2,3,5,6-tetraphenylpiperidin-4-one | 87731-83-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3,5,6-tetraphenylpiperidin-4-one
• CAS: 87731-83-7
• 化学式: C₂₉H₂₅NO
• 分子量: 403.524
• InChiKey: CRLQJTSACHTAGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2,3,5,6-tetraphenylpiperidin-4-one 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 以72.3%的产率得到N-Nitroso-r-2,t-3,t-5,c-6-tetraphenylpiperidin-4-one
  参考文献：
  名称：

  Chemistry of N-nitroso compounds. 1. Synthesis and stereodynamics of N-nitrosopiperidines and N-nitrosopiperidin-4-ones

  摘要：

  The stereochemistry of a series of N-nitroso-r-2,c-6-diphenylpiperidin-4-ones (10-15) and N-nitroso-r-2,c-6-diphenylpiperidines (16-18) in solution has been investigated by H-1 NMR, C-13 NMR, and dynamic H-1 NMR spectroscopic studies. Unlike the r-2,c-6-dialkyl-N-nitrosopiperidines, which have diaxial alkyl groups, these N-nitroso-r-2,c-6-diphenylpiperidines (16-18) and N-nitroso-r-2,c-6-diphenylpiperidin-4-ones (10-15) have diequatorial phenyl groups even though the nitroso group is coplanar to the dynamically averaged plane of the piperidine ring. The rotamer populations of the N-NO orientations in the nitrosamines were derived from continuous wave H-1 NMR spectral data and are correlated with the steric bulk of the substituents present at the C-3 and C-5 positions. N-Nitroso-r-2,c-6-diphenylpiperidine-4-one (10) was found to have a higher rotational barrier than N-nitroso-r-2,c-6-diphenylpiperidine (16). We attribute this difference to a greater degree of coplanarity (C3-C2-N1-C6-C5) in 10 than in 16. The rotational barriers in 10 were found to decrease as the bulk of the substituents at C3 and C5 increased. The rotational barrier in N-nitroso-r-2,c-6-diphenylpiperidine (16) was found to be lower than the reported rotational barriers of N-nitroso-r-2,c-6-dimethylpiperidine and N-nitroso-2,2,6,6-tetramethylpiperidine.

  DOI：

  10.1021/jo00016a007
• 作为产物：
  描述：

  苯甲醛 、 二苄基甲酮 在 乙酸铵 作用下， 以 乙醇 为溶剂， 以64%的产率得到2,3,5,6-tetraphenylpiperidin-4-one
  参考文献：
  名称：

  2,6-二芳基-3-3,5-二苯基哌啶-4-乙酸的开环：（E）-4-芳基-1,3-二苯基但是-3-en-2-en的结构研究和Hirshfeld表面分析那些

  摘要：

  通过用乙酸处理，从2,6-二芳基-3,5-二苯基哌啶-4-中获得了六个α，β-不饱和羰基化合物。提出了2,6-二芳基-3,5-二苯基哌啶-4-酮开环的可能机理。通过1 H和13 C核磁共振（NMR）光谱研究表征了所得的（E）-4-芳基-1,3-二苯基丁-3-烯-2-酮。其中一种化合物已通过2D NMR技术进行了完全表征，并且该化合物的结构通过单晶X射线衍射（XRD）分析得到了进一步证明。讨论了两种化合物的晶体结构，晶体的三维构架和Hirshfeld表面分析。在晶体中，分子主要由C连接H···O氢键相互作用，并且该相互作用在其中一种化合物中形成具有R 2 1（6）和R 2 1（10）环基序的反相二聚体。Hirshfeld表面表示H···H接触在整个表面上的优势。

  DOI：

  10.1002/jhet.4188

文献信息

• Synthesis of Spiro[2<i>H</i>-1,3-benzoxazine-2,4′-piperidines] from<i>N</i>,<i>N</i>′-Dibenzylidenephenylmethanediamines and 2,6-Diaryl-4-piperidones
  作者：Tokiharu Takajo、Satoshi Kambe、Wataru Ando

  DOI：10.1055/s-1983-30427

  日期：——
• Crystal and molecular structure of 1-methyl-2,3,5,6-tetraphenylpiperidin-4-ol, C30H29NO
  作者：V. Parthasarathi、Paul T. Beurskens、H. J. J. Behm、S. Garcia-Granda、M. Krishna Pillay

  DOI：10.1007/bf01188189

  日期：1986.12
• Ganapathy, K.; Vijayan, B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 6, p. 614 - 616
  作者：Ganapathy, K.、Vijayan, B.

  DOI：——

  日期：——
• Iodine mediated rearrangement of tetraarylpiperidin-4-ones: Synthesis, structure analysis and biological studies of 5-aryl-2-methoxy-2,4-diphenyl-1H-pyrrole-3-ones
  作者：G. Vengatesh、M. Sundaravadivelu、S. Muthusubramanian

  DOI：10.1016/j.molstruc.2019.126980

  日期：2020.1

  An interesting iodine/methanol mediated rearrangement of tetraaylpiperidin-4-ones to 2-methoxy-2,4,5-triaryl-1H-pyrrole-3-ones is described. The structural features of the products are investigated by spectral data and single crystal X-ray analysis. The antifungal, antibacterial and antioxidant characteristics of the synthesized compounds have been studied. (C) 2019 Elsevier B.V. All rights reserved.
• GANAPATHY, K.;VIJAYAN, B., J. INDIAN CHEM. SOC., 1983, 60, N 6, 572-574
  作者：GANAPATHY, K.、VIJAYAN, B.

  DOI：——

  日期：——