dimethyl 3-(2,4-dichlorophenyl)isoxazole-4,5-dicarboxylate | 134516-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 3-(2,4-dichlorophenyl)isoxazole-4,5-dicarboxylate
• 英文别名: Dimethyl 3-(2,4-dichlorophenyl)-1,2-oxazole-4,5-dicarboxylate
• CAS: 134516-40-8
• 化学式: C₁₃H₉Cl₂NO₅
• 分子量: 330.124
• InChiKey: RKIDLHSRDYXSHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 3-(2,4-dichlorophenyl)isoxazole-4,5-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 5-tert-Butylcarbamoyl-3-(2,4-dichloro-phenyl)-isoxazole-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and herbicidal activity of isoxazoledicarboxylic acid derivatives

  摘要：

  AbstractStarting from bulk chemicals, novel isoxazoledicarboxylic acid esters were prepared and converted to the corresponding dicarboxylic acid mono‐amides in a few reaction steps and in high overall yields. Key intermediates for the cycloaddition step were chlorooximinoacetates or amides as nitrile oxide equivalents, prepared in one‐pot reactions from diketene or acetoacetic acid esters. Isoxazoledicarboxylic acid monoamides combined good herbicidal activity with chemical flexibility. They were characterized as inhibitors of photosynthesis. Particularly, they affected the photosynthetic electron transport in photosystem II and the rate of carbon dioxide assimilation. Applied post‐emergence, the new compounds were found to control a broad spectrum of key weeds in corn. Excellent activity was found on Abutilon theophrasti (L.) Medik., Amaranthus retroflexus L., Chenopodium album L., Ipomoea spp., Polygonum persicaria L., Solanum nigrum L. and Xanthium strumarium L. with rates between 0.2 and 0.5 kg ha−1. As a side‐effect, the compounds also showed activity against grass weeds. The compounds are excellent tank‐mix partners, e.g. for sulfonyl‐ureas, to complete the weed spectrum (Chenopodium album L., Solanum nigrum L.) and/or to reduce the risk of developing herbicide‐resistant weeds.

  DOI：

  10.1002/ps.2780440104
• 作为产物：
  描述：

  2,4-二氯苯甲醛肟 、 丁炔二酸二甲酯 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以84%的产率得到dimethyl 3-(2,4-dichlorophenyl)isoxazole-4,5-dicarboxylate
  参考文献：
  名称：

  4,5-二取代的吡咯烷2,3-二酮的杂环-杂环策略：来自异恶唑酯的还原重排方法

  摘要：

  这项工作证明了杂环-杂环互变策略可以以中等至良好的收率（50-80％）获得4,5-二取代的3-羟基-2-吡咯烷酮。该方法相对于多组分反应方法具有明显的优点，因为它允许在氮位置获得未取代的3-羟基-2-吡咯烷酮以进一步官能化。

  DOI：

  10.1055/a-1492-8216