trans-4′-chloro-2,4,6-trinitrostilbene | 61599-70-0

• 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′-chloro-2,4,6-trinitrostilbene
• 英文别名: 4'-chloro-2,4,6-trinitro-trans-stilbene；4'-Chlor-2,4,6-trinitro-trans-stilben；2,4,6-Trinitro-4'-chlor-(E)-stilben；2-[(E)-2-(4-chlorophenyl)ethenyl]-1,3,5-trinitrobenzene
• CAS: 61599-70-0
• 化学式: C₁₄H₈ClN₃O₆
• 分子量: 349.687
• InChiKey: SSHFAPSAKDWQOY-ZZXKWVIFSA-N

物化性质

• 沸点：
  474.7±45.0 °C(Predicted)
• 密度：
  1.588±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 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：

  trans-4′-chloro-2,4,6-trinitrostilbene 在 potassium carbonate 、 苄硫醇 、 磺酰氯 作用下， 以 N-甲基吡咯烷酮 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 2-(4-chlorophenyl)-4,6-dinitrobenzo[b]thiophene
  参考文献：
  名称：

  Synthesis of 2-aryl-4,6-dinitrobenzo[b]thiophenes from 2,4,6-trinitrotoluene

  摘要：

  A method for the synthesis of previously unknown 2-aryl-4,6-dinitrobenzo[b]thiophenes and their 3-chloro derivatives has been developed based on the replacement of ortho-NO2 in (E)-2,4,6-trinitrostilbenes on treatment with PhCH2SH/K2CO3 followed by transformations of the resulting 2-benzylthio-4,6-dinitrostilbenes by treatment with SO2Cl2.

  DOI：

  10.1070/mc2004v014n01abeh001859
• 作为产物：
  描述：

  2,4,6-三硝基甲苯 、 4-氯苯甲醛 在 HTc-4-Cal 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以70%的产率得到trans-4′-chloro-2,4,6-trinitrostilbene
  参考文献：
  名称：

  Synthesis of Polynitrostilbenes using Activated Hydrotalcites as Heterogeneous Base Catalysts

  摘要：

  本研究介绍了一种高效、直接的方法，即在活化的氢铝酸盐作为异相催化剂的催化下，通过多硝基苯烯与芳香醛的缩合，合成具有 ( E) 构型的多硝基苯烯。

  DOI：

  10.3184/174751914x14109571360770

文献信息

• Synthesis of Polynitrostilbenes using Activated Hydrotalcites as Heterogeneous Base Catalysts
  作者：Junhui Xu、Jianping Wei、Qingguo Ma、Xinhua Peng

  DOI：10.3184/174751914x14109571360770

  日期：2014.10

  An efficient and straight for ward synthesis of polynitrostilbenes with the ( E)-configuration by the condensation of polynitroarenes with aromatic aldehydes, catalysed by activated hydrotalcites as heterogeneous catalysts is described.

  本研究介绍了一种高效、直接的方法，即在活化的氢铝酸盐作为异相催化剂的催化下，通过多硝基苯烯与芳香醛的缩合，合成具有 ( E) 构型的多硝基苯烯。
• Nucleophilic replacement of the nitro group in E-2,4,6-trinitrostilbenes by O- and S-nucleophiles. Synthesis of 2-aryl-4-X-6-nitrobenzo[b]thiophenes
  作者：O. Yu. Sapozhnikov、V. V. Mezhnev、M. D. Dutov、V. V. Kachala、N. A. Popov、S. A. Shevelev

  DOI：10.1007/s11172-005-0309-1

  日期：2005.3

  nucleophilic substitution for the nitro group in E-2,4,6-trinitrostilbenes under the action of arene- and alkanethiols or phenols in the presence of inorganic bases was studied. Products of o-NO2 group replacement in the presence of PhCH2SH were used to obtain earlier unknown 2-aryl-4,6-dinitrobenzo[b]thiophenes and their 3-chloro derivatives. In these fused heterocycles, the 4-NO2 group can be selectively displaced

  研究了在无机碱存在下在芳烃和烷硫醇或酚的作用下，E-2,4,6-三硝基二苯乙烯中硝基的亲核取代方向。在 PhCH2SH 存在下，o-NO2 基团置换的产物用于获得早期未知的 2-芳基-4,6-二硝基苯并 [b] 噻吩及其 3-氯衍生物。在这些稠合杂环中，4-NO2 基团可以被亲核试剂选择性取代。
• Highly competitive and selective electrophilic catalytic bromination of polynitro stilbenes with molecular bromine in the presence of ZnO/H-beta-25
  作者：Zheng Hao、Junhui Xu、Jiangfeng Huang、Xinhua Peng

  DOI：10.1016/j.catcom.2016.12.005

  日期：2017.3

  efficient methodology for bromination of polynitro stilbenes using molecular bromine as brominating agent over ZnO/H-beta-25 has been developed, which is conducted under mild condition, in good to high yield with excellent regio- and chemo-selectivities. Preliminary mechanistic studies have shown that this reaction most likely occurs via a noncovalent binding of molecular bromine to benzene ring involving

  已经开发出一种在分子条件下作为溴化剂在ZnO /H-β-25上溴化多硝基苯乙烯的有效方法，该方法在温和的条件下以高至高收率，优异的区域选择性和化学选择性进行。初步的机理研究表明，该反应最有可能是通过分子溴与苯乙烯基结构的苯环的非共价结合而发生的。
• Pfeiffer, Chemische Berichte, 1915, vol. 48, p. 1796
  作者：Pfeiffer

  DOI：——

  日期：——
• Synthesis of Polynitrostilbenes from 2,4,6-Trinitro-<i>M</i>-Xylene and 2,4,6-Trinitrotoluene by a Microwave-Assisted Solvent Free Method
  作者：Junhui Xu、Fangmei Li、Jianping Wei、Xinhua Peng

  DOI：10.3184/174751914x13944453321075

  日期：2014.4

  A microwave-assisted method for the synthesis of polynitrostilbenes involving the condensation of 2,4,6-trinitro-m-xylene and 2,4,6-trinitrotoluene with aryl aldehydes in the presence of piperidine and silica-gel is reported. Compared with conventional methods, a shorter reaction time is required and this method has a lower environmental impact. A mechanism for the reaction is also proposed and supported

  报道了一种微波辅助合成聚硝基二甲苯的方法，包括在哌啶和硅胶存在下将 2,4,6-三硝基间二甲苯和 2,4,6-三硝基甲苯与芳基醛缩合。与传统方法相比，该方法所需的反应时间更短，对环境的影响更小。紫外-可见吸收光谱也提出并支持了该反应的机制。