6-methyl-5-oxa-6-azadispiro<2.3.4.0>undecane | 143446-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 6-methyl-5-oxa-6-azadispiro<2.3.4.0>undecane
• 英文别名: 9-Methyl-10-oxa-9-azadispiro[2.0.44.33]undecane
• CAS: 143446-60-0
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: OJHULUIZCVVGHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-cyclopentylidenemethanamine N-oxide 、 亚甲基环丙烷 以 苯 为溶剂， 反应 24.0h， 生成 6-methyl-5-oxa-6-azadispiro<2.3.4.0>undecane 、 5-methyl-4-oxa-5-azadispiro<2.2.4.0>undecane
  参考文献：
  名称：

  Rearrangement of isoxazoline-5-spiro derivatives. 8. Selective formation of tetrahydropyridones from C,C-disubstituted nitrones

  摘要：

  The thermal rearrangement of isoxazolidines 3, 7, 9, 17, and 19 obtained by 1,3-dipolar cycloaddition of C,C-disubstituted nitrones and methylenecyclopropanes 1 and 6 has been studied. The lack of hydrogen at the C-3 position of the isoxazolidine ring leads selectively to azaheterocyclic ketones, structurally differentiated according to the stating dipoles and dipolarophiles. The process allows the "one-pot" synthesis of valuable perhydro pyridone, indolizinone, and pyrrolo[1,2-a]quinolinone ring systems with excellent overall yield and atom economy. A new entry to the functionalized 1-azaspiro[5.5]undecane 22 framework found in alkaloids of the histrionicotoxin family is also presented.

  DOI：

  10.1021/jo00047a019