3,6-bis-(4-chloro-phenyl)-[1,2,4,5]tetrazine | 37932-45-9

• 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-chloro-phenyl)-[1,2,4,5]tetrazine
• 英文别名: 3,6-bis(4-chlorophenyl)-1,2,4,5-tetrazine；3,6-bis-(4-chlorophenyl)-s-tetrazine；3,6-bis(p-chlorophenyl)-1,2,4,5-tetrazine；3,6-Bis-(p-chlor-phenyl)-1,2,4,5-tetrazin；3,6-Bis(4-chlorphenyl)-sym-tetrazin；3,6-Bis-(p-chlorphenyl)-s-tetrazin
• CAS: 37932-45-9
• 化学式: C₁₄H₈Cl₂N₄
• mdl: MFCD01117383
• 分子量: 303.15
• InChiKey: OCLIQMAKECCZNO-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C(Solv: ethanol (64-17-5))
• 沸点：
  488.5±55.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  cyclopropene 、 3,6-bis-(4-chloro-phenyl)-[1,2,4,5]tetrazine 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到2,5-bis(p-chlorophenyl)-3,4-diazanorcaradiene
  参考文献：
  名称：

  [4+2] 1,2,4,5-四嗪和环丙烯的环加成 - 3,4-二氮杂降碳二烯和四环脂肪族偶氮化合物的合成

  摘要：

  1,2,4,5-四嗪 1 容易与环丙烯 2 反应以在环加成 - 环消除序列中形成 3,4-二氮杂二氮杂环二烯 3、4、7 和 8。化合物 3 和 4 仍然与环丙烯 2 一起作为 1,3-二烯，产生脂肪族偶氮化合物 5 和 6，这是热解和光解反应中的通用起始化合物。

  DOI：

  10.1002/1099-0690(200107)2001:14<2629::aid-ejoc2629>3.0.co;2-2
• 作为产物：
  描述：

  3,6-二(4-氯苯基)-1,2-二氢-1,2,4,5-四嗪 在 溶剂黄146 、 sodium nitrite 作用下， 以87%的产率得到3,6-bis-(4-chloro-phenyl)-[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

文献信息

• Novel synthesis of 3,6-disubstituted-1,2,4,5-tetrazine derivatives from hydrazones by using [hydroxyl(tosyloxy)iodo]benzene
  作者：Haixuan Liu、Yunyang Wei

  DOI：10.1016/j.tetlet.2013.06.053

  日期：2013.8

  A mild and efficient protocol for the construction of 1,4-dihydro-3,6-disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines from p-toluenesulfonyl hydrazones mediated by [hydroxyl(tosyloxy)iodo]benzene in the presence of pyridine has been developed. This protocol affords the products in good to excellent yields. The corresponding 3,6-disubstituted-1,2,4,5-tetrazines can be easily obtained through

  温和和有效的协议的1,4-二氢-3,6-二取代-1,4-双（施工p甲苯磺酰）从-1,2,4,5-四嗪p甲苯磺酰腙由[羟基介导的已经开发了在吡啶存在下的（甲苯磺酰氧基）碘]苯。该协议以良好的产量提供了优良的产品。通过对甲苯磺酰基的一步N-脱保护和在THF中用四丁基氟化铵进行芳构化，可以轻松获得相应的3,6-二取代-1,2,4,5-四嗪。已经提出了一种机制。
• 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。
• Termal rearrangement of 1-alkyl-3,6-diaryl-1,4-dihydro-s-tetrazines to 1-alkylamino-3,5-diaryl-1,2,4-triazoles
  作者：Daniel Hunter、Douglas G. Neilson

  DOI：10.1039/p19840002779

  日期：——

  having aryl substituents in either the 3- or 3,6-positions react readily with alkyl or aryl Grignard reagents to give 1-alkyl (or aryl)-1,4-dihydro-s-tetrazines. The 1-alkyl-1,4-dihydro-s-tetrazines rearrange in methanolic hydrogen chloride to 4-alkylamino-1,2,4-triazoles, but thermolyse readily to the less well known, isomeric 1-alkylamino-1,2,4-triazoles. Possible reaction pathways involving breakdown

  小号具有无论是在3-或3,6-位上有烷基很容易反应或芳基格氏试剂芳基取代基-Tetrazines，得到1-烷基（或芳基）-1,4-二氢-小号-tetrazines。的1-烷基-1,4-二氢-小号-tetrazines重新排列甲醇氯化氢〜4 -烷基氨基-1,2,4-三唑，但thermolyse容易向较公知的，异构体的1-烷基氨基-1,2， 4-三唑。讨论了可能的反应途径，包括分解为腈和反应性中间体（例如1,3-偶极物质）。
• One-step synthesis of benzo[ g ]phthalazines and naphtho[2,3- g ]phthalazines from benzo- or naphtho-oxabicyclic alkene
  作者：Kundi Kong、Jie Zhang、Peng Zhao、Huali Lu、Zhijun Chen、Weiguo Cao、Jie Chen、Yali Chen

  DOI：10.1016/j.tet.2017.10.028

  日期：2017.11

  An efficient protocol for one-step synthesis of oxadisilole-fused benzo[g]phthalazines and naphtho[2,3-g]phthalazines by the Diels-Alder reactions and denitrogenation/deoxygenation aromatization reactions of benzo- or naphtho-oxabicyclic alkene with 3,6-diaryl-1,2,4,5-tetrazines in THF at room temperature for 3 h. The photophysical, redox, and thermal properties of these compounds have been determined

  对于oxadisilole稠合的苯并一步法合成的高效的协议[克]酞嗪和萘并[2,3-克]由苯并或萘并oxabicyclic烯烃与3的狄尔斯-阿尔德反应和脱氮/脱氧芳构化反应酞，室温下于THF中的6-二芳基-1,2,4,5-四嗪3小时。已经确定了这些化合物的光物理性质，氧化还原性质和热性质。还对提出的机制进行了研究。
• Brominated flame-retardant tetrazines
  申请人：International Business Machines Corporation

  公开号：US11198818B2

  公开（公告）日：2021-12-14

  A flame-retardant compound, a process for forming a flame-retardant compound, and an article of manufacture. The flame-retardant compound includes a tetrazine moiety and at least one ligand comprising a brominated moiety. The process includes providing starting materials, which include a nitrile compound, a bromine source, and hydrazine. The process also includes reacting the starting materials to form a tetrazine flame retardant. The article of manufacture includes a polymer and a flame-retardant compound having a tetrazine moiety and at least one ligand comprising a brominated moiety.

  一种阻燃化合物、制造阻燃化合物的工艺以及制造物。所述阻燃化合物包括四嗪基团和至少一个包含溴化基团的配体。所述工艺包括提供起始材料，所述起始材料包括腈类化合物、溴源和水合肼。所述工艺还包括使所述起始材料反应以形成四嗪类阻燃剂。所述制造物包括聚合物和一种阻燃化合物，所述阻燃化合物具有四嗪基团和至少一个包含溴化基团的配体。