methyl 3-tert-butylcarboxamido-5-methyl-4-isoxazolecarboxylate | 135400-60-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 3-tert-butylcarboxamido-5-methyl-4-isoxazolecarboxylate
• 英文别名: Methyl 3-(tert-butylcarbamoyl)-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 135400-60-1
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: XZJXHOTXPQDOFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-tert-butylcarboxamido-5-methyl-4-isoxazolecarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以91%的产率得到3-tert-butylcarboxamido-5-methyl-4-isoxazolecarboxylic acid
  参考文献：
  名称：

  异恶唑和吡唑的3-甲酰胺基-4-羧酸衍生物的新合成入口

  摘要：

  2-氨基-3-甲氧基羰基-4-氧代-2-戊烯酸乙酯（3）与羟胺或肼反应，分别得到异恶唑和吡唑原二羧酸酯4和5。二酯4和5的部分水解得到相应的二羧酸单酯6和7。中间体酰氯8，9的酰胺化，随后4-甲基酯10、11的水解分别得到标题化合物1和2。

  DOI：

  10.1002/jhet.5570370129
• 作为产物：
  描述：

  3-乙基4-甲基5-甲基-1,2-恶唑-3,4-二羧酸酯 在 氢氧化钾 、 五氯化磷 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 29.0h， 生成 methyl 3-tert-butylcarboxamido-5-methyl-4-isoxazolecarboxylate
  参考文献：
  名称：

  异恶唑和吡唑的3-甲酰胺基-4-羧酸衍生物的新合成入口

  摘要：

  2-氨基-3-甲氧基羰基-4-氧代-2-戊烯酸乙酯（3）与羟胺或肼反应，分别得到异恶唑和吡唑原二羧酸酯4和5。二酯4和5的部分水解得到相应的二羧酸单酯6和7。中间体酰氯8，9的酰胺化，随后4-甲基酯10、11的水解分别得到标题化合物1和2。

  DOI：

  10.1002/jhet.5570370129

文献信息

• Synthesis and herbicidal activity of isoxazoledicarboxylic acid derivatives
  作者：Peter Münster、Wolfgang Freund、Volker Maywald、Thomas Kükenhöhner、Matthias Gerber、Klaus Grossmann、Helmut Walter

  DOI：10.1002/ps.2780440104

  日期：1995.5

  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.
• A new synthetic entry to 3-carboxamido-4-carboxylic acid derivatives of isoxazole and pyrazole
  作者：Chiara B. Vicentini、Manuela Mazzanti、Carlo F. Morelli、Maurizio Manfrini

  DOI：10.1002/jhet.5570370129

  日期：2000.1

  2-amino-3-methoxycarbonyl-4-oxo-2-pentenoate (3) reacts with hydroxylamine or hydrazines to give isoxazole and pyrazole ortho-dicarboxylic acid esters 4 and 5, respectively. Partial hydrolysis of diesters 4 and 5 afforded the corresponding dicarboxylic acid monoesters 6 and 7. Amidation of the intermediate acid chlorides 8,9 followed by hydrolysis of 4-methylesters 10, 11 gave the title compounds 1 and

  2-氨基-3-甲氧基羰基-4-氧代-2-戊烯酸乙酯（3）与羟胺或肼反应，分别得到异恶唑和吡唑原二羧酸酯4和5。二酯4和5的部分水解得到相应的二羧酸单酯6和7。中间体酰氯8，9的酰胺化，随后4-甲基酯10、11的水解分别得到标题化合物1和2。