8-chloro-6-trifluoromethyltetrazolo[1,5-a]pyridine | 242815-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 8-chloro-6-trifluoromethyltetrazolo[1,5-a]pyridine
• 英文别名: 8-Chloro-6-(trifluoromethyl)[1,2,3,4]tetraazolo[1,5-a]pyridine；8-chloro-6-(trifluoromethyl)tetrazolo[1,5-a]pyridine
• CAS: 242815-92-5
• 化学式: C₆H₂ClF₃N₄
• 分子量: 222.557
• InChiKey: UWNJTVLMYLXZPU-UHFFFAOYSA-N

物化性质

• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-chloro-6-trifluoromethyltetrazolo[1,5-a]pyridine 以 三氟乙酸 为溶剂， 生成 2-Azido-3-chloro-5-(trifluoromethyl)pyridine
  参考文献：
  名称：

  1H,13C and15N NMR and IR studies of halogen-substituted tetrazolo[1,5-a]pyridines

  摘要：

  The tetrazole-azide tautomerization of some halogen-substituted tetrazolo[1,5-a]pyridines was examined by IR spectroscopy at ambient temperature and by H-1,C-13 and N-15 NMR spectroscopy at various temperatures. The tetrazolopyridines can exhibit equilibrium between the azide and the tetrazole forms. For some of them slow exchange occurs on the NMR time-scale, such that it is possible to estimate equilibrium constants. The position and nature of the substituent in the pyridine ring result in stabilization or destabilization of the tetrazole form and exert a strong influence on the values found for the equilibrium constants. A saturation transfer experiment was carried out for 5-bromotetrazolo[1,5-a]pyridine and the rate constants were estimated. Moreover, based on the van't Hoff equation, the enthalpy Delta H degrees and entropy Delta S degrees for the tautomerization were calculated. Ab initio calculated energies and charge distribution are in good agreement with differences observed in the tetrazole-azide equilibrium constants. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199906)12:6<470::aid-poc151>3.0.co;2-u
• 作为产物：
  描述：

  2,3-二氯-5-三氟甲基吡啶 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 生成 8-chloro-6-trifluoromethyltetrazolo[1,5-a]pyridine
  参考文献：
  名称：

  1,3-二氮杂pine的合成和环收缩为氰基吡咯。

  摘要：

  几个四唑并[1,5-a]吡啶/ 2-叠氮基吡啶在低温氩气中经历光化学氮消除和环扩展为1,3-二氮杂环庚-1,2,4,6-四烯以及环裂解为氰基乙烯基酮亚胺。矩阵。6,8-二氯四唑并[1,5-a]吡啶/ 2-叠氮基-3,5-二氯吡啶易于将位置8（3）上的氯与ROH / RONa交换。8-氯-6-三氟甲基四唑并[1,5-a]吡啶经历CF（3）基团的溶剂分解，得到8-氯-6-甲氧基羰基四唑并[1,5-a]吡啶。在醇或胺存在下光解时，几种四唑并吡啶/ 2-叠氮基吡啶可提供高产率的1H-或5H-1,3-二氮杂pine。5-氯四唑并[1,5-a]吡啶/ 2-叠氮基-6-氯吡啶并分别重排为1H-和3H-3-氰基吡咯并。通过（15）N-标记研究了这种重排的机制，该机制是通过短暂的1,3-二氮杂s发生的。6,8-二氯四唑并[1,5-a]吡啶，6-氯-8-乙氧基四唑并[1,5-a]吡啶，二吡咯基甲烷和2-异丙氧

  DOI：

  10.1039/b311247k

文献信息

• Synthesis of Tetrazolo[1,5-<i>a</i>]pyridines Utilizing Trimethylsilyl Azide and Tetrabutylammonium Fluoride Hydrate
  作者：Gregory Cuny、Joydev Laha

  DOI：10.1055/s-0028-1083233

  日期：2008.12

  A method for the preparation of tetrazolo[1,5- A]pyridines from 2-halopyridines,utilizing trimethylsilyl azide in the presence of tetrabutylammoniumfluoride hydrate, is described. In addition, 8-bromotetrazolo[1,5- A]pyridine is further transformed intoa variety of novel tetrazolo[1,5- A]pyridinederivatives.

