1-methyl-cis-decahydro-quinolin-5-ol | 497105-61-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-methyl-cis-decahydro-quinolin-5-ol
• 英文别名: N-Methyl-5α-hydroxy-cis-decahydro-chinolin；(4aS,5R,8aS)-1-methyl-3,4,4a,5,6,7,8,8a-octahydro-2H-quinolin-5-ol
• CAS: 497105-61-0
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: LDKUXLCCTBICIL-LPEHRKFASA-N

物化性质

• 熔点：
  76-78 °C(Solv: water (7732-18-5))
• 沸点：
  266.9±13.0 °C(Predicted)
• 密度：
  1.016±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-cis-decahydro-quinolin-5-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到1-methyl-octahydroquinolin-5-one
  参考文献：
  名称：

  Control of the Conformational Equilibria in Aza-cis-Decalins:  Structural Modification, Solvation, and Metal Chelation

  摘要：

  A series of amino alcohol- and diamino-cis-decalins were synthesized and their conformational properties investigated. The equilibrium distributions of the conformational isomers were measured via NMR spectroscopy. The equilibrium ratios depend on the position of the substituents on the decalin ring system and the solvent. The 7-substituted 1-aza-cis-decalins are more likely to adopt the N-in form than the 5-substituted analogues. The N-in form is generally favored in nonpolar solvents, while the N-out form is favored in polar solvents. Complexation with LiClO4 and Et2Zn alters the equilibrium to favor the N-in decalin conformer. Both conformers coordinate lithium ions such that "on/off" conformational switching is not observed for these decalins. Comparison of the results with complexation studies of (-)-sparteine allows the criteria for an ideal "on/off" conformational switch to be defined.

  DOI：

  10.1021/jo025544t
• 作为产物：
  描述：

  3-氨基-2-环己烯-1-酮 在 palladium on activated charcoal 、 Rh/Al₂O₃ 盐酸 、 sodium hydroxide 、 氢气 、 sodium cyanoborohydride 、 乙酰氯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 20.0~100.0 ℃ 、7.58 MPa 条件下， 反应 64.0h， 生成 1-methyl-cis-decahydro-quinolin-5-ol
  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