1-(2-nitrophenyl)-2-tosylhydrazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-nitrophenyl)-2-tosylhydrazine
• 英文别名: 4-methyl-N'-(2-nitrophenyl)benzenesulfonohydrazide
• 化学式: C₁₃H₁₃N₃O₄S
• 分子量: 307.33
• InChiKey: VFLSNCQYIICDOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-nitrobenzenediazonium tetrafluoroborate 在 potassium tert-butylate 、 异氰基乙酸叔丁酯 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 1-(2-nitrophenyl)-2-tosylhydrazine
  参考文献：
  名称：

  Reactions of arylazosulfones with the conjugate bases of (tert-butoxycarbonyl)methyl and tosylmethyl isocyanide. Synthesis of substituted 1-arylimidazoles

  摘要：

  The reactions of arylazosulfones 1 (ArN=NSO2Ar') with the potassium salts of (tert-butoxycarbonyl)methyl 2 and tosylmethyl isocyanide 3 in DMSO afford 4,5-bis(tert-butoxycarbonyl)-4 and 4-tosyl-1-arylimidazoles 5, respectively. Yields of imidazoles 4 and 5 vary from moderate to excellent depending on the nature both of Ar in 1 and of the nucleophile (2 or 3) employed. A comparison of the results obtained with those relevant to the reactions of the same nucleophiles with nitrosobenzene in analogous experimental conditions provides useful mechanistic indications on the transformation of 1 to 4 or 5. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01108-8

文献信息

• Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400
  作者：Junmin Chen、Yimin Zhang、Wenyan Hao、Rongli Zhang、Fei Yi

  DOI：10.1016/j.tet.2012.11.014

  日期：2013.1

  An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.

  通过铜催化芳基卤化物与肼水溶液在PEG-400中的交叉偶联，描述了一种有效且方便的芳基肼合成方法。该方案适用于缺电子和富电子的芳基碘化物和溴化物，甚至适用于空间受阻的底物，芳基肼的收率良好至极佳。