(1'S,1''R,2R,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]cyclohexanone | 253609-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (1'S,1''R,2R,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]cyclohexanone
• 英文别名: (2R)-2-[(S)-[(3aR,6aR)-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrol-1-yl]-phenylmethyl]cyclohexan-1-one
• CAS: 253609-29-9
• 化学式: C₂₀H₂₇NO
• 分子量: 297.44
• InChiKey: PWXOIQPCGHWKDF-MJKGWSOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'S,1''R,2R,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]cyclohexanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以92%的产率得到(1R,1'S,1''R,2R,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-ylmethyl)methyl]cyclohexanol
  参考文献：
  名称：

  Highly stereoselective synthesis of 1,3-aminoalcohols via Mannich reactions

  摘要：

  Diastereoselective synthesis of beta-amino ketones by a one-pot Mannich reaction and their subsequent reduction afforded sterically congested enantiomerically pure 1,3-aminoalcohols in high diastereoselectivity: dr up to >98:<2 over two steps. The absolute configurations of the newly created stereogenic centers were assigned by NMR spectroscopy and chemical correlation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00342-0
• 作为产物：
  描述：

  (3aR,6aR)-1-Trimethylsilanyl-octahydro-cyclopenta[b]pyrrole 在 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 (1'S,1''R,2R,5''R)-2-[phenyl-1'-(2''-azabicyclo[3.3.0]octane-2''-yl)methyl]cyclohexanone
  参考文献：
  名称：

  Highly stereoselective synthesis of 1,3-aminoalcohols via Mannich reactions

  摘要：

  Diastereoselective synthesis of beta-amino ketones by a one-pot Mannich reaction and their subsequent reduction afforded sterically congested enantiomerically pure 1,3-aminoalcohols in high diastereoselectivity: dr up to >98:<2 over two steps. The absolute configurations of the newly created stereogenic centers were assigned by NMR spectroscopy and chemical correlation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00342-0