5-hydroxymethylmellein | 88037-93-8

• 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: 5-hydroxymethylmellein
• 英文别名: (R)-5-hydroxymethylmellein；(3R)-8-hydroxy-5-(hydroxymethyl)-3-methyl-3,4-dihydroisochromen-1-one
• CAS: 88037-93-8
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: OALPOISXSLLKCP-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxymethylmellein 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 5-甲基蜂蜜曲菌素
  参考文献：
  名称：

  Structures and Phytotoxicity of Metabolites fromValsa ceratosperma

  摘要：

  Valsa ceratosperma, which is the pathogenic fungus of apple canker, was grown in a synthetic medium. The neutral extract from the culture filtrate was chromatographed on a silica gel column to give five isocoumarins. Their structures were determined by MS, UV, IR, 1H and 13C NMR, and CD spectra. Three of them were known compounds; ( − )-5-methylmellein (1), ( − )-5-carboxylmellein (2) and ( − )-5-hydroxylmethylmellein (3). Since the absolute configurations at C-3 in 2 and 3 were not known until now, both were determined to be R by chemical correlations. The two were new compounds; ( + )-(3R,4S)-trans-4-hydroxy-5-methylmellein (4) and ( − )-(3R,4R)-cis-4-hydroxy-5-methylmellein (5). All the five compounds showed phytotoxicity in a bioassay using detached apple shoots and lettuce seedlings.

  DOI：

  10.1080/00021369.1986.10867484