α-(Z)-3,4-(methylenedioxy)phenyl-N-phenylnitrone | 200341-04-4

• 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: α-(Z)-3,4-(methylenedioxy)phenyl-N-phenylnitrone
• 英文别名: (Z)-1-(benzo[d][1,3]dioxol-5-yl)-N-phenylmethanimine oxide；1-(1,3-benzodioxol-5-yl)-N-phenylmethanimine oxide
• CAS: 200341-04-4
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: ZYMPIMWKBKPKIX-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(Z)-3,4-(methylenedioxy)phenyl-N-phenylnitrone 、 二苯甲酰基乙炔 以23%的产率得到
  参考文献：
  名称：

  EL-DIN, AHMED, MOUKHTAR, NOUR;MOURAD, ABOUL-FETOUH, EL-SAID;MEKAMER, RAMA+, HETEROCYCLES, GPNTB CCCP, 1985, 23, N 5, 1155-1160

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒醛 、 亚硝基苯 在 L-脯氨酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以45%的产率得到α-(Z)-3,4-(methylenedioxy)phenyl-N-phenylnitrone
  参考文献：
  名称：

  脯氨酸介导的亚硝基苯合成硝酮的无金属方法

  摘要：

  已经建立了一种高效，无金属的方法，用于由脯氨酸介导的亚硝基苯和苯甲醛合成硝酮。该反应在室温下以甲醇为溶剂非常有效地进行。假定该反应涉及到先形成亚甲亚胺叶立德和亚硝基苯的[2 + 3]环加成，然后进行随后的[2 + 3]环加成可以提供所需的腈。

  DOI：

  10.1016/j.tet.2018.06.001

文献信息

• Synthesis of C, N-diaryl Nitrones from the Reduction of Nitroarene with Aromatic Aldehydes Promoted by Metallic Samarium
  作者：Xueshun Jia、Dafeng Li、Qing Huang、Li Zhu、Jian Li

  DOI：10.3184/030823407x218057

  日期：2007.5

  A mild and facile reduction of nitroarene with aromatic aldehydes promoted by metallic samarium to C, N-diaryl nitrones in moderate yields has been developed.

  在金属钐的促进下，开发出了一种温和而简便的方法，将硝基炔与芳香醛还原为 C，N-二芳基硝基腈，收率适中。
• 1,3-Dipolar Cycloaddition Reactionsof Nitrones to Prop-1-ene-1,3-sultone
  作者：Lun-Zu Liu、Li Tian、Guo-Yan Xu、Yong Ye

  DOI：10.1055/s-2003-40201

  日期：——

  The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.

  丙-1-烯-1,3-磺内酯（1）与多种亚硝基化合物（2）的反应良好地生成了新颖的[3+2]环加成产物3、4和5。与苯基亚硝基化合物的环加成反应中获得了优异的区位选择性和立体选择性。
• α-Aryl-N-aryl nitrones: Synthesis and screening of a new scaffold for cellular protection against an oxidative toxic stimulus
  作者：A.C. Matias、G. Biazolla、G. Cerchiaro、A.F. Keppler

  DOI：10.1016/j.bmc.2015.12.007

  日期：2016.1

  Nitrone-containing compounds are commonly employed as spin traps of free radical species in chemical and biological studies. Some molecules as alpha-phenyl-N-t-butyl nitrone (PBN) and its derivatives have been tested as potential drugs to treat oxidative stress related diseases, as Alzheimer and stroke for example. In this work we report the design and the synthesis of alpha-aryl-N-aryl nitrones and their cytoprotection profile on human neuroblastoma cells (SH-SY5Y) under induced oxidative stress. All the nine synthesized nitrones showed a significant response at low micromolar concentration. The selected compound 8 (alpha-phenyl-N-phenyl nitrone) increased the reduced glutathione (GSH) levels by 65% and lowered the necrotic cell death from 25.8% to 3.8%. Based on our data, the designed highly conjugated nitrone double-bond skeleton can be considered as a good scaffold for further studies regarding oxidative stress-related diseases. (c) 2015 Elsevier Ltd. All rights reserved.
• Indium mediated allylation of CN compounds in aqueous media
  作者：H.M Sampath Kumar、S Anjaneyulu、E Jagan Reddy、J.S Yadav

  DOI：10.1016/s0040-4039(00)01676-2

  日期：2000.11
• Synthesis of New 2-Chloro-4-(3-Aryl-2,4-Diphenyl-3H-Triazolidine-5-on-1-yl)Quinoline-3-Carbonitriles by a Cyclo-Addition Route Using Carbodiimides and Nitrones. A Novel Thermal Decomposition to 4-Aminoquinolines
  作者：Ramadan AhmedMekheimer

  DOI：10.1080/00397919808004913

  日期：1998.10