r-2,c-6-Bis(4-chlorophenyl)-c-3,t-3-dimethylpiperidin-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: r-2,c-6-Bis(4-chlorophenyl)-c-3,t-3-dimethylpiperidin-4-one
• 英文别名: (2R,6R)-2,6-bis(4-chlorophenyl)-3,3-dimethylpiperidin-4-one
• 化学式: C₁₉H₁₉Cl₂NO
• 分子量: 348.272
• InChiKey: NNZQNGKTUYDPHE-SJLPKXTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  异烟肼 、 r-2,c-6-Bis(4-chlorophenyl)-c-3,t-3-dimethylpiperidin-4-one 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以94%的产率得到(4E)-3,3-dimethyl-2r,6c-bis(p-chlorophenyl)piperidin-4-one isonicotinylhydrazone
  参考文献：
  名称：

  2,6-diarylpiperidin-4-one 腙的 X 射线衍射和核磁共振谱的构象分析

  摘要：

  摘要 由 3t-烷基-2r,6c-diarylpiperidin-4-ones 与异烟肼 (INH) 缩合得到的一系列新的 3t-烷基-2r,6c-diarylpiperidin-4-one N-异烟酰腙 (12-22) 是报道。新合成的化合物已通过元素分析、IR、1H、13C 和 2D NMR 光谱分析进行了表征。此外，3,3-二甲基-2r,6c-diarylpiperidin-4-one N-异烟酰腙的代表性晶体结构已通过 X 射线衍射分析确定。核磁共振数据显示，在所有情况下都形成了两种几何异构体（E 和 Z），并且哌啶环采用椅子构象。而在固态下，化合物在 CN 键周围具有 E 构型。这些结论也得到了化合物 16 的 X 射线数据的证实。

  DOI：

  10.1016/j.molstruc.2014.10.015
• 作为产物：
  描述：

  在 氨 作用下， 以 水 、 丙酮 为溶剂， 生成 r-2,c-6-Bis(4-chlorophenyl)-c-3,t-3-dimethylpiperidin-4-one
  参考文献：
  名称：

  NMR spectral study of some 2r,6c-diarylpiperidin-4-one (3′-hydroxy-2′-naphthoyl)hydrazones with special reference to γ-syn effect

  摘要：

  H-1 and C-13 NMR spectra have been recorded for 2r,6c-diarylpiperidin-4-one (3'-hydroxy-2'-naphthoyl)hydrazones 10-17 and 3,3-dimethyl-2r,6c-bis(p-methoxyphenyl)piperidin-4-one (5). For selected compounds 20 NMR spectra have been recorded. The spectral data along with those reported for related compounds are used to study the effect of a heteroatom X on the C-13 chemical shift of a gamma-carbon with X C-alpha C-beta C-gamma torsional angle close to 0 degrees, termed as gamma-syn effect. Also gamma-gauche and delta-effects of the alkyl groups at C-3 on the carbons of the aryl group at C-2 have been studied. The chemical shifts for the naphthalene ring are in accord with the mesomeric and steric effects of the carbonyl and hydroxy groups. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.09.015

文献信息

• Synthesis and physicochemical studies of some novel picrate derivatives
  作者：Jayaraman Jayabharathi、Venugopal Thanikachalam、Manoharan Padmavathy、Natesan Srinivasan

  DOI：10.1016/j.saa.2011.06.026

  日期：2011.10

  1H and 13C NMR spectra were recorded for some novel picrate derivatives derived from some 3,3-methyl-2,6-diarylpiperidin-4-ones and 3-benzyl-2,6-diarylpiperidin-4-one. The difference in the chemical shift of equatorial methylene proton and axial methylene proton at C(5) [Δ = δeq − δax] is highly negative which is in contrast to the value observed in the corresponding parent piperidin-4-ones and this

  记录了衍生自一些3,3-甲基-2,6-二芳基哌啶-4-酮和3-苄基-2,6-二芳基哌啶-4-酮的一些新颖的苦味酸酯衍生物的1 H和13 C NMR光谱。在的化学位移的差异赤道亚甲基质子和轴向亚甲基质子在C（5）[ Δ  =  δ当量 -  δ斧]是高度负其是与在相应的亲本中观察到的值哌啶-4-酮和这归因于syn在C-5处，轴向N–H键与轴向氢之间的1,3-双轴相互作用。详细研究了质子化对化学位移的影响。杂环质子的化学位移受苦味酸根阴离子的影响。详细研究了苦味剂的溶剂变色现象。进行DFT计算是为了找出NBO分析，HOMO-LUMO能量，MEP研究和超极化行为。从理论上研究了所研究分子的电偶极矩（μ）和第一超极化率（β）值，发现合成的分子具有非零值的微观非线性光学（NLO）行为。
• NMR spectral study of some 2r,6c-diarylpiperidin-4-one (3′-hydroxy-2′-naphthoyl)hydrazones with special reference to γ-syn effect
  作者：S. Sylvestre、K. Pandiarajan

  DOI：10.1016/j.saa.2010.09.015

  日期：2011.1

  H-1 and C-13 NMR spectra have been recorded for 2r,6c-diarylpiperidin-4-one (3'-hydroxy-2'-naphthoyl)hydrazones 10-17 and 3,3-dimethyl-2r,6c-bis(p-methoxyphenyl)piperidin-4-one (5). For selected compounds 20 NMR spectra have been recorded. The spectral data along with those reported for related compounds are used to study the effect of a heteroatom X on the C-13 chemical shift of a gamma-carbon with X C-alpha C-beta C-gamma torsional angle close to 0 degrees, termed as gamma-syn effect. Also gamma-gauche and delta-effects of the alkyl groups at C-3 on the carbons of the aryl group at C-2 have been studied. The chemical shifts for the naphthalene ring are in accord with the mesomeric and steric effects of the carbonyl and hydroxy groups. (C) 2010 Elsevier B.V. All rights reserved.
• Conformational analysis of 2,6-diarylpiperidin-4-one hydrazones by X-ray diffraction and NMR spectroscopy
  作者：C. Sankar、S. Umamatheswari、K. Pandiarajan

  DOI：10.1016/j.molstruc.2014.10.015

  日期：2015.3

  derived from the condensation of 3t-alkyl-2r,6c-diarylpiperidin-4-ones with isoniazid (INH) is reported. Newly synthesized compounds have been characterized by using elemental analysis, IR, 1H, 13C and 2D NMR spectral analysis. Moreover, representative crystal structure of 3,3-dimethyl-2r,6c-diarylpiperidin-4-one N-isonicotinoylhydrazone has been determined by X-ray diffraction analysis. NMR data revealed

  摘要 由 3t-烷基-2r,6c-diarylpiperidin-4-ones 与异烟肼 (INH) 缩合得到的一系列新的 3t-烷基-2r,6c-diarylpiperidin-4-one N-异烟酰腙 (12-22) 是报道。新合成的化合物已通过元素分析、IR、1H、13C 和 2D NMR 光谱分析进行了表征。此外，3,3-二甲基-2r,6c-diarylpiperidin-4-one N-异烟酰腙的代表性晶体结构已通过 X 射线衍射分析确定。核磁共振数据显示，在所有情况下都形成了两种几何异构体（E 和 Z），并且哌啶环采用椅子构象。而在固态下，化合物在 CN 键周围具有 E 构型。这些结论也得到了化合物 16 的 X 射线数据的证实。