3-(3,4-methylenedioxyphenyl)sydnone | 4266-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(3,4-methylenedioxyphenyl)sydnone
• 英文别名: 3-<3,4-Methylendioxy-phenyl>-sydnon；N-(3,4-methylenedioxyphenyl)sydnone；3-benzo[1,3]dioxol-5-yl-sydnone；3-(2H-1,3-Benzodioxol-5-yl)-1,2,3-oxadiazol-3-ium-5-olate；3-(1,3-benzodioxol-5-yl)oxadiazol-3-ium-5-olate
• CAS: 4266-86-8
• 化学式: C₉H₆N₂O₄
• 分子量: 206.158
• InChiKey: ABZNKOMGLTZYJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-methylenedioxyphenyl)sydnone 在 palladium diacetate 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (E,Z)-1-(benzo[d][1,3]dioxol-5-yl)-5-(phenylcarbamoyl)-3-(4-(trifluoromethyl)phenyl)formazan
  参考文献：
  名称：

  4-Phenyl-1,2,4-trizoline-3,5-二酮的水参与开环，用于“光点击”原位访问氨基甲酰甲臜光电开关

  摘要：

  4-苯基-1,2,4-三唑啉-3,5-二酮(PTAD) 在水性介质中易腐烂的性质始终被认为是一种副作用。PTAD 的快速褪色启发了我们探索其水解机制。在此，发现光生腈亚胺是一种超快速捕获剂，可与具有 umpolung 效应的开环水解产物“点击”，从而产生前所未有的氨基甲酰基甲臜作为光可切换键。

  DOI：

  10.1002/asia.202101239
• 作为产物：
  描述：

  在 乙酸酐 作用下， 反应 5.0h， 生成 3-(3,4-methylenedioxyphenyl)sydnone
  参考文献：
  名称：

  Synthesis of 2H-Indazoles by the [3 + 2] Dipolar Cycloaddition of Sydnones with Arynes

  摘要：

  A rapid and efficient synthesis of 2H-indazoles has been developed using a [3 + 2] dipolar cycloaddition of sydnones and arynes. A series of 2H-indazoles have been prepared in good to excellent yields this protocol, and subsequent Pd-catalyzed coupling reactions can be applied to the halogenated products to generate a structurally diverse library of indazoles.

  DOI：

  10.1021/jo201605v

文献信息

• Photo-accelerated “click” reaction between diarylsydnones and ring-strained alkynes for bioorthogonal ligation
  作者：Xiaocui Zhang、Xueting Wu、Shichao Jiang、Jingshuo Gao、Zhuojun Yao、Jiajie Deng、Linmeng Zhang、Zhipeng Yu

  DOI：10.1039/c9cc02882j

  日期：——

  A novel photo-click ligation reaction between diarylsydnones and ring-strained alkynes, exhibiting decent bioorthogonality, was established under 405 nm light irradiation.

  一种新颖的光点击连接反应在405纳米光照射下，建立了二芳基苯酮和环张力炔之间的反应，表现出良好的生物正交性。
• Synthesis of 2<i>H</i>-Indazoles by the [3 + 2] Cycloaddition of Arynes and Sydnones
  作者：Chunrui Wu、Yuesi Fang、Richard C. Larock、Feng Shi

  DOI：10.1021/ol100586r

  日期：2010.5.21

  A rapid and efficient synthesis of 2H-indazoles has been developed, which involves the [3 + 2] dipolar cycloaddition of arynes and sydnones. The process proceeds under mild reaction conditions in good to excellent yields.
• Pd-catalyzed oxidative coupling of monosubstituted sydnones and terminal alkynes
  作者：Chunrui Wu、Pan Li、Yuesi Fang、Jingjing Zhao、Weichao Xue、Yang Li、Richard C. Larock、Feng Shi

  DOI：10.1016/j.tetlet.2011.05.058

  日期：2011.7

  The Pd-catalyzed oxidative coupling of N-substituted sydnones and terminal alkynes offers a quick, one-step synthesis of 4-alkynylsydnones in moderate to good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• [1,3]-Dipolar cycloaddition of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)-1H-indole
  作者：Yaşar Dürüst、Akın Sağırlı、Benson M. Kariuki、David W. Knight

  DOI：10.1016/j.tet.2014.04.083

  日期：2014.9

  [1,3]-Dipolar cycloadditions of N-aryl sydnones to benzothiophene 1,1-dioxide, 1-cyclopropylprop-2-yn-1-ol and 1-(prop-2-ynyl)indole gave fused pyrazole derivatives when carried out in refluxing toluene. While the first two dipolarophiles gave single regioisomers, this indolic derivative gave mixtures, the ratios of which appeared to be controlled by the phenyl substituents. Their structures were identified in the usual manner, supported by single crystal X-ray diffraction measurements. (C) 2014 Elsevier Ltd. All rights reserved.
• Microwave-Assisted Coupling Reaction of <i>N</i>-Aryl Sydnones with 2-Nitromethylenethiazolidine: Unexpected Formation of (<i>Z</i>)-2-(Nitro((<i>E</i>)-<i>p</i>-substitutedphenyldiazenyl)methylene)thiazolidines
  作者：Yaşar Dürüst、Akın Sağırlı

  DOI：10.1021/jo5010229

  日期：2014.7.3

  Reaction of N-aryl sydnones with 2-nitro-methylenethiazolidine straightforwardly gives rise to the formation of (Z)-2-(nitro((E)-p-substitutedphenyldiazeny1)methylene)thiazolidines in xylene and dimethoxyethane under microwave irradiation. A meaningful and plausible mechanism for this transformation is proposed, which anticipates the extrusion of an aceto-lactone-like moiety before a coupling occurs. The structures of all the new compounds were identified on the basis of the data obtained from the NMR, IR. X-ray diffraction spectra, HRMS measurements, and physical characteristics.