(Z)-2-benzylidene-3-(4-bromophenyl)-5-oxopyrazolidin-2-ium-1-ide | 1426936-22-2

• 英文名称: (Z)-2-benzylidene-3-(4-bromophenyl)-5-oxopyrazolidin-2-ium-1-ide
• CAS: 1426936-22-2
• 化学式: C₁₆H₁₃BrN₂O
• 分子量: 329.196
• InChiKey: MVKGREFUCBFCKI-ODLFYWEKSA-N

计算性质

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

• 作为反应物：
  描述：

  (Z)-2-benzylidene-3-(4-bromophenyl)-5-oxopyrazolidin-2-ium-1-ide 、 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82%的产率得到methyl (3R,5R)-3-(4-bromophenyl)-7-((tert-butyldimethylsilyl)oxy)-1-oxo-5-phenyl-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

• Synthesis of pyrazolotetrazepin-7-ones from 1,3,5-triazinanes with N,N′-cyclic azomethine imines via a formal (5 + 2) pathway
  作者：Bin Cheng、Yixuan He、Hongjian Yang、Hui Li、Xinping Zhang、Wei Xu、Haiyan Sun、Taimin Wang、Hongbin Zhai

  DOI：10.1016/j.tet.2021.132130

  日期：2021.6

  The synthesis of pyrazolotetrazepin-7-ones from 1,3,5-triazinanes with N,N′-cyclic azomethine imines was achieved via a formal (5 + 2) pathway under thermal conditions. The annulation reaction is catalyst-free and additive-free.

  由 1,3,5-三嗪烷与 N,N'-环状偶氮甲亚胺合成 pyrazolotetrazepin-7-ones 是通过正式的 (5 + 2) 途径在热条件下实现的。环化反应是无催化剂和无添加剂的。
• 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。