7,7,1',2'-tetrahydro-7-deoxyagropyrenol | 1422458-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 7,7,1',2'-tetrahydro-7-deoxyagropyrenol
• 英文别名: (2R,3R)-5-(3-hydroxy-2-methylphenyl)pentane-2,3-diol
• CAS: 1422458-23-8
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: MCCAEHNRAKGNPY-BXKDBHETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,7,1',2'-tetrahydro-7-deoxyagropyrenol 、 乙酸酐 在 吡啶 作用下， 反应 1.5h， 以11 mg的产率得到[3-[(3R,4R)-3,4-diacetyloxypentyl]-2-methylphenyl] acetate
  参考文献：
  名称：

  Agropyrenol, a Phytotoxic Fungal Metabolite, and Its Derivatives: A Structure–Activity Relationship Study

  摘要：

  Agropyrenol is a phytotoxic substituted salicylic aldehyde produced in liquid culture by Ascochyta agropyrina var. nana, a potential mycoherbicide proposed for the control of the perennial weed Elytrigia repens. In this study, six derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on non-host weedy and agrarian plants, fungi, Gram-positive and Gram-negative bacteria, and brine shrimp larvae. The results provide insights into the structure-activity relationships of agropyrenol. Both the double bond and the diol system of the 3,4-dihydroxypentenyl side chain as well as the aldehyde group at C-1 of the phenolic ring of agropyrenol proved to be important for the phytotoxicity. The lesser polar 3',4'-O,O'-isopropylidene of agropyrenol also showed significant zootoxic and slight antimicrobial activities. This finding could be useful in devising new natural herbicides for practical application in agriculture.

  DOI：

  10.1021/jf304933z
• 作为产物：
  描述：

  agropyrenol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以2.5 mg的产率得到7,7,1',2'-tetrahydro-7-deoxyagropyrenol
  参考文献：
  名称：

  Agropyrenol, a Phytotoxic Fungal Metabolite, and Its Derivatives: A Structure–Activity Relationship Study

  摘要：

  Agropyrenol is a phytotoxic substituted salicylic aldehyde produced in liquid culture by Ascochyta agropyrina var. nana, a potential mycoherbicide proposed for the control of the perennial weed Elytrigia repens. In this study, six derivatives obtained by chemical modifications of the toxin were assayed for phytotoxic, antimicrobial, and zootoxic activities, and the structure-activity relationships were examined. Each compound was tested on non-host weedy and agrarian plants, fungi, Gram-positive and Gram-negative bacteria, and brine shrimp larvae. The results provide insights into the structure-activity relationships of agropyrenol. Both the double bond and the diol system of the 3,4-dihydroxypentenyl side chain as well as the aldehyde group at C-1 of the phenolic ring of agropyrenol proved to be important for the phytotoxicity. The lesser polar 3',4'-O,O'-isopropylidene of agropyrenol also showed significant zootoxic and slight antimicrobial activities. This finding could be useful in devising new natural herbicides for practical application in agriculture.

  DOI：

  10.1021/jf304933z