methyl 5-[(1R)-1-hydroxyethyl]-γ-oxofuran-2-butanoate | 1175564-31-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 5-[(1R)-1-hydroxyethyl]-γ-oxofuran-2-butanoate
• 英文别名: methyl 5-((1R)-1-hydroxyethyl)-gamma-oxofuran-2-butanoate；methyl 4-[5-[(1R)-1-hydroxyethyl]furan-2-yl]-4-oxobutanoate
• CAS: 1175564-31-4
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: GTUBQHDUMJNQSV-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-[(1R)-1-hydroxyethyl]-γ-oxofuran-2-butanoate 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  内生Diaporthe sp。的新的聚酮化合物。XZ-07

  摘要：

  Abstractmagnified imageFour new polyketides, namely rel‐(2R,3S,4R,5R)‐4‐ethyltetrahydro‐3‐methyl‐5‐propylfuran‐2,3‐diol (1), methyl 5‐[(1R)‐1‐hydroxyethyl]‐γ‐oxofuran‐2‐butanoate (2), butyl 5‐[(1R)‐1‐hydroxyethyl]‐γ‐oxofuran‐2‐butanoate (3), and 3,4‐dihydro‐5′‐[(1R)‐1‐hydroxyethyl][2,2′‐bifuran]‐5(2H)‐one (4), together with three known ones, 5‐[(1R)‐1‐hydroxethyl)‐γ‐oxofuran‐2‐butanoic acid (5), phomopsolide B (6), and (2S,3S)‐3,6‐dihydro‐6‐oxo‐2‐[(1E)‐2‐{(4S,5S)‐2,2,5‐trimethyl‐1,3‐dioxolan‐4‐yl]ethenyl}‐2H‐pyran‐3‐yl (2E)‐2‐methylbut‐2‐enoate (7), were isolated from the submerged cultures of the endophytic fungal strain Diaporthe sp. XZ‐07 of Camptotheca acuminate. The structures of the new compounds were established by 1D‐ and 2D‐NMR and MS data and by Mosher's method. Compound 6 significantly inhibited the growth of human‐tumor HeLa cells with an IC50 of 5.7 μg/ml by the MTT assay (MTT=3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide).

  DOI：

  10.1002/hlca.200800416