2-叠氮基-1-甲基-3-硝基苯 | 16714-18-4

• 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-1-甲基-3-硝基苯
• 英文名称: 6-Methyl-2-nitro-phenylazid
• 英文别名: 2-Azido-1-methyl-3-nitrobenzene
• CAS: 16714-18-4
• 化学式: C₇H₆N₄O₂
• mdl: MFCD15146823
• 分子量: 178.15
• InChiKey: OTQNEHBYBTZSIK-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2929909090

反应信息

• 作为反应物：
  描述：

  2-叠氮基-1-甲基-3-硝基苯 在 N-溴代丁二酰亚胺(NBS) 、 亚磷酸三乙酯 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 甲苯 为溶剂， 反应 20.5h， 生成 4-溴甲基苯并噁二唑
  参考文献：
  名称：

  Inhibition of nucleoside transport By new analogues of nitrobenzylthioinosine

  摘要：

  Nitrobenzylthioinosine (NBTI, 1) was systematically modified by attachment of substituents at positions C6 and N9, and also by substitution of N1 with C. These modifications were chosen to reduce the polarity of the new compounds. Incorporation of the nitro functionality into a benzoxadiazole ring system was considered first. These new nucleosides showed high affinity (1.5-10 nM) towards the nucleoside transport protein as present on human erythrocyte ghosts. Next, modification of this benzoxadiazole ring system with C, S and O in different positions produced a number of less polar nucleosides with affinity in the higher nanomolar range. Modification of N9 was achieved with different alkyl and alcohol substituents. An n-butyl substituent proved best, although all variations yielded substantial decreases in affinity. Replacement of N1 by a carbon atom in combination with a 2-Cl substituent also resulted in a relatively potent NBTI derivative (47 nM). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00544-8
• 作为产物：
  描述：

  AR-甲基-AR-硝基苯胺 生成 2-叠氮基-1-甲基-3-硝基苯
  参考文献：
  名称：

  Zincke; Schwarz, Justus Liebigs Annalen der Chemie, 1899, vol. 307, p. 43

  摘要：

  DOI：

文献信息

• The reactivity of organophosphorus compounds. Part XXX. Iminophospholes and a new synthesis of benzofurazans via intramolecular rearrangement of 1-o-nitroarylimino-1,2,5-triphenylphospholes
  作者：J. I. G. Cadogan、Robert J. Scott、Robert D. Gee、Ian Gosney

  DOI：10.1039/p19740001694

  日期：——

  1-aroylimino-1,2,5-triphenylphospholes (2; X = PhCO and p-NO2·C6H4CO), but these decomposed at this temperature to give the corresponding aryl cyanides and the phosphole oxide. The use of copper-bronze reduced the decomposition point of the dioxazolidin-2-ones sufficiently for the iminophospholes to be isolated. Base catalysed decomposition of ethyl N-(p-nitrophenylsulphonyloxy)carbamate (4) in the presence of

  已经合成了一系列的N-取代的1-亚氨基-1,2,5-三苯基磷（2）。芳基，甲磺酰基，芳基磺酰基，乙氧基羰基，苯氧基羰基和二苯基次膦酰基叠氮化物与1,2,5-三苯基膦的反应得到相应的N-取代的1-亚氨基膦[2; X = Ar，MeSO 2，ArSO 2，EtO 2 C，PhO 2 C和Ph 2 P（O）]，通过非亚硝基苯路线的收率很高。甲苯磺酰磷（2； X =甲苯磺酰基）也是通过无水氯胺-T反应制得的。与磷脂。苯甲酰叠氮化物通过分解反应，然后进行库尔修斯重排反应，而不是与相对较弱的亲核性1,2,5-三苯基磷脂反应（参见Ph 3 P）。缺电子的4-硝基苯甲酰基和2,4-二硝基苯甲酰基叠氮化物给出相应的1-芳基氨基-1,2,5-三苯基磷[2; X = C 6 H ^ 4 NO 2 - p和2,4-（NO 2）2 C ^ 6 ħ 3在6和55％的产率分别]。在铜存在下的5，7-二甲基四唑并[1，5-
• New analogs of nitrobenzylthioinosine
  申请人：Grünenthal GmbH

  公开号：EP1352910A1

  公开（公告）日：2003-10-15

  This invention relates to new analogs or derivatives of nitrobenzylthioinosine, use of these new analogs of nitrobenzylthioinosine for the treatment of pain and various other diseases as well as pharmaceuticals comprising at least on new analog of nitrobenzylthioinosine.

  这项发明涉及新的硝基苯基硫基核苷类似物或衍生物，以及利用这些新的硝基苯基硫基核苷类似物治疗疼痛和其他各种疾病，以及包含至少一种新的硝基苯基硫基核苷类似物的药品。
• Click Variations on the Synthesis of 2-Nitrophenyl-4-aryl-1,2,3-triazoles without Isolation of 2-Nitrophenyl Azides
  作者：Amélie Roux、Federico Cisnetti

  DOI：10.1055/s-0039-1691524

  日期：2020.4

  We report a series of efficient procedures to prepare 2-nitrophenyl-4-aryl-1,2,3-triazoles avoiding the isolation of potentially hazardous 2-nitrophenyl azides. An organocatalyzed azide-enolate variant allows efficient access to the target compounds while it was shown that a metal-catalyzed azide-alkyne procedure involving a preliminary ­Sonogashira coupling was feasible starting from electron-deficient aryl iodides.

  我们报告了一系列高效的程序，用于制备2-硝基苯基-4-芳基-1,2,3-三唑，避免了分离潜在危险的2-硝基苯基叠氮化物。一种有机催化的叠氮-烯醇变体允许有效地获得目标化合物，同时还表明，从电子不足的芳基碘化物出发，涉及初步Sonogashira偶联的金属催化叠氮-炔烃程序是可行的。
• Unusual group migration and C(sp3)–H activation leading to stable metallacycles in the reactions of Cp*IrS2C2B10H10 and aryl azides
  作者：Wei Zhong、Mingshi Xie、Qibai Jiang、Yizhi Li、Hong Yan

  DOI：10.1039/c2cc16943f

  日期：——

  The thermal or photochemical reactions of Cp*IrS(2)C(2)B(10)H(10) (1) and aryl azides lead to C-C coupling via C(sp(3))-H activation in 2 as well as the formation of C-S bonds and new-type SSN pincer ligands in 3-8 through ortho-substituted electron-withdrawing group migration over an aryl ring.

  Cp * IrS（2）C（2）B（10）H（10）（1）和芳基叠氮化物的热或光化学反应导致CC偶联通过C（sp（3））-H活化2通过在芳基环上邻位取代的吸电子基团迁移，在3-8中形成CS键和新型SSN钳形配体。
• Dyall,L.K., Australian Journal of Chemistry, 1975, vol. 28, p. 2147 - 2159
  作者：Dyall,L.K.

  DOI：——

  日期：——