiversii, two fungal strains living in association with the Sonoran desert plants, Opuntia leptocaulis and Ephedra fasciculata, respectively. A new chroman-4-one, a osphaerin C, was also isolated from P. quadriseptata. Their structures and stereochemistry were elucidated using a combination of H-1 and C-13 homo- and hetero-nuclear 2D NMR techniques, H-1 NMR analysis of Mosher's esters, and chemical correlations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.089
• 作为产物：
  描述：

  3-(3'S,8'R-dihydroxy-5'R,6'R-oxirenonona-1'E-enyl)-6,8-dihydroxy-isochromen-1-one 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以2.1 mg的产率得到8-Hydroxy-3-{(E)-(S)-3-hydroxy-4-[(2R,3R)-3-((R)-2-hydroxy-propyl)-oxiranyl]-but-1-enyl}-6-methoxy-isochromen-1-one
  参考文献：
  名称：

  Five new isocoumarins from Sonoran desert plant-associated fungal strains Paraphaeosphaeria quadriseptata and Chaetomium chiversii

  摘要：

  Five new isocoumarins, paraphaeosphaerins A-C and chaetochiversins A and B, biogenetically related to monocillin I and radicicol, have been isolated from solid agar cultures of Paraphaeosphaeria quadriseptata and Chaetomium chiversii, two fungal strains living in association with the Sonoran desert plants, Opuntia leptocaulis and Ephedra fasciculata, respectively. A new chroman-4-one, a osphaerin C, was also isolated from P. quadriseptata. Their structures and stereochemistry were elucidated using a combination of H-1 and C-13 homo- and hetero-nuclear 2D NMR techniques, H-1 NMR analysis of Mosher's esters, and chemical correlations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.089

文献信息

• Five new isocoumarins from Sonoran desert plant-associated fungal strains Paraphaeosphaeria quadriseptata and Chaetomium chiversii
  作者：E. M. Kithsiri Wijeratne、Priyani A. Paranagama、A. A. Leslie Gunatilaka

  DOI：10.1016/j.tet.2006.06.089

  日期：2006.9

  Five new isocoumarins, paraphaeosphaerins A-C and chaetochiversins A and B, biogenetically related to monocillin I and radicicol, have been isolated from solid agar cultures of Paraphaeosphaeria quadriseptata and Chaetomium chiversii, two fungal strains living in association with the Sonoran desert plants, Opuntia leptocaulis and Ephedra fasciculata, respectively. A new chroman-4-one, a osphaerin C, was also isolated from P. quadriseptata. Their structures and stereochemistry were elucidated using a combination of H-1 and C-13 homo- and hetero-nuclear 2D NMR techniques, H-1 NMR analysis of Mosher's esters, and chemical correlations. (c) 2006 Elsevier Ltd. All rights reserved.