2-叠氮基-3-硝基苯甲醛 | 61063-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-叠氮基-3-硝基苯甲醛
• 英文名称: 2-azido-3-nitrobenzaldehyde
• 英文别名: 2-azido-3-nitro-benzaldehyde；2-Azido-3-nitrobenzaldehyd
• CAS: 61063-05-6
• 化学式: C₇H₄N₄O₃
• 分子量: 192.134
• InChiKey: WPKXRNWHHXXQSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-叠氮基-3-硝基苯甲醛 以 甲苯 为溶剂， 反应 5.0h， 生成 7-Nitro-anthranil
  参考文献：
  名称：

  Furazans and furazan oxides. 7. Interconversions of anthranils, benzofurazan oxides, and indazoles

  摘要：

  DOI：

  10.1021/jo00425a030
• 作为产物：
  描述：

  2-叠氮基-1-甲基-3-硝基苯 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.75h， 生成 2-叠氮基-3-硝基苯甲醛
  参考文献：
  名称：

  Synthesis and Voltage-Clamp Studies of Methyl 1,4-Dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylate Racemates and Enantiomers and of Their Benzofuroxanyl Analogues

  摘要：

  Racemic methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-(benzofurazanyl)pyridine-3-carboxylates(+/-)-10 and (+/-)-11 and their benzofuroxanyl analogues (+/-)-12 and (+/-)-13 were prepared using a modified Hantzsch reaction that involved the condensation of nitroacetone with methyl 3-aminocrotonate and the appropriate aldehydes. The racemic mixtures were resolved into the corresponding enantiomers. Whole-cell voltage-clamp studies on L-type Ca2+ channels expressed in a rat insulinoma cell line (RINm5F) showed that all the dextrorotatory antipodes were effective agonists of L-type Ca2+ currents, while the levorotatory ones were weak Ca2+ entry blockers. The (+)-enantiomer of benzofurazan-5'-yl derivative 11 demonstrated unusual activity in that, in addition to producing a potentiation of L-type currents, it interfered with the voltage-dependent gating of L-type channels by producing a net delay of their activation at low voltages. This compound represents an interesting tool to probe L-type Ca2+ channel structure and function.

  DOI：

  10.1021/jm980623b

文献信息

• SNAr azidation of phenolic functions utilizing diphenyl phosphorazidate
  作者：Kotaro Ishihara、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tetlet.2019.151493

  日期：2020.2

  A useful method for the synthesis of aryl azides via SNAr reaction of phenol derivatives using diphenyl phosphorazidate (DPPA) as an azidation reagent was developed. Various phenol derivatives bearing electron-withdrawing groups were converted into the corresponding aryl azides in a single step. This method is easy to perform and enables the preparation of aryl azides without the use of explosive azide

  开发了一种有用的方法，该方法通过使用叠氮磷酸二苯酯（DPPA）作为叠氮化试剂通过苯酚衍生物的SNAr反应进行芳基叠氮化物的合成。带有吸电子基团的各种酚衍生物可在一个步骤中转化为相应的芳基叠氮化物。该方法易于实施，并且能够在不使用爆炸性叠氮化物源的情况下制备芳基叠氮化物。
• Thermolysis of 4-(2-azido-3-nitrophenyl)-1,4-dihydropyridines as source of β-carboline derivatives and some related compounds
  作者：Sonja Visentin、Giuseppe Ermondi、Donatella Boschi、Giorgio Grosa、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/s0040-4039(01)00777-8

  日期：2001.7

  Thermolysis in refluxing xylene of 4-(2-azido-3-nitrophenyl)-1,4-dihydropyridines was investigated. β-Carboline derivatives and related compounds were obtained in various yields, according to the nature of the substituents in the 1,4-dihydropyridine ring.

  研究了4-（2-叠氮基-3-硝基苯基）-1,4-二氢吡啶在回流二甲苯中的热解。根据1，4-二氢吡啶环中取代基的性质，可以各种产率获得β-咔啉衍生物和相关化合物。
• Synthesis and complexing properties of macrocycles incorporating 2,2'-biindazolyl binding subunits
  作者：Juan C. Cuevas、Javier De Mendoza、Pilar Prados

  DOI：10.1021/jo00244a038

  日期：1988.4
• CUEVAS, JUAN C.;DE, MENDOZA JAVIER;PRADOS, PILAR, J. ORG. CHEM., 53,(1988) N 9, 2055-2066
  作者：CUEVAS, JUAN C.、DE, MENDOZA JAVIER、PRADOS, PILAR

  DOI：——

  日期：——
• BALASUBRAHMANYAM S. N.; RADHAKRISHNA A. S.; BOULTON A. J.; KAN-WOON T., J. ORG. CHEM. <JOCE-AH>, 1977, 42, NO 5, 897-901
  作者：BALASUBRAHMANYAM S. N.、 RADHAKRISHNA A. S.、 BOULTON A. J.、 KAN-WOON T.

  DOI：——

  日期：——