(3-Methyl-isoxazol-5-yl)-piperidin-1-yl-methanone | 950260-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3-Methyl-isoxazol-5-yl)-piperidin-1-yl-methanone
• 英文别名: (3-Methyl-1,2-oxazol-5-yl)-piperidin-1-ylmethanone
• CAS: 950260-22-7
• 化学式: C₁₀H₁₄N₂O₂
• mdl: MFCD13513757
• 分子量: 194.233
• InChiKey: XDZQCINBCFGORM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-Methyl-isoxazol-5-yl)-piperidin-1-yl-methanone 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以85%的产率得到3-methyl-5-piperidinomethylisoxazole
  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：

  ethyl-4-hydroximino-2-oxopentanoate 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (3-Methyl-isoxazol-5-yl)-piperidin-1-yl-methanone
  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

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.