2-methoxy-5-(7-methyl-3-methylene-oct-6-en-1-ynyl)hex-4-ene-1,3,6-triol | 1461727-09-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methoxy-5-(7-methyl-3-methylene-oct-6-en-1-ynyl)hex-4-ene-1,3,6-triol
• CAS: 1461727-09-2
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: KXQDKQIMGIPTHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (-)-phomentrioloxin 在 sodium periodate 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以3 mg的产率得到2-methoxy-5-(7-methyl-3-methylene-oct-6-en-1-ynyl)hex-4-ene-1,3,6-triol
  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