6-chloro-4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one | 1204325-77-8

• 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: 6-chloro-4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one
• 英文别名: 6-Cl-4-Val-D-DIBOA；(6-chloro-3-oxo-1,4-benzoxazin-4-yl) pentanoate
• CAS: 1204325-77-8
• 化学式: C₁₃H₁₄ClNO₄
• 分子量: 283.711
• InChiKey: JLMUTZRHFKPFRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基-6-氯-2,3-二氢-4H-1,4-苯并恶嗪-3-酮 、 戊酰氯 在 吡啶 作用下， 以99%的产率得到6-chloro-4-valeroyloxy-(2H)-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  Combined Strategy for Phytotoxicity Enhancement of Benzoxazinones

  摘要：

  Fifteen new derivatives of D-DIBOA, including aromatic ring modifications and the addition of side chains in positions C-2 and N-4, were synthesized and their phytotoxicity, selectivity, and structure-activity relationships evaluated. The most active compounds among the derivatives at the C-2 position were 6-Cl-2-Et-D-DIBOA and 6-F-2-Et-D-DIBOA. Of the derivatives at N-4, the most active compounds were 6-Cl-4-Pr-D-DIBOA and 6-Cl-4-Val-D-DIBOA. These four compounds showed high levels of inhibition in root length at very low concentrations in all species. The most remarkable result is the 70% inhibition observed for the root length of cress at 100 nM caused by the latter two compounds. These results support our previous research and conclusions regarding the steric, electronic, and solubility requirements to achieve the maximum phytotoxic activity.

  DOI：

  10.1021/jf903445m

文献信息

• Combined Strategy for Phytotoxicity Enhancement of Benzoxazinones
  作者：Francisco A. Macías、Nuria Chinchilla、Elena Arroyo、José M. G. Molinillo、David Marín、Rosa M. Varela

  DOI：10.1021/jf903445m

  日期：2010.2.10

  Fifteen new derivatives of D-DIBOA, including aromatic ring modifications and the addition of side chains in positions C-2 and N-4, were synthesized and their phytotoxicity, selectivity, and structure-activity relationships evaluated. The most active compounds among the derivatives at the C-2 position were 6-Cl-2-Et-D-DIBOA and 6-F-2-Et-D-DIBOA. Of the derivatives at N-4, the most active compounds were 6-Cl-4-Pr-D-DIBOA and 6-Cl-4-Val-D-DIBOA. These four compounds showed high levels of inhibition in root length at very low concentrations in all species. The most remarkable result is the 70% inhibition observed for the root length of cress at 100 nM caused by the latter two compounds. These results support our previous research and conclusions regarding the steric, electronic, and solubility requirements to achieve the maximum phytotoxic activity.