4-undecanoyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-undecanoyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one
• 英文别名: (6-Methoxy-3-oxo-1,4-benzoxazin-4-yl) undecanoate
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: QRSJFNXVNYSFFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  十一烷酸 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-undecanoyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  Optimization of Benzoxazinones as Natural Herbicide Models by Lipophilicity Enhancement

  摘要：

  Benzoxazinones are plant allelochemicals well-known for their phytotoxic activity and for taking part in the defense strategies of Gramineae, Ranunculaceae, and Scrophulariceae plants. These properties, in addition to the recently optimized methodologies for their large-scale isolation and synthesis, have made some derivatives of natural products, 2,4-dihydroxy-(2H)-1,4-benzoxazin-3-(4H)-one (DIBOA) and its 7-methoxy analogue ( DIMBOA), successful templates in the search for natural herbicide models. These new chemicals should be part of integrated methodologies for weed control. In ongoing research about the structure-activity relationships of benzoxazinones and the structural requirements for their phytotoxicity enhancement and after characterization of the optimal structural features, a new generation of chemicals with enhanced lipophilicity was developed. They were tested on selected standard target species and weeds in the search for the optimal aqueous solubility-lipophilicity rate for phytotoxicity. This physical parameter is known to be crucial in modern drug and agrochemical design strategies. The new compounds obtained in this way had interesting phytotoxicity profiles, empowering the phytotoxic effect of the starting benzoxazinone template in some cases. Quantitative structure-activity relationships were obtained by bioactivity-molecular parameters correlations. Because optimal lipophilicity values for phytotoxicity vary with the tested plant, these new derivatives constitute a more selective way to take advantage of benzoxazinone phytotoxic capabilities.

  DOI：

  10.1021/jf062168v

文献信息

• Optimization of Benzoxazinones as Natural Herbicide Models by Lipophilicity Enhancement
  作者：Francisco A. Macías、David Marín、Alberto Oliveros-Bastidas、José M. G. Molinillo

  DOI：10.1021/jf062168v

  日期：2006.12.1

  Benzoxazinones are plant allelochemicals well-known for their phytotoxic activity and for taking part in the defense strategies of Gramineae, Ranunculaceae, and Scrophulariceae plants. These properties, in addition to the recently optimized methodologies for their large-scale isolation and synthesis, have made some derivatives of natural products, 2,4-dihydroxy-(2H)-1,4-benzoxazin-3-(4H)-one (DIBOA) and its 7-methoxy analogue ( DIMBOA), successful templates in the search for natural herbicide models. These new chemicals should be part of integrated methodologies for weed control. In ongoing research about the structure-activity relationships of benzoxazinones and the structural requirements for their phytotoxicity enhancement and after characterization of the optimal structural features, a new generation of chemicals with enhanced lipophilicity was developed. They were tested on selected standard target species and weeds in the search for the optimal aqueous solubility-lipophilicity rate for phytotoxicity. This physical parameter is known to be crucial in modern drug and agrochemical design strategies. The new compounds obtained in this way had interesting phytotoxicity profiles, empowering the phytotoxic effect of the starting benzoxazinone template in some cases. Quantitative structure-activity relationships were obtained by bioactivity-molecular parameters correlations. Because optimal lipophilicity values for phytotoxicity vary with the tested plant, these new derivatives constitute a more selective way to take advantage of benzoxazinone phytotoxic capabilities.