1-methyl-octahydroquinolin-5-one | 1874-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: 1-methyl-octahydroquinolin-5-one
• 英文别名: rel-(4aR,8aR)-Octahydro-1-methyl-5(1H)-quinolinone；(4aS,8aS)-1-methyl-2,3,4,4a,6,7,8,8a-octahydroquinolin-5-one
• CAS: 1874-94-8
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: JCDSZVGRRSAUJB-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-octahydroquinolin-5-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以85%的产率得到1-methyl-octahydroquinolin-5-one oxime
  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：

  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

文献信息

• Control of the Conformational Equilibria in Aza-<i>cis</i>-Decalins:  Structural Modification, Solvation, and Metal Chelation
  作者：Puay-Wah Phuan、Marisa C. Kozlowski

  DOI：10.1021/jo025544t

  日期：2002.9.1

  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.