(-)-phomentrioloxin | 1380508-49-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-phomentrioloxin
• 英文别名: (1R,2R,3R,4R)-3-methoxy-6-(7-methyl-3-methylideneoct-6-en-1-ynyl)cyclohex-5-ene-1,2,4-triol
• CAS: 1380508-49-5
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: QMURELAJMFSPEF-QBPKDAKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-phomentrioloxin 在 5% rhodium-on-charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 以3 mg的产率得到1′,1′,2′,2′,3′,8′,6′,7′-octahydrophomentrioloxin
  参考文献：
  名称：

  Phomentrioloxin, a Fungal Phytotoxin with Potential Herbicidal Activity, and its Derivatives: A Structure–Activity Relationship Study

  摘要：

  Phomentrioloxin is a phytotoxic geranylcyclohexenetriol produced in liquid culture by Phomopsis sp. (teleomorph: Diaporthe gulyae), a potential mycoherbicide proposed for the control of the annual weed Carthamus lanatus. In this study, seven 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 nonhost weedy and agrarian plants, fungi, Gram+ and Gram- bacteria, and on brine shrimp larvae. The results provide insights into an investigation of the structural requirements for activity. The hydroxy groups at C-2 and C-4 appeared to be important features for the phytotoxicity, as well as an unchanged cyclohexentriol ring. A role seemed also to be played by the unsaturations of the geranyl side chain. These findings could be useful for understanding the mechanisms of action of new natural products, for identifying the active sites, and possibly in devising new herbicides of natural origin.

  DOI：

  10.1021/jf4030618
• 作为产物：
  描述：

  (+)-顺式-2(s),3(s)-2,3-二羟基-2,3-二氢碘苯 在 2,6-二甲基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四氧化锇 、 水 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二乙胺 、 丙酮 、 mineral oil 为溶剂， 反应 47.0h， 生成 (-)-phomentrioloxin
  参考文献：
  名称：

  Chemoenzymatic Total Synthesis of the Phytotoxic Geranylcyclohexentriol (−)-Phomentrioloxin

  摘要：

  The enantiomeric form, 1R, of the structure (IS) assigned to the phytotoxic natural product phomentrioloxin has been synthesized in seven steps from the homochiral cis-1,2-dihydrocatechol 3. These studies reveal that the true structure of phomentrioloxin is represented by 1R and not by 1S.

  DOI：

  10.1021/np4002866

文献信息

• Chemoenzymatic Total Synthesis of the Phytotoxic Geranylcyclohexentriol (−)-Phomentrioloxin
  作者：Xinghua Ma、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/np4002866

  日期：2013.8.23

  The enantiomeric form, 1R, of the structure (IS) assigned to the phytotoxic natural product phomentrioloxin has been synthesized in seven steps from the homochiral cis-1,2-dihydrocatechol 3. These studies reveal that the true structure of phomentrioloxin is represented by 1R and not by 1S.
• Phomentrioloxin, a Fungal Phytotoxin with Potential Herbicidal Activity, and its Derivatives: A Structure–Activity Relationship Study
  作者：Alessio Cimmino、Anna Andolfi、Maria Chiara Zonno、Angela Boari、Ciro Troise、Andrea Motta、Maurizio Vurro、Gavin Ash、Antonio Evidente

  DOI：10.1021/jf4030618

  日期：——

  Phomentrioloxin is a phytotoxic geranylcyclohexenetriol produced in liquid culture by Phomopsis sp. (teleomorph: Diaporthe gulyae), a potential mycoherbicide proposed for the control of the annual weed Carthamus lanatus. In this study, seven 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 nonhost weedy and agrarian plants, fungi, Gram+ and Gram- bacteria, and on brine shrimp larvae. The results provide insights into an investigation of the structural requirements for activity. The hydroxy groups at C-2 and C-4 appeared to be important features for the phytotoxicity, as well as an unchanged cyclohexentriol ring. A role seemed also to be played by the unsaturations of the geranyl side chain. These findings could be useful for understanding the mechanisms of action of new natural products, for identifying the active sites, and possibly in devising new herbicides of natural origin.