ethyl-4-hydroximino-2-oxopentanoate | 13081-00-0

• 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: ethyl-4-hydroximino-2-oxopentanoate
• 英文别名: Ethyl-(α-hydroxyiminoethyl)pyruvat；Ethyl 4-hydroxyimino-2-oxovalerat；Ethyl 4-(hydroxyimino)-2-oxopentanoate；ethyl 4-hydroxyimino-2-oxopentanoate
• CAS: 13081-00-0
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: JHSVLBKMXGDWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl-4-hydroximino-2-oxopentanoate 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以84%的产率得到3-甲基-5-异噁唑羧酸甲酯
  参考文献：
  名称：

  Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: synthesis and muscarinic activity

  摘要：

  A series of 3-, 4- and 5-aminomethyl isoxazoles and isoxazoles with one or two additional methyl groups at the heterocycle were synthesized in order to investigate the structural requirements, ie heterocyclic moiety, regiochemistry and length of an aminoalkyl unit, for muscarinic activity. This was assayed on isolated rabbit vas deferens (M(1) receptor subtype) and isolated guinea-pig atrium (M(2) receptor subtype) and ileum (M(3) receptor subtype). The isoxazoles tested are one to three orders of magnitude less active than furane or oxadiazole derivatives, having similar structural characteristics except for the heterocycle. Thus, the differences in molecular point charges and charge distribution contribute to the muscarinic activity of these compounds more than small differences in molecular shape and conformational energies.

  DOI：

  10.1016/0223-5234(96)88303-6
• 作为产物：
  描述：

  乙酰丙酮酸乙酯 在 sodium hydroxide 、 盐酸羟胺 作用下， 反应 2.0h， 以72%的产率得到ethyl-4-hydroximino-2-oxopentanoate
  参考文献：
  名称：

  New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents

  摘要：

  We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2,6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.

  DOI：

  10.1016/0223-5234(92)90137-p

文献信息

• Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: synthesis and muscarinic activity
  作者：G Dannhardt、W Kiefer、G Lambrecht、S Laufer、E Mutschler、J Schweiger、H.G. Striegel

  DOI：10.1016/0223-5234(96)88303-6

  日期：1995.1

  A series of 3-, 4- and 5-aminomethyl isoxazoles and isoxazoles with one or two additional methyl groups at the heterocycle were synthesized in order to investigate the structural requirements, ie heterocyclic moiety, regiochemistry and length of an aminoalkyl unit, for muscarinic activity. This was assayed on isolated rabbit vas deferens (M(1) receptor subtype) and isolated guinea-pig atrium (M(2) receptor subtype) and ileum (M(3) receptor subtype). The isoxazoles tested are one to three orders of magnitude less active than furane or oxadiazole derivatives, having similar structural characteristics except for the heterocycle. Thus, the differences in molecular point charges and charge distribution contribute to the muscarinic activity of these compounds more than small differences in molecular shape and conformational energies.
• New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents
  作者：F Lepage、F Tombret、G Cuvier、A Marivain、JM Gillardin

  DOI：10.1016/0223-5234(92)90137-p

  日期：1992.9

  We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2,6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.