3,8-dimethyl-1-oxa-2,8-diazaspiro<4,5>dec-2-ene | 156339-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 3,8-dimethyl-1-oxa-2,8-diazaspiro<4,5>dec-2-ene
• 英文别名: 3,8-dimethyl-1-oxa-2,8-diazaspiro<4.5>dec-2-ene；3,8-Dimethyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene
• CAS: 156339-93-4
• 化学式: C₉H₁₆N₂O
• 分子量: 168.239
• InChiKey: NINLQTZTTDNQRO-UHFFFAOYSA-N

物化性质

• 沸点：
  236.3±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,8-dimethyl-1-oxa-2,8-diazaspiro<4,5>dec-2-ene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以40%的产率得到1-methyl-4-hydroxy-4-(2'-methyl-2'-aminoethyl)-piperidine
  参考文献：
  名称：

  Synthesis of spiro-substituted 1,3-oxazines by a new sequence leading to spiroheterocycles

  摘要：

  The target compounds, i.e. 1,3-oxazines which are spiro-substituted in position 6 by a piperidine moiety, are derived from 1-oxa-3,9-diaza-spiro [5.5]undecane, a novel heterocyclic parent system. They were all approached by the following three-step sequence: 1,3-dipolar cycloadditions of nitrile oxides and nitrones to piperidines bearing an exocyclic methylene group gave the corresponding spiro-substituted oxazole derivatives 3. In a consecutive step these were cleaved by hydrogenolysis to gamma-amino-alcohols 4, which in a final step were recyclized by insertions of a C-1-unit to yield the target structures 5-10: thus a de facto ring-extension of spiro-oxazoles to spiro-oxazines was accomplished.

  DOI：

  10.1007/bf00812705
• 作为产物：
  描述：

  1-甲基-4-亚甲基哌啶 、 乙醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 三乙胺 作用下， 生成 3,8-dimethyl-1-oxa-2,8-diazaspiro<4,5>dec-2-ene
  参考文献：
  名称：

  Cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine: Studies in regio- and stereoselectivity

  摘要：

  A series of spiro-substituted isoxazole derivatives were synthesized by 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine. Since nmr studies confirmed that only one regioisomer was formed selectively, semi-empirical quantum mechanical methods (AM1) were used to rationalize this regiochemical preference via calculation and inspection of HOMO-LUMO-energy and coefficients. X-ray structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calculated DELTAH(f)-values of all possible cycloadducts.

  DOI：

  10.1007/bf00811848

文献信息

• Fiera L., Sauter F., Froehlich J., Feng Y., Mereiter K., Monatsh. Chem, 125 (1994) N 8-9, S 909-919
  作者：Fiera L., Sauter F., Froehlich J., Feng Y., Mereiter K.

  DOI：——

  日期：——

表征谱图