2,3',4-Trinitro-(E)-stilben | 61599-65-3

• 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: 2,3',4-Trinitro-(E)-stilben
• 英文别名: 2,4-dinitro-1-[(E)-2-(3-nitrophenyl)ethenyl]benzene
• CAS: 61599-65-3
• 化学式: C₁₄H₉N₃O₆
• 分子量: 315.242
• InChiKey: OUXDWRIVHNBVLH-SNAWJCMRSA-N

物化性质

• 沸点：
  471.8±45.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3',4-Trinitro-(E)-stilben 以 2-甲基四氢呋喃 为溶剂， 生成 2,4-Dinitro-1-[(Z)-2-(3-nitro-phenyl)-vinyl]-benzene
  参考文献：
  名称：

  Photophysics and photochemistry of trans-4-nitrostilbenes and trans-2,4-dinitrostilbenes: Effect of intramolecular charge transfer

  摘要：

  AbstractThe photophysical and photochemical properties of trans‐R‐2′,4′‐dinitrostilbene (II) and a series of trans‐R‐2′,4′‐dinitrostilbenes (II‐R, R: 2‐NO2, 3‐NO2, 4‐Br, 4‐F, 4‐Me, 4‐C3H7, 4‐OCH2C6H5, 3,4,5‐(OMe)3, 4‐OEt, 4‐NMe2, 4‐NEt2) were studied in solution as a function of solvent polarity and temperature. The quantum yield of fluorescence (Φf) is very small for all II‐R at 25°C. At −196°C Φf is moderate for several derivatives in 2‐methyltetrahydrofuran (MTHF) but strongly enhanced for those bearing electron donating substituents. For the latter compounds the quantum yield of trans → cis photoisomerization is low, but for the other compounds Φt → c is substantial (0.2‐0.5 in toluene or MTHF at room temperature). The triplet state absorbs typically in a broad spectral range; its lifetime (τT) lies in the 20‐200 ns range and is longer for R = 4‐NEt2; at −196°C τT of all II‐R approaches milliseconds. The results are compared with those of trans‐4‐R‐4′‐nitrostilbenes (I‐R, R: NO2, H, OMe, NH2, NMe2, NEt2). Phosphorescence of singlet molecular oxygen was observed for several mono‐ and dinitrostilbenes at room temperature. Generally, the quantum yield of singlet oxygen formation is much smaller than that of intersystem crossing into the triplet state. The triplet mechanism accounts for trans→cis photoisomerization and the contribution of this pathway is lowered by intramolecular electron transfer to the nitro group(s). The similarities and differences between I‐R and II‐R type compounds and the effects of intramolecular charge transfer are discussed.

  DOI：

  10.1002/bbpc.19981020505
• 作为产物：
  描述：

  2,4-二硝基甲苯 、 间硝基苯甲醛 在 四氢吡咯 作用下， 反应 0.01h， 以80%的产率得到2,3',4-Trinitro-(E)-stilben
  参考文献：
  名称：

  MICROWAVE-INDUCED SYNTHESIS OF NITROSTILBENES UNDER NEAT CONDITION

  摘要：

  Nitrostilbenes 3a-e were synthesized in good yield using microwave under neat conditions, whereas heating at 90 degreesC resulted in poorer yields of products.

  DOI：

  10.1081/scc-100103315

文献信息

• Highly double selective nitration of nitrostilbenes over zeolite
  作者：Jun-Hui Xu、Jian-Ping Wei、Zheng Hao、Qing-Guo Ma、Xin-Hua Peng

  DOI：10.1039/c4cc04688a

  日期：——

  A feasible zeolite-assisted ortho C–H nitration of nitrostilbenes has been developed for the first time.

  首次开发了一种可行的沸石辅助的亚甲基C-H硝化反应，用于亚硝基芳基丙烯酸酯的合成。
• Synthesis of (<i>E</i>) α,2,4-Trinitrostilbenes from (<i>E</i>) 2,4-Dinitrostilbenes
  作者：S. Saravanan、P. C. Srinivasan

  DOI：10.1081/scc-120018685

  日期：2003.1.5

  A convenient synthesis of (E) alpha,2,4-trinitrostilbenes 2a-d from (E) 2,4-dinitrostilbenes 1a-e by direct nitration is reported. Isomerization of the trans geometry of the reactant stilbenes to cis in the products was found. The structures of stilbenes 2a, 2c and 2d were confirmed by XRD.