(2Z)-2-[(4-chlorophenyl)methylidene]-3-phenyl-3,4-dihydropyrazol-2-ium-5-olate | 1426936-18-6

• 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: (2Z)-2-[(4-chlorophenyl)methylidene]-3-phenyl-3,4-dihydropyrazol-2-ium-5-olate
• CAS: 1426936-18-6
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: GRKSGURPQIAKKA-ODLFYWEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z)-2-[(4-chlorophenyl)methylidene]-3-phenyl-3,4-dihydropyrazol-2-ium-5-olate 、 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83%的产率得到methyl (3R,5R)-7-(tert-butyldimethylsilyloxy)-5-(4-chlorophenyl)-1-oxo-3-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

• Catalytic [3 + 3]-Cycloaddition for Regioselective Preparation of Tricyclic Oxadiazines
  作者：T. Prabhakar Reddy、A. Vamshi Krishna、Dhevalapally B. Ramachary

  DOI：10.1021/acs.orglett.8b02719

  日期：2018.11.16

  Agrochemically useful and structurally important, functionally rich tricyclic-oxadiazines were synthesized in very good yields with excellent diastereoselectivities through a catalytic [3 + 3]-cycloaddition from the readily available p-quinols, azomethine imines, and a catalytic amount of Brønsted base (KOtBu).

  通过从容易获得的对苯二酚，偶氮甲亚胺和催化量的Brønsted碱（KO t Bu）。
• 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。
• Diastereo‐ and Enantioselective Silver‐Catalyzed [3+3] Cycloaddition and Kinetic Resolution of Azomethine Imines with Activated Isocyanides
  作者：Ling‐Fei Tao、Sen Zhang、Fen Huang、Wen‐Tao Wang、Zhang‐Hong Luo、Linghui Qian、Jia‐Yu Liao

  DOI：10.1002/anie.202202679

  日期：2022.6.7

  diastereo- and enantioselective [3+3] cycloaddition of activated isocyanides with azomethine imines is reported for the first time. Under silver catalysis, a series of bicyclic 1,2,4-triazines were obtained in high yields with high stereoselectivities. The versatility of this system was further demonstrated by the late-stage functionalization of complex bioactive molecules and the kinetic resolution of racemic

  首次报道了活化异氰化物与偶氮甲碱亚胺的前所未有的非对映和对映选择性 [3+3] 环加成反应。在银催化下，以高收率和高立体选择性获得了一系列双环1,2,4-三嗪。复杂生物活性分子的后期功能化和外消旋甲亚胺的动力学拆分进一步证明了该系统的多功能性。
• Bicyclic Pyrazolidinone Derivatives from Diastereoselective Catalytic [3 + 3]-Cycloaddition Reactions of Enoldiazoacetates with Azomethine Imines
  作者：Yu Qian、Peter J. Zavalij、Wenhao Hu、Michael P. Doyle

  DOI：10.1021/ol400339c

  日期：2013.4.5

  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.