N-亚硝基-4-哌啶酮 | 55556-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: N-亚硝基-4-哌啶酮
• 中文别名: 1-亚硝基-4-哌啶酮
• 英文名称: N-nitroso-4-piperidone
• 英文别名: N-Nitroso-4-piperidon；1-nitroso-piperidin-4-one；1-Nitroso-piperidin-4-on；Nitroso-4-piperidone；1-nitrosopiperidin-4-one
• CAS: 55556-91-7
• 化学式: C₅H₈N₂O₂
• 分子量: 128.131
• InChiKey: ADLADNOVIJYIMA-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62℃
• 沸点：
  237.54°C (rough estimate)
• 密度：
  1.2864 (rough estimate)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-亚硝基-4-哌啶酮 、 7-异丙基靛红 、 肌氨酸 以 甲醇 为溶剂， 反应 10.0h， 以38%的产率得到
  参考文献：
  名称：

  Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines

  摘要：

  One-pot three-component domino reactions of cyclic mono ketones, isatin and sarcosine/phenylglycine furnishing highly functionalised dispiropyrrolidines in moderate yields are described. The reaction when performed with cyclic amino acid, proline resulted in the dimerization of azomethine ylides. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among thirty eight compounds screened, 1-methyl-pyrrolo(spiro[2.3']-5-bromooxindole)spiro[3.2"]-1"- nitrosotetrahydro-4"(1H)-pyridinone (4t) was found to be the most active with MIC of 1.98 mu M against MTB and was 3.86 and 25.64 times more potent than the standard first line TB drugs, ethambutol and pyrazinamide respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.044
• 作为产物：
  描述：

  4-哌啶酮 生成 N-亚硝基-4-哌啶酮
  参考文献：
  名称：

  Smith, John R. Lindsay; Nee, Michael W.; Noar, J. Barry, Journal of the Chemical Society. Perkin transactions II, 1984, # 2, p. 255 - 260

  摘要：

  DOI：

文献信息

• A Comparison of the Thermal Decomposition of Nitramines and Difluoramines
  作者：J. C. Oxley、J. L. Smith、J. Zhang、C. Bedford

  DOI：10.1021/jp002516a

  日期：2001.1.1

  energies among the compounds is small. Geminal bis(difluoramino) compounds appeared to be somewhat more stable than the corresponding gem-dinitro compounds though they released more heat during decomposition. Where a nitramine functionality was present, the nitroso analogue was observed as a major decomposition product. The decomposition of gem-bis(difluoramino) and gem-dinitro compounds exhibited similarities

  比较了多个硝基和二氟氨基取代的六元环的分解速率和产物分布：硝基环己烷（I）；1,1-二硝基环己烷 (II)；1,1,4,4-四硝基环己烷(III)，1,1,4,4-四(二氟氨基)环己烷(IV)；1,4-二硝基哌嗪 (V)；1,4,4-三硝基哌啶 (VI) 和 4,4-双(二氟氨基)-1-硝基哌啶 (VII)。研究表明分解敏感性的顺序如下： N-NO2 > C-(NO2)2 > C-(NF2)2 化合物之间的键能差异很小。偕二（二氟氨基）化合物似乎比相应的偕二硝基化合物更稳定，尽管它们在分解过程中释放出更多的热量。在存在硝胺官能团的情况下，亚硝基类似物被观察为主要分解产物。偕二（二氟氨基）和偕二硝基化合物的分解表现出相似之处。两者都经历了一个双子 NX2 组的损失，然后重新排列了剩余的 ...
• STUDIES IN PIPERIDONE CHEMISTRY. I. A SYNTHESIS OF 5-HOMOPIPERAZINONES
  作者：S. C. DICKERMAN、H. G. LINDWALL

  DOI：10.1021/jo01156a005

  日期：1949.7
• Novel three-component tandem reactions of cyclic mono ketones, isatin and sarcosine: formation of dispiropyrrolidines
  作者：Raju Suresh Kumar、Subbu Perumal

  DOI：10.1016/j.tetlet.2007.07.197

  日期：2007.10

  One-pot, three-component tandem reactions of cyclic mono ketones, isatin and sarcosine affording dispiropyrrolidines stereo selectively are reported for the first time. (c) 2007 Elsevier Ltd. All rights reserved.
• Novel three-component domino reactions of ketones, isatin and amino acids: Synthesis and discovery of antimycobacterial activity of highly functionalised novel dispiropyrrolidines
  作者：Raju Suresh Kumar、Stephen Michael Rajesh、Subbu Perumal、Debjani Banerjee、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2009.09.044

  日期：2010.1

  One-pot three-component domino reactions of cyclic mono ketones, isatin and sarcosine/phenylglycine furnishing highly functionalised dispiropyrrolidines in moderate yields are described. The reaction when performed with cyclic amino acid, proline resulted in the dimerization of azomethine ylides. These compounds have been screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) using agar dilution method. Among thirty eight compounds screened, 1-methyl-pyrrolo(spiro[2.3']-5-bromooxindole)spiro[3.2"]-1"- nitrosotetrahydro-4"(1H)-pyridinone (4t) was found to be the most active with MIC of 1.98 mu M against MTB and was 3.86 and 25.64 times more potent than the standard first line TB drugs, ethambutol and pyrazinamide respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Smith, John R. Lindsay; Nee, Michael W.; Noar, J. Barry, Journal of the Chemical Society. Perkin transactions II, 1984, # 2, p. 255 - 260
  作者：Smith, John R. Lindsay、Nee, Michael W.、Noar, J. Barry、Bruice, Thomas C.

  DOI：——

  日期：——