7-Allyl-8-ethyl-3-oxa-2,7-diazabicyclo<3.3.0>octane | 120779-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: 7-Allyl-8-ethyl-3-oxa-2,7-diazabicyclo<3.3.0>octane
• 英文别名: (3aR,6S,6aR)-6-ethyl-5-prop-2-enyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c][1,2]oxazole
• CAS: 120779-70-6
• 化学式: C₁₀H₁₈N₂O
• 分子量: 182.266
• InChiKey: SDPFPHMHJYNHQB-LPEHRKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二烯丙基胺 在 氢氟酸 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 7-Allyl-8-ethyl-3-oxa-2,7-diazabicyclo<3.3.0>octane
  参考文献：
  名称：

  分子内肟烯烃环加成。立体形成官能化的吡咯烷。

  摘要：

  具有适当位置的醛肟或酮肟链的烯丙胺经历热诱导的偶极环加成反应形成双环异恶唑烷，并立体定向引入三个立体中心。这提供了进入立体特异性官能化的吡咯烷的入口。

  DOI：

  10.1016/s0040-4039(00)80746-7

文献信息

• Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction
  作者：Alfred Hassner、Rakesh Maurya、Oded Friedman、Hugo E. Gottlieb、Albert Padwa、David Austin

  DOI：10.1021/jo00069a011

  日期：1993.8

  Thermal intramolecular oxime olefin cycloaddition Of alpha-allylamino aldoximes and ketoximes 4 led stereospecifically to formation of oxadiazabicyclo[3.3.0]octanes 6. The presence of heteroatoms in these bicyclic fused 5-membered rings permits for the first time an evaluation of the conformation of this system by means of NMR. We found that some substituents in 6 restrict the conformational mobility of these five-membered rings to the extent that only one conformer was detected at 20-degrees-C. In other cases an equilibrium between two major conformers was revealed by NMR. Equilibrium measurements indicated a free energy of conversion of 13.2-13.4 kcal/mol, apparently a manifestation of the N-inversion in the isoxazolidine ring. NMR studies also showed that the NH-proton in isoxazolidines 6 prefers an axial orientation. Empirical force field data were adjusted for MM calculations in these bicyclic heterocycles. The MM2 force field with AMBER charge gave the best fit between calculated and experimental coupling constants.
• HASSNER, ALFRED;MAURYA, RAKESH;MESKO, ESZTER, TETRAHEDRON LETT., 29,(1988) N 41, C. 5313-5316
  作者：HASSNER, ALFRED、MAURYA, RAKESH、MESKO, ESZTER

  DOI：——

  日期：——