8-氯-1,3-二甲基-5H-吡唑并[1,2-a]苯并三唑-4-内盐 | 60418-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 8-氯-1,3-二甲基-5H-吡唑并[1,2-a]苯并三唑-4-内盐
• 英文名称: 8-chloro-1,3-dimethyl-5H-pyrazolo<1,2-a>benzotriazol-4-ium inner salt
• 英文别名: 8-chloro-1,3-dimethyl-5H-benzo[d]pyrazolo[1,2-a][1,2,3]triazolylium betaine；5H-Pyrazolo[1,2-a]benzotriazol-4-ium, 8-chloro-1,3-dimethyl-, inner salt；8-chloro-1,3-dimethylpyrazolo[1,2-a]benzotriazol-4-ium-5-ide
• CAS: 60418-48-6
• 化学式: C₁₁H₁₀ClN₃
• 分子量: 219.673
• InChiKey: AODVXRCETRJYAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  8-氯-1,3-二甲基-5H-吡唑并[1,2-a]苯并三唑-4-内盐 以 苯 为溶剂， 反应 5.0h， 生成 8-chloro-2-methylpyrazoloquinoxaline 、 1-(2-amino-5-chlorophenyl)-3,5-dimethylpyrazole
  参考文献：
  名称：

  Chemistry of nitrenes generated by the photocleavage of both azides and a five-membered heterocycle

  摘要：

  Pyrazolo[1,2-a]benzotriazole and some of its derivatives (2a-c) are photochemically cleaved to form 2-(1-pyrazolyl)phenylnitrenes, which are also obtained through a more conventional path by photodecomposition of the pyrazolylphenyl azides (1a-c). Product studies and laser flash photolysis analysis of nitrenes from both sources show that there is competition between fast intramolecular reclosure to heterocycles 2 and rearrangement to dehydroazepines. The latter species are trapped by nucleophiles, or otherwise slowly rearrange back to the nitrenes (conformational factors affect these processes). The (quite unreactive) triplet nitrenes are identified spectroscopically and possibly are in equilibrium with the previous transients.

  DOI：

  10.1021/ja00018a032
• 作为产物：
  描述：

  1-(2-amino-5-chlorophenyl)-3,5-dimethylpyrazole 在 盐酸 、 sodium azide 、 芘 、 sodium acetate 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 8-氯-1,3-二甲基-5H-吡唑并[1,2-a]苯并三唑-4-内盐
  参考文献：
  名称：

  单线态和三线态氮烯的竞争环化。第8部分。1-（2-硝基苯并苯基）吡唑及相关体系

  摘要：

  已经研究了通过亚磷酸三乙酯的硝基基团脱氧或通过相应叠氮化物的热解或光解而得到的标题腈。取代基（氯，溴，青梅，NME的效果2中，Me，CF 3，和NO 2）两者间位和对位已经研究了对硝基苯的吡咯烷酮是确定为吡唑并苯并三唑或吡唑并喹喔啉的优选环化方式的决定因素。同样，已经研究了溶剂，敏化剂和淬灭剂的作用。已经定义了异构体1-和2-（2-硝基苯基）-4,5,6,7-四氢吲唑的途径，并通过研究这些产物的腈介导的环化作用对文献进行了修正。还研究了类似的1-（2-carbenophenyl）-和1-（2-nitrenosulphonylphenyl）-3,5-二甲基吡唑的化学反应，前者给出了2-（3,5-二甲基吡唑-1-基）-苯并恶嗪和-苄醇，后者则产生分子内的氮攻击（吡唑并苯并噻嗪三嗪）和分子间反应的产物。所有反应途径的合理化已经提出。

  DOI：

  10.1039/p19800000982

文献信息

• Photodecomposition of Some Para-Substituted 2-Pyrazolylphenyl Azides. Substituents Affect the Phenylnitrene S−T Gap More Than the Barrier to Ring Expansion
  作者：Angelo Albini、Gianfranco Bettinetti、Giovanna Minoli

  DOI：10.1021/ja982585r

  日期：1999.4.1

  A series of para-substituted (H, Me, Cl, F, CF3, OMe, NMe2) phenyl azides bearing a dimethylpyrazolyl group in position 2 allowing intramolecular trapping of singlet nitrene have been photolyzed at both 295 and 90 K in ethanol. For three significant models (H, CF3, NMe2), the reaction has been further studied in the presence of diethylamine (DEA) and of oxygen. With all substituents but NMe2, singlet nitrene (trapped intramolecularly to give pyrazolobenzotriazoles) and didehydroazepine (trapped with DEA to give 5H-azepines and then rearranging to 3H-azepines) are in equilibrium. With the NMe2 derivative, the nonelectrophilic singlet is not trapped, while DEA adds to the benzoazirine, the precursor of the didehydroazepine. Thus, electronic effects do not hinder the equilibrium between singlet nitrene and its cyclic isomers, while determining which of the above intermediates decays to a stable end product. The electron-donating group NMe2 has a second important effect, causing a drastic enhancement of the triplet nitrene energy and reduction of the S-T gap, so that triplet nitrene is also in equilibrium with the singlet and the benzoazirine. As for triplet nitrenes,these have been characterized in matrix at 90 K, and the competition between dimerization (to give;azo compounds, as typical of such stabilized species) and hydrogen abstraction from the solvent (involving a sizable barrier) has been studied. The energetic p-dimethylamino triplet undergoes hydrogen abstraction exclusively. When present, oxygen adds efficiently to all of the nitrenes, giving a nitroso oxide, Likewise characterized in the matrix, which then converts to the nitroso and nitro,derivatives in good yields. Photochemical excitation of the triplet in matrix leads to intramolecular hydrogen abstraction.
• Albini, Angelo; Bettinetti, Gianfranco; Minoli, Giovanna, Heterocycles, 1995, vol. 40, # 2, p. 597 - 606
  作者：Albini, Angelo、Bettinetti, Gianfranco、Minoli, Giovanna

  DOI：——

  日期：——
• LINDLEY J. M.; MCROBBIE I. M.; METH-COHN O.; SUSCHITZKY H., J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 4, 982-994
  作者：LINDLEY J. M.、 MCROBBIE I. M.、 METH-COHN O.、 SUSCHITZKY H.

  DOI：——

  日期：——