| 1426936-19-7

• CAS: 1426936-19-7
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: SOITYKRJBXGETK-UNOMPAQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  、 methyl 3-tert-butyldimethylsilyloxy-2-diazobut-3-enoate 在 dirhodium tetraacetate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以80%的产率得到methyl (3R,5R)-7-(tert-butyldimethylsilyloxy)-1-oxo-3-phenyl-5-p-tolyl-2,3,5,8-tetrahydro-1H-pyrazolo[1,2-a]pyridazine-6-carboxylate
  参考文献：
  名称：

  Bicyclic Pyrazolidinone Derivatives from Diastereoselective Catalytic [3 + 3]-Cycloaddition Reactions of Enoldiazoacetates with Azomethine Imines

  摘要：

  A highly regio- and diastereoselective synthesis of bicyclic pyrazolidinone derivatives by rhodium(II) acetate catalyzed [3 + 3]-annulation with enoldiazoacetates and azomethine imines has been achieved in high yield. A vinylogous reaction of the metal enol carbene with the azomethine imine Initiates [3 + 3]-cycloaddition, whereas reaction at the carbene center effects N-N-cleavage of the azomethine imine.

  DOI：

  10.1021/ol400339c

文献信息

• Copper(II)-Catalyzed Asymmetric 1,3-Dipolar [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines with Azoalkenes
  作者：Liang Wei、Zuo-Fei Wang、Lu Yao、Guofu Qiu、Haiyan Tao、Hua Li、Chun-Jiang Wang

  DOI：10.1002/adsc.201600961

  日期：2016.12.22

  copper(II)‐catalyzed enantioselective 1,3‐dipolar [3+4] cycloaddition of azomethine imines with in situ formed azoalkenes has been realized. This strategy provides a facile access to biologically important 1,2,4,5‐tetrazepine derivatives in high yield with exclusive regioselectivity and high stereoselectivity. Moreover, enantioenriched azomethine imines could be obtained via an efficient kinetic resolution

  已经实现了前所未有的铜（II）催化的对偶氮亚胺亚胺与原位形成的偶氮烯烃的对映选择性1,3-偶极[3 + 4]环加成反应。这种策略可以轻松获得具有生物学上重要的1,2,4,5-四氮杂衍生物的高产率，且具有独特的区域选择性和高立体选择性。此外，可以使用相同方法通过有效的动力学拆分获得对映体富集的甲亚胺亚胺。
• Diastereoselective addition of redox active esters to azomethine imines by electrosynthesis
  作者：Ludovic Leleu、Thomas Martzel、Arona Fall、Morgane Sanselme、Vincent Levacher、Sylvain Oudeyer、Jean-François Brière

  DOI：10.1039/d2cc01795d

  日期：——

  N-(acyloxy)phthalimide esters led to an efficient and highly stereoselective addition (85 : 15 to 95 : 5 dr) of putative radical species to chiral (racemic and enantioenriched) C5-substituted azomethine imines to provide an array of 31 polyaminated hydrazine derivatives as a single diastereoisomer.

  由于在未分裂的电池中没有金属和催化剂的电化学条件，一系列易于获得的氧化还原活性N-（酰氧基）邻苯二甲酰亚胺酯导致了推定的高效和高度立体选择性加成（85 : 15 至 95 : 5 博士）自由基物种对手性（外消旋和对映体富集）C5-取代的偶氮甲亚胺提供一系列 31 种多胺化肼衍生物作为单一的非对映异构体。
• Iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light
  作者：Arona Fall、Mihaela Magdei、Mariia Savchuk、Sylvain Oudeyer、Hélène Beucher、Jean-François Brière

  DOI：10.1039/d4cc01766h

  日期：——

  Herein, we disclose an eco-efficient redox-neutral iron-catalyzed decarboxylative radical addition to chiral azomethine imines upon visible light (427 nm) giving cyclic hydrazine derivatives with dr ranging from 82 : 18 to >96 : 4. This earth-abundant metal promoted sequence proceeds efficiently under ligand-free conditions based on a LMCT process and opens a route to new chiral heterocycles.

  在此，我们公开了一种生态高效的氧化还原中性铁催化脱羧基自由基加成反应，在可见光（427 nm）下与手性偶氮甲碱亚胺发生加成，得到环状肼衍生物，dr范围为82:18至>96:4。这种地球丰富的金属基于LMCT过程，促进的序列在无配体条件下有效进行，并开辟了新的手性杂环的途径。