trans-4-phenyl-3-[2-[2-(4-methylphenyl)ethenyl]phenyl]sydnone | 1260104-37-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: trans-4-phenyl-3-[2-[2-(4-methylphenyl)ethenyl]phenyl]sydnone
• CAS: 1260104-37-7
• 化学式: C₂₃H₁₈N₂O₂
• 分子量: 354.408
• InChiKey: SHKLXOHRVIWKPG-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  52.97
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-4-phenyl-3-[2-[2-(4-methylphenyl)ethenyl]phenyl]sydnone 以 苯 为溶剂， 反应 0.33h， 以67%的产率得到4-(4-methylphenyl)-3-phenyl-1H-1,2-benzodiazepine
  参考文献：
  名称：

  Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; intramolecular cyclization to 1,2-benzodiazepines and/or quinolines

  摘要：

  Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzo-diazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.013
• 作为产物：
  描述：

  在 乙酸酐 、 sodium carbonate decahydrate 作用下， 反应 168.0h， 以64 mg的产率得到trans-4-phenyl-3-[2-[2-(4-methylphenyl)ethenyl]phenyl]sydnone
  参考文献：
  名称：

  Synthesis and photochemistry of 3-(o-stilbeneyl)-4-H/Me/Ph-sydnones; intramolecular cyclization to 1,2-benzodiazepines and/or quinolines

  摘要：

  Stilbeneylsydnone derivatives were synthesized by a sequence of reactions in good yields. Irradiation of 3-stilbeneyl-4-methylsydnone 4 gives 1H-1,2-benzodiazepine derivative 7 as the main product along with 2-methylquinoline derivative 20. Irradiation of 3-stilbeneyl-4-phenylsydnone 5 afforded only 1H-1,2-benzodiazepine derivative 8 whereas on irradiation of 4-unsubstituted 3-stilbeneylsydnone 3 no benzodiazepine derivative was detected. An efficient novel photochemical approach to 1H-1,2-benzo-diazepines has been found from the new 3-(o-stilbeneyl)-4-substituted-sydnones via intramolecular 1,7-electrocyclization reaction of the photogenerated nitrile imines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.013

文献信息

• Synthesis of 3-(o-stilbenyl)sydnone and 3-(o-stilbenyl)-4-substituted-sydnone derivatives and their antitumor evaluation
  作者：Kristina Butković、Željko Marinić、Marija Šindler-Kulyk

  DOI：10.3998/ark.5550190.0012.a01

  日期：——

  stilbene-sydnone derivatives were synthesized by the following sequence of reactions: starting from methyl anthranilate via glycineand nitrosoglycine derivatives the corresponding 3-(o-carbomethoxyphenyl)-4-H/Me/Ph-sydnones were prepared and transformed to 3-(o-formylphenyl)-4-H/Me/Ph-sydnones, starting materials for Wittig reaction with various phosphonium salts to stilbenylsydnone derivatives. Final products

  通过以下反应顺序合成了一系列新的芪 - sydnone 衍生物：从邻氨基苯甲酸甲酯开始，通过甘氨酸和亚硝基甘氨酸衍生物，制备相应的 3-（邻碳甲氧基苯基）-4-H/Me/Ph-sydnones 并转化为 3 -(o-formylphenyl)-4-H/Me/Ph-sydnones，Wittig 与各种鏻盐反应生成芪基悉尼酮衍生物的原料。评估了最终产品对五种癌细胞系的细胞毒性特性，其中 cis-4-methyl-3-[2-[2-(4methylphenyl)ethenyl]phenyl] sydnone 5 和 cis-4-phenyl-3-[2 -[2-(4-氯苯基)乙烯基]苯基]sydnone 10 表现出最显着的活性。
• Spectral properties and photoreactivity of sydnonyl-stilbenes
  作者：U. Mazzucato、D. Pannacci、M. Šindler-Kulyk、K. Butković、A. Spalletti

  DOI：10.1016/j.jphotochem.2017.10.014

  日期：2018.1

  conditions. Flash photolysis measurements with nanosecond resolution were also carried out to obtain information on the transient intermediates responsible for the photoproducts found in the previous work. The oxygen effect on the photoproducts and the energy transfer from triplet donors were also investigated. The experimental results, supported by quantum chemical calculations, showed that different

  这项工作是在较早的工作之前进行的，在该工作中合成了一些对它们的生物学和生物医学应用感兴趣的亚砜酮衍生物，并在高强度和高底物浓度的辐照条件下研究了取代基对其光反应性的影响。本工作的目的是研究带有二苯乙烯部分的这些化合物中三种化合物的激发态的失活途径，并确定在软照射条件下竞争性荧光/光反应的量子产率。还进行了纳秒级分辨率的快速光解测量，以获取有关负责先前工作中发现的光产物的瞬态中间体的信息。还研究了氧对光产物的影响以及三重态供体的能量转移。由量子化学计算支持的实验结果表明，在亚砜环上不同的取代基可以驱动对不同产物的光反应性，从而证实了先前的工作结果。特别地，苯基取代有利于苯并二氮杂卓衍生物的形成。