  描述了一种在四丁基氟化铵水合物存在下利用叠氮化三甲基甲硅烷从 2-卤代吡啶制备四唑并[1,5-A]吡啶的方法。此外，8-溴四唑并[1,5-A]吡啶进一步转化为多种新型四唑[1,5-A]吡啶衍生物。
• Synthesis of 1,3-diazepines and ring contraction to cyanopyrrolesDiazepines. Part 2. For Part 1 see ref. 1.Electronic supplementary information (ESI) available: drawings of the crystal structures of compounds 6T and 9Tb (ORTEP); bond lengths and angles for compounds 6T, 9Tb, 25h and 28, and 15N NMR spectra of 21, 30, 27 and 37. See http://www.rsc.org/suppdata/ob/b3/b311247k/
  作者：Ales Reisinger、Paul V. Bernhardt、Curt Wentrup

  DOI：10.1039/b311247k

  日期：——

  Several tetrazolo[1,5-a]pyridines/2-azidopyridines undergo photochemical nitrogen elimination and ring expansion to 1,3-diazacyclohepta-1,2,4,6-tetraenes, as well as ring cleavage to cyanovinylketenimines, in low temperature Ar matrices. 6,8-Dichlorotetrazolo[1,5-a]pyridine/2-azido-3,5-dichloropridine undergoes ready exchange of the chlorine in position 8 (3) with ROH/RONa. 8-Chloro-6-trifluoromethyltetrazolo[1

  几个四唑并[1,5-a]吡啶/ 2-叠氮基吡啶在低温氩气中经历光化学氮消除和环扩展为1,3-二氮杂环庚-1,2,4,6-四烯以及环裂解为氰基乙烯基酮亚胺。矩阵。6,8-二氯四唑并[1,5-a]吡啶/ 2-叠氮基-3,5-二氯吡啶易于将位置8（3）上的氯与ROH / RONa交换。8-氯-6-三氟甲基四唑并[1,5-a]吡啶经历CF（3）基团的溶剂分解，得到8-氯-6-甲氧基羰基四唑并[1,5-a]吡啶。在醇或胺存在下光解时，几种四唑并吡啶/ 2-叠氮基吡啶可提供高产率的1H-或5H-1,3-二氮杂pine。5-氯四唑并[1,5-a]吡啶/ 2-叠氮基-6-氯吡啶并分别重排为1H-和3H-3-氰基吡咯并。通过（15）N-标记研究了这种重排的机制，该机制是通过短暂的1,3-二氮杂s发生的。6,8-二氯四唑并[1,5-a]吡啶，6-氯-8-乙氧基四唑并[1,5-a]吡啶，二吡咯基甲烷和2-异丙氧
• 1H,13C and15N NMR and IR studies of halogen-substituted tetrazolo[1,5-a]pyridines
  作者：P. Cmoch、H. Korczak、L. Stefaniak、G. A. Webb

  DOI：10.1002/(sici)1099-1395(199906)12:6<470::aid-poc151>3.0.co;2-u

  日期：1999.6

  The tetrazole-azide tautomerization of some halogen-substituted tetrazolo[1,5-a]pyridines was examined by IR spectroscopy at ambient temperature and by H-1,C-13 and N-15 NMR spectroscopy at various temperatures. The tetrazolopyridines can exhibit equilibrium between the azide and the tetrazole forms. For some of them slow exchange occurs on the NMR time-scale, such that it is possible to estimate equilibrium constants. The position and nature of the substituent in the pyridine ring result in stabilization or destabilization of the tetrazole form and exert a strong influence on the values found for the equilibrium constants. A saturation transfer experiment was carried out for 5-bromotetrazolo[1,5-a]pyridine and the rate constants were estimated. Moreover, based on the van't Hoff equation, the enthalpy Delta H degrees and entropy Delta S degrees for the tautomerization were calculated. Ab initio calculated energies and charge distribution are in good agreement with differences observed in the tetrazole-azide equilibrium constants. Copyright (C) 1999 John Wiley & Sons, Ltd.