(2RS,6SR)-2,6-diphenylpiperidin-4-one hydrochloride | 134848-34-3

• 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: (2RS,6SR)-2,6-diphenylpiperidin-4-one hydrochloride
• 英文别名: r-2,c-6-diphenylpiperidin-4-one hydrochloride；cis-2,6-diphenyl-piperidin-4-one; hydrochloride；cis-2,6-Diphenyl-piperidin-4-on; Hydrochlorid；(2S,6R)-2,6-diphenylpiperidin-1-ium-4-one;chloride
• CAS: 134848-34-3
• 化学式: C₁₇H₁₇NO*ClH
• 分子量: 287.789
• InChiKey: ALUVTRXIDOSUNQ-OKZTUQRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2RS,6SR)-2,6-diphenylpiperidin-4-one hydrochloride 在 sodium azide 、 硫酸 作用下， 以85%的产率得到r-2,c-7-diphenylhexahydro-1,4-diazepin-5-one
  参考文献：
  名称：

  Chemistry of N-nitroso compounds. 3. Synthesis and conformational analysis of N-nitrosohexahydro-1,4-diazepin-5-ones

  摘要：

  A comparison of the barrier to N-X rotation in a series of compounds with various N-X=Y systems has shown that the N-nitrosamines, some of which have been found to be highly carcinogenic, exhibit the highest rotation barrier. All the other systems which, to date, have not been found to be carcinogenic have lower barriers. With a view to studying the influence of the N-nitroso group on the conformations of N-nitrosodiazepinones, several 1-nitroso-r-2,c-7-diphenylhexahydro-1,4-diazepin-5-ones 16-20 were synthesized from the corresponding r-2,c-7-diphenylhexahydro-1,4-diazepin-5-ones 11-15 and their conformations in deuterated solvents were studied. The N-nitrosodiazepinones 16-20 were found to prefer boat conformations, with some flattening at the nitroso end of the ring and with quasi-axial phenyl groups. As shown earlier, N-nitroso-r-2,c-6-diphenylpiperidines prefer partially twisted chair conformations with equatorial phenyl groups and r-2,c-6-dimethyl-N-nitrosopiperidine prefers a chair conformation with 1,3-diaxial methyl groups. The title compounds 16-20 exist in conformational equilibria involving syn and anti orientations of the coplanar nitroso group in an approximate syn-anti ratio of 60:40 (observed from H-1 NMR spectroscopic studies). The C-13 NMR spectra of these compounds show that the carbons syn to the nitroso group are shifted upfield by about 11-15 ppm compared to the precursor compounds 11-15, while the anti carbons were shifted by less than 1 ppm in either direction. It was observed that all of the syn alpha-protons are more deshielded than the anti alpha-protons while for the beta-protons the reverse is true. The N-N=O rotational barriers for these compounds could not be determined precisely since they start decomposing above 150-degrees-C in DMSO-d6 Solutions. A rough estimate of the energy barrier for the isopropyl derivative 19 shows that the barrier is at least 21.5 kcal mol-1.

  DOI：

  10.1021/jo00048a041

文献信息

• Spectral characterization of novel bis heterocycles comprising both piperidine and thiohydantoin nuclei
  作者：J. Thanusu、V. Kanagarajan、M. Gopalakrishnan

  DOI：10.1007/s11164-010-0221-7

  日期：2010.12

  A series of bis heterocycles comprising both piperidine and thiohydantoin nuclei namely 3-(3-alkyl-2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones is synthesized and characterized by melting point, elemental analysis, MS, FT–IR, one-dimensional NMR (1H, D2O exchanged 1H and 13C), two-dimensional HOMOCOSY, and NOESY spectroscopic data.

  通过熔点、元素分析、质谱、傅立叶变换红外光谱、一维核磁共振（1H、D2O 交换 1H 和 13C）、二维 HOMOCOSY 和 NOESY 光谱数据，合成了一系列由哌啶和硫代海因核组成的双杂环，即 3-(3-烷基-2,6-二芳基哌啶-4-亚基)-2-硫酮咪唑烷-4-酮。
• Chemistry of N-nitroso compounds. 3. Synthesis and conformational analysis of N-nitrosohexahydro-1,4-diazepin-5-ones
  作者：Udayampalayam P. Senthilkumar、Ramasubbu Jeyaraman、Robert W. Murray、Megh Singh

  DOI：10.1021/jo00048a041

  日期：1992.10

  A comparison of the barrier to N-X rotation in a series of compounds with various N-X=Y systems has shown that the N-nitrosamines, some of which have been found to be highly carcinogenic, exhibit the highest rotation barrier. All the other systems which, to date, have not been found to be carcinogenic have lower barriers. With a view to studying the influence of the N-nitroso group on the conformations of N-nitrosodiazepinones, several 1-nitroso-r-2,c-7-diphenylhexahydro-1,4-diazepin-5-ones 16-20 were synthesized from the corresponding r-2,c-7-diphenylhexahydro-1,4-diazepin-5-ones 11-15 and their conformations in deuterated solvents were studied. The N-nitrosodiazepinones 16-20 were found to prefer boat conformations, with some flattening at the nitroso end of the ring and with quasi-axial phenyl groups. As shown earlier, N-nitroso-r-2,c-6-diphenylpiperidines prefer partially twisted chair conformations with equatorial phenyl groups and r-2,c-6-dimethyl-N-nitrosopiperidine prefers a chair conformation with 1,3-diaxial methyl groups. The title compounds 16-20 exist in conformational equilibria involving syn and anti orientations of the coplanar nitroso group in an approximate syn-anti ratio of 60:40 (observed from H-1 NMR spectroscopic studies). The C-13 NMR spectra of these compounds show that the carbons syn to the nitroso group are shifted upfield by about 11-15 ppm compared to the precursor compounds 11-15, while the anti carbons were shifted by less than 1 ppm in either direction. It was observed that all of the syn alpha-protons are more deshielded than the anti alpha-protons while for the beta-protons the reverse is true. The N-N=O rotational barriers for these compounds could not be determined precisely since they start decomposing above 150-degrees-C in DMSO-d6 Solutions. A rough estimate of the energy barrier for the isopropyl derivative 19 shows that the barrier is at least 21.5 kcal mol-1.