1,7-Diphenyl-3-oxa-2,7-diazabicyclo<3.3.0>octane | 120779-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,7-Diphenyl-3-oxa-2,7-diazabicyclo<3.3.0>octane
• 英文别名: (3aS,6aR)-5,6a-diphenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c][1,2]oxazole
• CAS: 120779-84-2
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: FMJHLGKAEZDCOS-WBVHZDCISA-N

物化性质

• 沸点：
  408.0±55.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,7-Diphenyl-3-oxa-2,7-diazabicyclo<3.3.0>octane 在 lithium aluminium tetrahydride 作用下， 生成 [(3S,4R)-4-amino-1,4-diphenylpyrrolidin-3-yl]methanol
  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
• 作为产物：
  描述：

  N-Allyl-N-phenyl-1-amino-2-acetophenone 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 11.0h， 生成 1,7-Diphenyl-3-oxa-2,7-diazabicyclo<3.3.0>octane
  参考文献：
  名称：

  Stereochemistry. 82. Conformation of fused five-membered heterocyclic rings derived from the intramolecular oxime olefin cycloaddition reaction

  摘要：

  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.

  DOI：

  10.1021/jo00069a011

文献信息

• NH-Isoxazolo-bicycles; new molecular scaffolds for organocatalysis
  作者：Linda Doyle、Frances Heaney

  DOI：10.1016/j.tet.2011.01.034

  日期：2011.3

  A new scaffold for organocatalysis of the Diels-Alder reaction is disclosed; an isoxazolidine ring forms the core of the catalyst and its activity is enhanced by judicious fusion of a second five-membered heterocycle to the c-edge. The catalyst performance is improved by the incorporation of an endo-cyclic electron withdrawing group adjacent to the fusion point. The organic core is effective only in the presence of an acid co-catalyst and whilst the two-component system shows potential as an enantioselective catalyst it is demonstrated that stereocontrol is a feature of the organic core and is fully independent of the choice of co-catalyst. (C) 2011 Elsevier Ltd. All rights reserved.
• 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：——