diisopropyl 1-(4-methylphenyl)-hydrazine-1,2-dicarboxylate

• 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: diisopropyl 1-(4-methylphenyl)-hydrazine-1,2-dicarboxylate
• 英文别名: diisopropyl 1-(4-methylphenyl)hydrazine-1,2-dicarboxylate；1,2-bis(isopropoxycarbonyl)-1-(4-methylphenyl)hydrazine；propan-2-yl N-(4-methylphenyl)-N-(propan-2-yloxycarbonylamino)carbamate
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: QGWPYHZTAGJBIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  偶氮二甲酸二异丙酯 、 对苄基三氟甲磺酸 在 sodium hydride 、 copper(I) oxide 、 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 以79%的产率得到diisopropyl 1-(4-methylphenyl)-hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  氢化钠诱导偶氮二甲磺酸二异丙酯的 N-芳基化三氟甲磺酸芳基酯

  摘要：

  报道了一种在无配体氧化铜 (I) 催化剂存在下，在 80°C 下，在 N，N-二甲基甲酰胺中，通过芳基三氟甲磺酸盐对偶氮二羧酸二异丙酯和氢化钠衍生的阴离子物质进行分子间 N-芳基化的方法。多种官能化的三氟甲磺酸芳基酯通过该方法有效偶联。

  DOI：

  10.1055/s-0034-1380143

文献信息

• Copper(I) Iodide Catalyzed Formation of Aryl Hydrazides from a Mitsunobo Reagent and Aryl Halides
  作者：Issa Yavari、Majid Ghazanfarpour-Darjani、Yazdan Solgi、Salome Ahmadian

  DOI：10.1055/s-0030-1260802

  日期：2011.7

  The Mitsonubo reagent (triphenylphosphine and dialkyl azodicarboxylates) was employed as a potential anionic nucleophile in a reaction involving aryl halides to produce aryl hydrazides. Aryl iodides and bromides, with electron-withdrawing as well as electron-releasing groups on the aromatic ring, undergo coupling reactions in good yields. The optimized conditions are developed for aryl iodides at room

  Mitsonubo 试剂（三苯基膦和偶氮二羧酸二烷基酯）在涉及芳基卤化物以产生芳基酰肼的反应中用作潜在的阴离子亲核试剂。芳基碘化物和溴化物在芳环上具有吸电子和放电子基团，以良好的产率进行偶联反应。开发了室温下芳基碘和 60-75 °C 芳基溴的优化条件。
• Cross-coupling reaction of aryl diazonium salts with azodicarboxylate using FeCl₂
  作者：M. Khalaj、M. Ghazanfarpour-Darjani

  DOI：10.1039/c5ra15875c

  日期：——

  Arene diazonium salts have been employed as the aryl source in reaction with dialkyl azodicarboxylates to form N-aryl hydrazide derivatives. The optimum conditions are developed using FeCl2 in DMSO at 25 °C for 2 h. Various functional groups were tolerated under the optimum conditions.

  在与偶氮二羧酸二烷基酯反应形成N-芳基酰肼衍生物时，已将芳族重氮盐用作芳基源。在25°C下在DMSO中使用FeCl 2 2 h来开发最佳条件。在最佳条件下可以耐受各种官能团。
• Copper-catalyzed C–N bond formation using dialkyl azodicarboxylate as the amination reagent
  作者：Alireza Samzadeh-Kermani

  DOI：10.1016/j.tetlet.2015.12.036

  日期：2016.1

  An efficient copper-catalyzed reaction for C-N bond formation using aryl halides, dialkyl azodicarboxylate, and a hydride source is reported. Using this procedure, aryl iodides reacted at ambient conditions, while aryl bromides required heating to 60 degrees C to accomplish the transformation. Various functional groups were tolerated under the optimum conditions. (C) 2015 Elsevier Ltd. All rights reserved.
• Phenanthroline Ligands in Aryl Palladium Hydrazinato Complexes: Catalysts for Efficient Coupling of Azo Componds with Aryl Boronic Acids
  作者：Kilian Muñiz、Alvaro Iglesias

  DOI：10.1002/anie.200700288

  日期：2007.8.20
• Sodium Hydride Induced N-Arylation of Diisopropyl Azodicarboxylate by Aryl Trifluoromethanesulfonates
  作者：Issa Yavari、Majid Ghazanfarpour-Darjani、Mohammad Bayat、Alaleh Malekafzali

  DOI：10.1055/s-0034-1380143

  日期：——

  method for intermolecular N-arylation of the anionic species derived from diisopropyl azodicarboxylate and sodium hydride by aryl trifluoromethanesulfonates, in the presence of a ligand-free copper(I) oxide catalyst at 80 °C in N , N -dimethylformamide, is reported. A variety of functionalized aryl triflouromethanesulfonates were efficiently coupled by this method.

  报道了一种在无配体氧化铜 (I) 催化剂存在下，在 80°C 下，在 N，N-二甲基甲酰胺中，通过芳基三氟甲磺酸盐对偶氮二羧酸二异丙酯和氢化钠衍生的阴离子物质进行分子间 N-芳基化的方法。多种官能化的三氟甲磺酸芳基酯通过该方法有效偶联。