t-3,t-5-Dimethyl-r-2,c-6-diphenylpiperidin-t-4-ol | 19123-20-7

• 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: t-3,t-5-Dimethyl-r-2,c-6-diphenylpiperidin-t-4-ol
• 英文别名: r(2)-trans-4-hydroxy-trans-3,5-dimethyl-cis-2,6-diphenylpiperidine；3,5-Dimethyl-2,6-diphenyl-piperidin-4-ol；3c,5c-dimethyl-2t,6t-diphenyl-piperidin-4r-ol
• CAS: 19123-20-7
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: GGCLDJYYOISOSI-PFVFBNAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  t-3,t-5-Dimethyl-r-2,c-6-diphenylpiperidin-t-4-ol 在 盐酸 、 sodium nitrite 作用下， 以 氯仿 为溶剂， 生成 N-Nitroso-t-3,t-5-dimethyl-r-2,c-6-diphenylpiperidin-t-4-ol
  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：

  aluminum isopropoxide 、 r-2,c-6-diphenyl-t-3,t-5-dimethylpiperidin-4-one 在 异丙醇 作用下， 生成 t-3,t-5-Dimethyl-r-2,c-6-diphenylpiperidin-t-4-ol
  参考文献：
  名称：

  Baliah; Ekambaram, Journal of the Indian Chemical Society, 1955, vol. 32, p. 274,276,277

  摘要：

  DOI：

文献信息

• Determination of the configuration of piperidin-4-ol silyl ethers by mass spectrometry with chemical ionization
  作者：R. S. Borisov、V. G. Zaikin、K. A. Loginova

  DOI：10.1007/s11172-006-0474-x

  日期：2006.9

  Mass spectrometry with chemical ionization (isobutane as reactant gas) can be used for the determination of the configuration of the chiral center at the C(4) atom in molecules of silyl ethers of 2,6-diaryl-substituted piperidin-4-ols.

  具有化学电离（异丁烷作为反应气体）的质谱可用于确定 2,6-二芳基取代哌啶-4-醇的甲硅烷基醚分子中 C(4) 原子处手性中心的构型。
• Conformational Studies of Somet(4)-Acetoxy-r(2),c(6)-diphenyl-N-acetylpiperidines Using1H NMR Spectra. Evidence for Contribution of Boat Forms with a Substituent in the Flagpole Position
  作者：K. Pandiarajan、A. Manimekalai、N. Kalaiselvi

  DOI：10.1002/(sici)1097-458x(199706)35:6<372::aid-omr99>3.0.co;2-l

  日期：1997.6

  The NOESY spectrum and vicinal coupling constants of t(4)‐acetoxy‐3,3‐dimethyl‐r(2),c(6)‐diphenyl‐N‐acetylpiperidine suggest that the compound adopts a chair conformation with axial phenyl groups. The vicinal coupling constants of t(4)‐acetoxy‐r(2),c(6)‐diphenyl‐N‐acetylpiperidine could be accounted for by an equilibrium mixture of the chair conformation with axial phenyl groups and a boat conformation

  t(4)-乙酰氧基-3,3-二甲基-r(2),c(6)-二苯基-N-乙酰哌啶的NOESY光谱和邻位耦合常数表明该化合物采用具有轴向苯基的椅子构象。t(4)-乙酰氧基-r(2),c(6)-二苯基-N-乙酰哌啶的邻位耦合常数可以通过带有轴向苯基的椅式构象和带有一个苯基的船形构象的平衡混合物来​​解释组在旗杆位置。邻位耦合常数表明，在 t(4)-乙酰氧基-t(3)-甲基-r(2),c(6)-二苯基-N-乙酰哌啶的情况下，另一种船构象与旗杆位置的乙酰氧基t(4)-乙酰氧基-t(3),t(5)-二甲基-r(2),c(6)-二苯基-N-乙酰哌啶主要以船形构象存在旗杆位置。之前为 N-乙酰基索索定中的哌啶环提出的扁平椅子构象已被证明是不正确的，并指定了没有烯丙基应变的船构象。还重新检查了对 N-亚硝基-2α-甲基十氢喹啉光谱结果的早期解释。© 1997 约翰威利父子公司。