diisopropyl 1-propionylhydrazine-1,2-dicarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diisopropyl 1-propionylhydrazine-1,2-dicarboxylate
• 英文别名: propan-2-yl N-propanoyl-N-(propan-2-yloxycarbonylamino)carbamate
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: OUIFKFCPBWKNLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diisopropyl 1-propionylhydrazine-1,2-dicarboxylate 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 N-羟基丙酰胺
  参考文献：
  名称：

  醛由光有机催化一锅合成异羟肟酸

  摘要：

  描述了一种有效的一锅法从醛和羟胺合成异羟肟酸的方法。快速，可见光介导的偶氮二羧酸二烷基酯的无金属加氢酰化反应用于随后添加盐酸羟胺的过程。在该反应中使用了一系列脂族和芳族醛，以高产率或优异产率得到异羟肟酸。在抗癌药伏立诺他的合成中证明了当前方法的应用。

  DOI：

  10.1002/chem.201600333
• 作为产物：
  描述：

  丙醛 、 diisopropyl (E)-azodicarboxylate 在 dirhodium tetraacetate 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以97%的产率得到diisopropyl 1-propionylhydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  偶氮二羧酸盐对过渡金属催化醛的CH活化

  摘要：

  在温和的条件下，乙酸铑催化醛与N N键的活化形式之间的加氢酰化反应，从而可以有效地获得各种肼基酰亚胺。在末端和内部位置均具有不饱和醛的情况下，相对于烯型反应，醛类CH活化具有良好的选择性。

  DOI：

  10.1021/jo035456o

文献信息

• Zinc Acetate as a Catalyst for the Hydroacylation Reaction of Azodicarboxylates with Aldehydes
  作者：Yuancheng Qin、Dan Zhou、Mingjun Li

  DOI：10.2174/157017812800233741

  日期：2012.4.24

  Zn(OAc)2·2H2O is found to be an effective catalyst for the hydroacylation reaction of azodicarboxylates with aldehydes. A wide range of aldehydes, including aliphatic, aromatic and heterocyclic compounds, was considered. Most of the hydroacylation reactions afforded the hydroacylation products in good to excellent yields. The overall system is simple, economical and has practical advantages for construction of carbon-nitrogen bonds.

  研究发现，Zn(OAc)2-2H2O 是偶氮二甲酸盐与醛类发生加氢酰化反应的有效催化剂。研究对象包括脂肪族、芳香族和杂环化合物等多种醛类。大多数加氢酰化反应都能得到加氢酰化产物，收率从良好到极佳。整个系统简单、经济，在构建碳氮键方面具有实际优势。
• Highly efficient copper-catalyzed hydroacylation reaction of aldehydes with azodicarboxylates
  作者：Yuancheng Qin、Qiang Peng、Jinsheng Song、Dan Zhou

  DOI：10.1016/j.tetlet.2011.08.165

  日期：2011.11

  The hydroacylation reaction of aldehydes with azodicarboxylates catalyzed by copper(II) acetate monohydrate has been reported. The reaction of various aldehydes gave the corresponding hydroacylation products in 60–98% yields under mild conditions. The method is simple, economical, and has practical advantages for the construction of the carbon–nitrogen bonds.

  已经报道了由乙酸铜（II）一水合物催化的醛与偶氮二羧酸酯的加氢酰化反应。在温和条件下，各种醛的反应以60-98％的产率提供了相应的加氢酰化产物。该方法简单，经济，在构建碳-氮键方面具有实际优势。
• CuO Nanoparticles Supported on Silica: A Simple, Efficient, and Recyclable Catalyst for Hydroacylation Reactions of Aldehydes with Azodicarboxylate
  作者：Suleman M. Inamdar、Vinod K. More、Sisir K. Mandal

  DOI：10.1246/cl.2012.1484

  日期：2012.11.5

  We describe a green and efficient procedure for the hydroacylation of aldehydes with diisopropyl azodicarboxylate, using CuO nanoparticles supported on silica (CuO-np/SiO2) as a catalyst, in good to excellent yields. A wide range of aldehydes, including aromatic and aliphatic compounds, were considered. The catalyst is found to be truly heterogeneous in the reaction mixture and can be reused without loss of catalytic activity.

  我们描述了一种绿色高效的程序，利用二异丙基偶氮二甲酸酯对醛进行水解酰化反应，采用以二氧化硅为载体的铜氧化物纳米粒子（CuO-np/SiO2）作为催化剂，反应产率良好至优秀。考虑了广泛的醛类，包括芳香族和脂肪族化合物。实验发现，催化剂在反应混合物中真正具有异相特性，并且可以重复使用而不丧失催化活性。
• A Practical and Highly Efficient Hydroacylation Reaction of Azodicarboxylates with Aldehydes in Water
  作者：Allan Headley、Bukuo Ni、Qianying Zhang、Erica Parker

  DOI：10.1055/s-0030-1258056

  日期：2010.10

  The very efficient hydroacylation reaction of azodicarboxylates, with various aldehydes, was carried successfully out at room temperature in water without the use of a catalyst to obtain a variety of hydrazine imide products in high yields. A wide range of aldehydes, including aliphatic and aromatic compounds, was considered, and the reaction is believed to proceed via a radical mechanism, in which

  偶氮二羧酸酯与各种醛的非常有效的加氢酰化反应在室温下在水中成功进行，无需使用催化剂，以高产率获得各种肼酰亚胺产物。考虑了多种醛，包括脂肪族和芳香族化合物，并且该反应被认为是通过自由基机制进行的，其中水在稳定自由基中间体方面起着不可或缺的作用。
• Ionic Liquid (IL) as an Effective Medium for the Highly Efficient Hydroacylation Reaction of Aldehydes with Azodicarboxylates
  作者：Bukuo Ni、Qianying Zhang、Satish Garre、Allan D. Headley

  DOI：10.1002/adsc.200800808

  日期：2009.4

  Abstractmagnified imageThe highly efficient hydroacylation reaction of aldehydes with azodicarboxylates has been carried out in the ionic liquid,1‐n‐butyl‐3‐methylimidazolium bis(trifluoromethanesulfonyl)imide, [BMIM] [NTf2]. The products were readily separated by extraction from the reaction medium and the ionic liquid could be recycled up to 8 times and the yields of the reactions were not affected. Compared to conventional solvents, high yields were achieved with aliphatic saturated aldehydes, and the reaction can be conducted under normal to mild conditions without the use of a catalyst.