6-Hydroxy-3,3,5,5-tetramethyl-6-phenyl-piperidin-2-one | 97118-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 6-Hydroxy-3,3,5,5-tetramethyl-6-phenyl-piperidin-2-one
• 英文别名: 6-Hydroxy-3,3,5,5-tetramethyl-6-phenylpiperidin-2-one
• CAS: 97118-96-2
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: SIJYCQYNAOZQTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯基锂 、 3,3,5,5-四甲基哌啶-2,6-二酮 以 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到6-Hydroxy-3,3,5,5-tetramethyl-6-phenyl-piperidin-2-one
  参考文献：
  名称：

  Conformation-Related Reaction Efficiency of Glutarimides with Phenyllithium. Structures of 3,3,5,5-Tetramethylglutarimide and 2-Hydroxy-2-phenyl-3,3,5,5-tetramethyl-6-piperidone. X-ray and Theoretical Study

  摘要：

  通过 X 射线结构方法确定了 3,3,5,5-四甲基戊二酰亚胺[3,3,5,5-四甲基氮杂环己烷-2,6-二酮](8) 及其与苯锂反应的产物 2-羟基-2-苯基-3,3,5,5-四甲基-6-哌啶酮(9) 的晶体结构[(8)，单斜，P21/c，a = 7.715 (2), b = 11.136 (2), c = 11.707 (2) Å, \beta = 105.63 (3)°; (9), triclinic, P\overline 1, a = 6.1685 (6), b = 11.1475 (10), c = 11.526 (2) Å, \alpha = 117.100 (10), \beta = 103.390 (10), \gamma = 91.288 (7)°].讨论了三种不同戊二酰亚胺的分子结构。利用 ab initio 计算确定了它们的最佳能量结构。晶体学和理论研究的结果表明，甲基取代戊二酰亚胺引起的构象变化导致了电子电荷分布的变化。这些电荷分布的差异是戊二酰亚胺与苯锂反应的产率发生变化的原因。

  DOI：

  10.1107/s0108768197004874

文献信息

• Czarnocki, Zbigniew; Wrobel, Jerzy T., Bulletin of the Polish Academy of Sciences: Chemistry, 1984, vol. 32, # 9-10, p. 335 - 338
  作者：Czarnocki, Zbigniew、Wrobel, Jerzy T.

  DOI：——

  日期：——
• CZARNOCKI, Z.;WROBEL, J. T., BULL. POL. ACAD. SCI.: CHEM., 1984, 32, N 9-10, 335-338
  作者：CZARNOCKI, Z.、WROBEL, J. T.

  DOI：——

  日期：——
• Conformation-Related Reaction Efficiency of Glutarimides with Phenyllithium. Structures of 3,3,5,5-Tetramethylglutarimide and 2-Hydroxy-2-phenyl-3,3,5,5-tetramethyl-6-piperidone. X-ray and Theoretical Study
  作者：J. K. Maurin、Z. Czarnocki、B. Paluchowska、M. Winnicka-Maurin

  DOI：10.1107/s0108768197004874

  日期：1997.8.1

  Crystal structures of 3,3,5,5-tetramethylglutarimide [3,3,5,5-tetramethylazacyclohexane-2,6-dione] (8) and the product of its reaction with phenyllithium, 2-hydroxy-2-phenyl-3,3,5,5-tetramethyl-6-piperidone (9), have been determined by X-ray structural methods [(8), monoclinic, P2₁/c, a = 7.715 (2), b = 11.136 (2), c = 11.707 (2) Å, \beta = 105.63 (3)°; (9), triclinic, P\overline 1, a = 6.1685 (6), b = 11.1475 (10), c = 11.526 (2) Å, \alpha = 117.100 (10), \beta = 103.390(10), \gamma = 91.288 (7)°]. Molecular structures of three different glutarimides are discussed. Their energy optimal structures were determined with the use of ab initio calculations. The results of crystallographic and theoretical studies show that the conformational changes in glutarimide introduced by substitution with methyl groups resulted in electron-charge distribution changes. These differences in charge distribution are the reason for the observed variation in yields of the reaction of glutarimides with phenyllithium.

  通过 X 射线结构方法确定了 3,3,5,5-四甲基戊二酰亚胺[3,3,5,5-四甲基氮杂环己烷-2,6-二酮](8) 及其与苯锂反应的产物 2-羟基-2-苯基-3,3,5,5-四甲基-6-哌啶酮(9) 的晶体结构[(8)，单斜，P21/c，a = 7.715 (2), b = 11.136 (2), c = 11.707 (2) Å, \beta = 105.63 (3)°; (9), triclinic, P\overline 1, a = 6.1685 (6), b = 11.1475 (10), c = 11.526 (2) Å, \alpha = 117.100 (10), \beta = 103.390 (10), \gamma = 91.288 (7)°].讨论了三种不同戊二酰亚胺的分子结构。利用 ab initio 计算确定了它们的最佳能量结构。晶体学和理论研究的结果表明，甲基取代戊二酰亚胺引起的构象变化导致了电子电荷分布的变化。这些电荷分布的差异是戊二酰亚胺与苯锂反应的产率发生变化的原因。