(3S,7R,7aR)-7a-Methyl-3-phenyl-7-pyrrolidin-1-yl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,7R,7aR)-7a-Methyl-3-phenyl-7-pyrrolidin-1-yl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
• 英文别名: (3S,7R,7aR)-7a-methyl-3-phenyl-7-pyrrolidin-1-yl-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: XNDCPEFRBYNESF-BFYDXBDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,7R,7aR)-7a-Methyl-3-phenyl-7-pyrrolidin-1-yl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,6S,7R,7aR)-6,7a-Dimethyl-3-phenyl-7-pyrrolidin-1-yl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one 、 (3S,6R,7R,7aR)-6,7a-Dimethyl-3-phenyl-7-pyrrolidin-1-yl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
  参考文献：
  名称：

  Asymmetric Conjugate Additions to Chiral Bicyclic Lactams. A Stereoselective General Synthesis of Chiral 3-Aminopyrrolidines

  摘要：

  Stereoselective, conjugate additions of primary amines to chiral bicyclic lactams are described. Typical yields ranged from 80% to 90% with facial diastereoselectivities ranging from 95:5 to >98:2. Several optically pure amino bicyclic lactams were transformed by reductive cleavage, in two steps, to chiral 3-aminopyrrolidines.

  DOI：

  10.1021/jo00115a040
• 作为产物：
  描述：

  四氢吡咯 、 (3S-顺)-(+)-2,3-二氢-7a-甲基-3-苯基吡咯-[2,1-b]噁唑-5(7aH)-酮 在 水 作用下， 反应 12.0h， 以89%的产率得到(3S,7R,7aR)-7a-Methyl-3-phenyl-7-pyrrolidin-1-yl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
  参考文献：
  名称：

  Asymmetric Conjugate Additions to Chiral Bicyclic Lactams. A Stereoselective General Synthesis of Chiral 3-Aminopyrrolidines

  摘要：

  Stereoselective, conjugate additions of primary amines to chiral bicyclic lactams are described. Typical yields ranged from 80% to 90% with facial diastereoselectivities ranging from 95:5 to >98:2. Several optically pure amino bicyclic lactams were transformed by reductive cleavage, in two steps, to chiral 3-aminopyrrolidines.

  DOI：

  10.1021/jo00115a040

文献信息

• Asymmetric Conjugate Additions to Chiral Bicyclic Lactams. A Stereoselective General Synthesis of Chiral 3-Aminopyrrolidines
  作者：C. J. Andres、P. H. Lee、T. H. Nguyen、A. I. Meyers

  DOI：10.1021/jo00115a040

  日期：1995.5

  Stereoselective, conjugate additions of primary amines to chiral bicyclic lactams are described. Typical yields ranged from 80% to 90% with facial diastereoselectivities ranging from 95:5 to >98:2. Several optically pure amino bicyclic lactams were transformed by reductive cleavage, in two steps, to chiral 3-aminopyrrolidines.