3,3,5,5-Tetramethyl-cis-2,6-diphenylpiperidin-4-one

• 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: 3,3,5,5-Tetramethyl-cis-2,6-diphenylpiperidin-4-one
• 英文别名: 3,3,5,5-Tetramethyl-r-2,c-6-diphenylpiperidin-4-one；(2S,6R)-3,3,5,5-tetramethyl-2,6-diphenylpiperidin-4-one
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: IPBNOHFPIPIHRF-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3,5,5-Tetramethyl-cis-2,6-diphenylpiperidin-4-one 在 盐酸 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以75%的产率得到N-Nitroso-3,3,5,5-tetramethyl-cis-2,6-diphenylpiperidin-4-one
  参考文献：
  名称：

  Conformational Study of N-Nitroso-2,6-diphenylpiperidines and N-Nitroso-2,6-diphenylpiperidin-4-ones by Molecular Mechanics Calculations, X-ray Crystallography, and 1H and 13C NMR Spectroscopy

  摘要：

  Molecular geometries of several N-nitroso-2,6-diphenylpiperidines and N-nitroso-2,6-diphenylpiperidin-4-ones were calculated by the molecular mechanics (MM2) method with added parameters for the N-nitroso group and by X-ray crystallography and H-1 and C-13 NMR. We found that these molecules adopt either a chair conformation with two phenyl groups at the axial positions or a distorted boat-like conformation. Contrary to the earlier literature suggestions, a diequatorial chair conformer is destabilized by the A((1,3)) Strain resulting from a steric interference of the planar NNO moiety with the neighboring equatorial substituents. The X-ray crystal structures showed diaxial orientation of the phenyls in two compounds, assuming the chair conformations and boat-like piperidine ring geometry in three other nitrosamines. The H-1 and C-13 NMR spectra exhibited similar conformational preferences in solution to that predicted by the MM2 calculations. Most of the compounds derived from the symmetrically substituted amines appeared to be almost conformationally homogeneous, whereas the conformational equilibria of unsymmetrically substituted nitrosamines are rather complex.

  DOI：

  10.1021/jo00128a011
• 作为产物：
  描述：

  苯甲醛 、 2,4-二甲基-3-戊酮 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以19%的产率得到3,3,5,5-Tetramethyl-cis-2,6-diphenylpiperidin-4-one
  参考文献：
  名称：

  Conformational Study of N-Nitroso-2,6-diphenylpiperidines and N-Nitroso-2,6-diphenylpiperidin-4-ones by Molecular Mechanics Calculations, X-ray Crystallography, and 1H and 13C NMR Spectroscopy

  摘要：

  Molecular geometries of several N-nitroso-2,6-diphenylpiperidines and N-nitroso-2,6-diphenylpiperidin-4-ones were calculated by the molecular mechanics (MM2) method with added parameters for the N-nitroso group and by X-ray crystallography and H-1 and C-13 NMR. We found that these molecules adopt either a chair conformation with two phenyl groups at the axial positions or a distorted boat-like conformation. Contrary to the earlier literature suggestions, a diequatorial chair conformer is destabilized by the A((1,3)) Strain resulting from a steric interference of the planar NNO moiety with the neighboring equatorial substituents. The X-ray crystal structures showed diaxial orientation of the phenyls in two compounds, assuming the chair conformations and boat-like piperidine ring geometry in three other nitrosamines. The H-1 and C-13 NMR spectra exhibited similar conformational preferences in solution to that predicted by the MM2 calculations. Most of the compounds derived from the symmetrically substituted amines appeared to be almost conformationally homogeneous, whereas the conformational equilibria of unsymmetrically substituted nitrosamines are rather complex.

  DOI：

  10.1021/jo00128a011

文献信息

• Conformational Study of N-Nitroso-2,6-diphenylpiperidines and N-Nitroso-2,6-diphenylpiperidin-4-ones by Molecular Mechanics Calculations, X-ray Crystallography, and 1H and 13C NMR Spectroscopy
  作者：Maria Gdaniec、Maria J. Milewska、Tadeusz Po-lonski

  DOI：10.1021/jo00128a011

  日期：1995.11

  Molecular geometries of several N-nitroso-2,6-diphenylpiperidines and N-nitroso-2,6-diphenylpiperidin-4-ones were calculated by the molecular mechanics (MM2) method with added parameters for the N-nitroso group and by X-ray crystallography and H-1 and C-13 NMR. We found that these molecules adopt either a chair conformation with two phenyl groups at the axial positions or a distorted boat-like conformation. Contrary to the earlier literature suggestions, a diequatorial chair conformer is destabilized by the A((1,3)) Strain resulting from a steric interference of the planar NNO moiety with the neighboring equatorial substituents. The X-ray crystal structures showed diaxial orientation of the phenyls in two compounds, assuming the chair conformations and boat-like piperidine ring geometry in three other nitrosamines. The H-1 and C-13 NMR spectra exhibited similar conformational preferences in solution to that predicted by the MM2 calculations. Most of the compounds derived from the symmetrically substituted amines appeared to be almost conformationally homogeneous, whereas the conformational equilibria of unsymmetrically substituted nitrosamines are rather complex.