3,6-bis(4-chlorobenzyl)-1,2,4,5-tetrazine | 71200-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-bis(4-chlorobenzyl)-1,2,4,5-tetrazine
• 英文别名: 3,6-bis(4-chlorobenzyl)-s-tetrazine；3,6-bis-(4-chloro-benzyl)-[1,2,4,5]tetrazine；3,6-Bis[(4-chlorophenyl)methyl]-1,2,4,5-tetrazine
• CAS: 71200-54-9
• 化学式: C₁₆H₁₂Cl₂N₄
• 分子量: 331.204
• InChiKey: ZXZPXSMTZOSSID-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C(Solv: ethanol (64-17-5))
• 沸点：
  538.4±60.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-bis(4-chlorobenzyl)-1,2,4,5-tetrazine 在 过氧乙酸 作用下， 以27%的产率得到2,5-bis(4-chlorobenzyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Hunter, Daniel; Neilson, Douglas G.; Weakley, Timothy J.R., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1165 - 1170

  摘要：

  DOI：
• 作为产物：
  描述：

  对氯苯乙腈 在 sulfur 、 溶剂黄146 、 肼 、 sodium nitrite 作用下， 生成 3,6-bis(4-chlorobenzyl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  Synthesis and antitumor activity of s -tetrazine derivatives

  摘要：

  Fifty-five compounds of s-tetrazine derivative including hexahydro-, 1,6-dihydro, 1,4-dihydro-, 1,2-dihydro- and aromatic s-tetrazine were prepared. Their antitumor activities were evaluated in vitro by MTT method for P-388 cell and SRB method for A-549 cell. The results show that there are 9 compounds which in 10(-6) muM have more than 50% inhibition rate to A-549 cancer cell growth, and 7 compounds in 10(-6) muM have more than 50% inhibition rate to P-388 cancer cell growth. The IC50 of compound 3q for P-388, Bel-7402, MCF-7 and A-549 are 0.6 muM, 0.6 muM, 0.5 muM and 0.7 muM, respectively. So s-tetrazine derivative is a kind of compound which possesses potential antitumor activities and is worth to research further. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.056
• 作为试剂：
  描述：

  甲醇 、 3,6-dibenzyl-1,2,4,5-tetrazine 在 氢氧化钾 、 3,6-bis(4-chlorobenzyl)-1,2,4,5-tetrazine 、 air 、 3,6-bis(4-methoxybenzyl)-s-tetrazine 作用下， 生成 3-benzyl-7-methoxy-6-phenyl-imidazo[1,2-b][1,2,4,5]tetrazine 、 3-(4-chlorobenzyl)-6-(4-chlorophenyl)-7-methoxyimidazo<1,2-b>-s-tetrazine 、 7-methoxy-3-(4-methoxybenzyl)-6-(4-methoxyphenyl)imidazo-<1,2-b>-s-tetrazine
  参考文献：
  名称：

  Hunter, Daniel; Neilson, Douglas G.; Weakley, Timothy J.R., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1165 - 1170

  摘要：

  DOI：

文献信息

• Synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions at room temperature
  作者：Zheng Fang、Wen-Li Hu、De-Yong Liu、Chu-Yi Yu、Xiang-Guo Hu

  DOI：10.1039/c6gc03494b

  日期：——

  A procedure for the synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions has been developed.

  已经开发出一种在氧气条件下从gem-二氟烯烃合成四唑的方法。
• Diels–Alder reactions of 3,6-disubstituted 1,2,4,5-tetrazines. Synthesis and X-ray crystal structures of diazafluoranthene derivatives
  作者：Nelli Rahanyan、Anthony Linden、Kim K. Baldridge、Jay S. Siegel

  DOI：10.1039/b820551e

  日期：——

  The synthesis of a series of 3,6-disubstituted-1,2,4,5-tetrazines has been effected using an inverse electron demand [2 + 4] cycloaddition strategy. The crystal structures of 18 members of this series of diazafluoranthenes are reported. Stereochemical analysis shows that diazafluoranthenes, substituted across the bay region, are helically-twisted strained aromatic molecules. The dihedral angle between

  一系列3,6-二取代-1,2,4,5-四嗪的合成已使用反电子需量[2 + 4]环加成策略完成。据报道，该系列二氮杂蒽酮的18个成员的晶体结构。立体化学分析显示，跨海湾区域取代的二氮杂蒽酮是螺旋扭曲的应变芳族分子。哒嗪环与萘基环之间的二面角范围为0.5°至20.9°，并且遵循海湾区域的空间拥挤程度。使用M06-2X / cc-pVDZ方法将晶体结构与使用密度泛函理论确定的计算结构进行比较。
• Synthesis, structures of some unsymmetrical 3,6-disubstituted-1,2,4,5-tetrazines
  作者：Wei-Xiao Hu、Feng Xu

  DOI：10.1002/jhet.5570450628

  日期：2008.11

  A series of new unsymmetrical 3-phenyl-6-benzyl-1,2,4,5-tetrazine derivatives 10a-i were synthesized and characterized by IR, NMR, MS, and element analysis. The structures of 4a, 10c, 10d and 10h were analyzed by X-ray crystallography, which had intermolecular C-H-N, C-H-Cl, C-H-II and II-II interactions.

  合成了一系列新的不对称的3-苯基-6-苄基-1,2,4,5-四嗪衍生物10a-i，并通过IR，NMR，MS和元素分析对其进行了表征。的结构图4a，10C，10D和10H通过X射线晶体学，其具有分子间CHN，CH-CL，CH-II和II-II相互作用分析。
• Hu, Wei-Xiao; Xu, Feng, Journal of Chemical Research, 2006, # 12, p. 797 - 799
  作者：Hu, Wei-Xiao、Xu, Feng

  DOI：——

  日期：——
• Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives
  作者：Guo-Wu Rao、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2006.04.066

  日期：2006.7

  Fourteen compounds of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives were prepared and their structures were confirmed by single-crystal X-ray diffraction and the semi-empirical calculation of PM3 method. This reaction yields the 1,4-dihydro derivatives rather than the 1,2.-dihydro derivatives. The central six-membered ring of 1,4-dihydro-1,2,4,5-tetrazine has a chair conformation and therefore is not homoaromatic. Their antitumor activities were evaluated in vitro by SRB method for A-549 and BEL-7402 cells, and MTT method for P-388 and HL-60 cells. The results show that there is one compound which is highly effective against P-388 cells and one compound which is highly effective against HL-60 cells. So it is a kind of compound which possesses potential antitumor activities and is worth to research further. (c) 2006 Elsevier Ltd. All rights reserved.