(2R,3R,3aR)-3-Diphenylphosphanyl-2,6,6-trimethyl-hexahydro-pyrrolo[1,2-b]isoxazole | 138865-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2R,3R,3aR)-3-Diphenylphosphanyl-2,6,6-trimethyl-hexahydro-pyrrolo[1,2-b]isoxazole
• CAS: 138865-96-0
• 化学式: C₂₁H₂₆NOP
• 分子量: 339.417
• InChiKey: RSVLSEIWPYINGP-AHRSYUTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 、 diphenyl((Z)-1-propenyl)phosphine 以 甲苯 为溶剂， 反应 36.0h， 以50%的产率得到(2R,3R,3aR)-3-Diphenylphosphanyl-2,6,6-trimethyl-hexahydro-pyrrolo[1,2-b]isoxazole
  参考文献：
  名称：

  Direct synthesis of isoxazolidinylphosphines by cycloaddition of nitrones to diphenylphosphinoethenes and x-ray structure of 7,7-dimethyl-1-oxo-1-phenyl-3-diphenylphosphinyl-hexahydro-1H-pyrrolo [1,2-c] [1,3,2] oxazaphosphorine

  摘要：

  The 1,3-dipolar cycloaddition reaction of N-alkyl nitrones with diphenylvinylphosphines affords directly isoxazolidinylphosphines in satisfactory yields and in regio- and stereoselective manner. The parent diphenylvinylphosphine was found to favor the formation of 5-phosphinoisoxazolidines whereas diphenylpropenylphosphine gave instead the 4-phosphinoisoxazolidine regioisomer. However, in reactions utilizing an alkylarylvinylphosphine and/or N-arylnitrone, oxidation of the phosphine by the nitrone reagent was found to precede the cycloaddition. An attempted conversion of the bicyclic isoxazolidine derived from 2,2-dimethyl-dihydro-2H-pyrrole 1-oxide and diphenylvinylphosphine to the perhydropyrrolo[1,2-c] [1,3,2]oxaza-phosphorine ring system was accomplished through the use of the corresponding phosphine oxide derivative and provided a single diastereoisomer of the desired pyrrolooxazaphosphorinane characterized ultimately in the form of its dioxide hydrate by the X-ray diffraction technique.

  DOI：

  10.1016/s0040-4020(01)86511-x