4,8-dihydroxy-3-((R)-2-hydroxypentyl)-6,7-dimethoxyisochroman-1-one | 1033204-25-9

• 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: 4,8-dihydroxy-3-((R)-2-hydroxypentyl)-6,7-dimethoxyisochroman-1-one
• 英文别名: (3R,4R)-4,8-dihydroxy-3-((R)-2-hydroxypentyl)-6,7-dimethoxyisochroman-1-one；(3R,4R)-4,8-dihydroxy-6,7-dimethoxy-3-((R)-2-hydroxypentyl)isochroman-1-one；fusarentin；(3R,4R)-4,8-dihydroxy-3-[(2R)-2-hydroxypentyl]-6,7-dimethoxy-3,4-dihydroisochromen-1-one
• CAS: 1033204-25-9
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: YVVVQBLWJYKSII-ZDSQKVDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,8-dihydroxy-3-((R)-2-hydroxypentyl)-6,7-dimethoxyisochroman-1-one 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 以62%的产率得到
  参考文献：
  名称：

  Bioactive Isocoumarins Isolated from the Endophytic Fungus Microdochium bolleyi

  摘要：

  Three new isocoumarin derivatives (2-4) were isolated together with monocerin (1) from Microdochium bolleyi, an endophytic fungus from Fagonia cretica, a herbaceous plant of the semiarid coastal regions of Gomera. Compounds 2 and 3 are both 12-oxo epimers of 1, and 4 is a ring-opened derivative of 1. The structures were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations were determined by a modified Mosher's method. Compounds 1, 3, and 4 showed good antifungal, antibacterial, and antialgal activities against Microbotryum violaceum, Escherichia coli, Bacillus megaterium, and Chlorella fusca. Compound 2 was moderately antifungal and antialgal.

  DOI：

  10.1021/np800095g
• 作为产物：
  描述：

  (3R,4R)-4,8-diacetoxy-6,7-dimethoxy-3-((R)-2-hydroxypentyl)isochroman-1-one 在 potassium carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以76%的产率得到4,8-dihydroxy-3-((R)-2-hydroxypentyl)-6,7-dimethoxyisochroman-1-one
  参考文献：
  名称：

  手性高价碘不对称合成4,8-二羟基异色满-1-酮聚酮化合物

  摘要：

  用手性高价碘对正链烯基苯甲酸酯进行立体选择性氧化内酯化，可用于不对称合成4-羟基异色满-1-酮聚酮化合物，包括4-羟基水elle素（1），富沙仑丁2的衍生物，单甘油（3）和单甘油的差向异构体。Epi - 3。

  DOI：

  10.1021/ol300185u

文献信息

• Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide Metabolites Using Chiral Hypervalent Iodine(III)
  作者：Morifumi Fujita、Kazuhiro Mori、Mio Shimogaki、Takashi Sugimura

  DOI：10.1021/ol300185u

  日期：2012.3.2

  Stereoselective oxylactonization of ortho-alkenylbenzoate with chiral hypervalent iodine is applied to the asymmetric synthesis of 4-oxyisochroman-1-one polyketide metabolites including 4-hydroxymellein (1), a derivative of fusarentin 2, monocerin (3), and an epimer of monocerin epi-3.

  用手性高价碘对正链烯基苯甲酸酯进行立体选择性氧化内酯化，可用于不对称合成4-羟基异色满-1-酮聚酮化合物，包括4-羟基水elle素（1），富沙仑丁2的衍生物，单甘油（3）和单甘油的差向异构体。Epi - 3。
• Bioactive Isocoumarins Isolated from the Endophytic Fungus <i>Microdochium bolleyi</i>
  作者：Wen Zhang、Karsten Krohn、Siegfried Draeger、Barbara Schulz

  DOI：10.1021/np800095g

  日期：2008.6.1

  Three new isocoumarin derivatives (2-4) were isolated together with monocerin (1) from Microdochium bolleyi, an endophytic fungus from Fagonia cretica, a herbaceous plant of the semiarid coastal regions of Gomera. Compounds 2 and 3 are both 12-oxo epimers of 1, and 4 is a ring-opened derivative of 1. The structures were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configurations were determined by a modified Mosher's method. Compounds 1, 3, and 4 showed good antifungal, antibacterial, and antialgal activities against Microbotryum violaceum, Escherichia coli, Bacillus megaterium, and Chlorella fusca. Compound 2 was moderately antifungal and antialgal.