7α-hydroxy-1-methyl-cis-octahydro-quinolin-2-one | 497105-88-1

• 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: 7α-hydroxy-1-methyl-cis-octahydro-quinolin-2-one
• 英文别名: (4aS,7S,8aS)-7-hydroxy-1-methyl-3,4,4a,5,6,7,8,8a-octahydroquinolin-2-one
• CAS: 497105-88-1
• 化学式: C₁₀H₁₇NO₂
• 分子量: 183.25
• InChiKey: HCABSOJFDOFKTI-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,7-Dioxo-1,2,3,4,4a,5,6,7-octahydroquinoline 在 盐酸 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 7α-hydroxy-1-methyl-cis-octahydro-quinolin-2-one
  参考文献：
  名称：

  Theoretical and Experimental Studies of Asymmetric Organozinc Additions to Benzaldehyde Catalyzed by Flexible and Constrained γ-Amino Alcohols

  摘要：

  The cis-decalin based gamma-amino alcohols, 1-5, were synthesized, resolved, and employed as catalysts in the addition of organozincs to benzaldehyde. Despite large facial differentiation in the RZn adducts of the ligands, the enantioselectivities were found to be moderate. Transition structure calculations were done using several quantum chemical methods to examine the underlying causes of the selectivity for three gamma-amino alcohols, 1, 2, and 3. The tricyclic mu-oxo (6/4/4), rather than the bicyclic six-membered (6/6), transition structures were found to explain the observed enantioselectivity for 2 and 3. MP2 calculations gave the best correlation to the experimental results compared to B3LYP and HIP calculations. The conformational flexibility of the chiral ligands was found to be an important factor in the selectivity.

  DOI：

  10.1021/jo0262210