(αS,βR)-(1-tert-butoxycarbonyl-octahydro-cyclopenta[b]pyrrol-2-yl)-1'-(4-methyl-phenyl)-methanol | 197903-57-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (αS,βR)-(1-tert-butoxycarbonyl-octahydro-cyclopenta[b]pyrrol-2-yl)-1'-(4-methyl-phenyl)-methanol
• 英文别名: tert-butyl (2R,3aR,6aR)-2-[(R)-hydroxy-(4-methylphenyl)methyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-1-carboxylate
• CAS: 197903-57-4
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: JHRXLIDAGVLWKX-BRSBDYLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (αS,βR)-(1-tert-butoxycarbonyl-octahydro-cyclopenta[b]pyrrol-2-yl)-1'-(4-methyl-phenyl)-methanol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以78%的产率得到(αS,βR)-(1-methyl-octahydro-cyclopenta[b]pyrrol-2-yl)-1'-(4-methyl-phenyl)-methanol
  参考文献：
  名称：

  Synthesis and application of new (threo)- and (erythro)-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

  摘要：

  Asymmetric catalytic ethylation of benzaldehyde utilizing a series of new, artificial B-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system is presented. A systematic investigation on the inductive correlation of up to four catalyst-internal stereogenic centers and on steric aspects of these structures has been conducted with diastereomerically pure, bicyclic (erythro)- and (threo)-compounds 2-13. Chiral ligands have been developed reaching excellent enantioselectivities, e.g. enantiomeric excesses up to 91% with a favored (R)-induction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00327-3