N-Nitroso-r-2,c-6-diphenylpiperidine | 67787-59-1

• 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: N-Nitroso-r-2,c-6-diphenylpiperidine
• 英文别名: 1-Nitroso-2,6-diphenylpiperidine
• CAS: 67787-59-1
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: MORPGHSBVNIXMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  r-2,c-6-二苯基哌啶 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 以57.3%的产率得到N-Nitroso-r-2,c-6-diphenylpiperidine
  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

文献信息

• FEDOTOVA O. V.; KRIVENKO A. P.; XARCHENKO V. G.; TILICHENKO M. N., CAPATOB. YH-T. CAPATOB, 1976, 7 S., BIBLIOGR. 9 NAZV. (RUKOPIS DEP. V VIN+
  作者：FEDOTOVA O. V.、 KRIVENKO A. P.、 XARCHENKO V. G.、 TILICHENKO M. N.

  DOI：——

  日期：——
• Chemistry of N-nitroso compounds. 1. Synthesis and stereodynamics of N-nitrosopiperidines and N-nitrosopiperidin-4-ones
  作者：Thiruvenkadam Ravindran、Ramasubbu Jeyaraman、Robert W. Murray、Megh Singh

  DOI：10.1021/jo00016a007

  日期：1991.8

  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.