1-(3,6-二苯基-1,2,4,5-四嗪-1(4H)-基)乙酮 | 683211-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3,6-二苯基-1,2,4,5-四嗪-1(4H)-基)乙酮
• 英文名称: 1-acetyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine
• 英文别名: 1-(3,6-diphenyl-1H-1,2,4,5-tetrazin-2-yl)ethanone
• CAS: 683211-26-9
• 化学式: C₁₆H₁₄N₄O
• 分子量: 278.313
• InChiKey: IWGHDZZOQHYEID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 1-(3,6-二苯基-1,2,4,5-四嗪-1(4H)-基)乙酮 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以51.5%的产率得到1,4-diacetyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine
  参考文献：
  名称：

  Synthesis, Crystal Structures and Quantum Chemical Calculations of 3,6-diphenyl-1,2-dihydro- and 1,4-dihydro-1,2,4,5-tetrazine derivatives

  摘要：

  1-Acyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazines were prepared by treatment of 3,6-diphenyl-1,4-(or 1,2)-dihydro-1,2,4,5-tetrazine and an equimolar amount of an acyl chloride. Further reaction with another equivalent of an acyl chloride yielded 1,4(or 1,2)-diacyl-3,6-diphenyl-1,4(or 1,2)-dihydro-1,2,4,5-tetrazines. Their structures are confirmed by H-1 NMR, IR, and mass spectra and by elemental analysis and X-ray diffraction. The experimental results are also validated by calculation of molecular stabilisation energies with the DFT calculations (B3LPY method). It can be shown that when alkanoyl chlorides are used, the products are the 1,4-dihydro-1,2,4,5-tetrazines, whereas acylation with aroyl chlorides affords 1,2-dihydro-1,2,4,5-tetrazines.

  DOI：

  10.3184/174751913x13783040292986
• 作为产物：
  描述：

  苯甲腈 在 吡啶 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 一水合肼 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 1-(3,6-二苯基-1,2,4,5-四嗪-1(4H)-基)乙酮
  参考文献：
  名称：

  Synthesis, Crystal Structures and Quantum Chemical Calculations of 3,6-diphenyl-1,2-dihydro- and 1,4-dihydro-1,2,4,5-tetrazine derivatives

  摘要：

  1-Acyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazines were prepared by treatment of 3,6-diphenyl-1,4-(or 1,2)-dihydro-1,2,4,5-tetrazine and an equimolar amount of an acyl chloride. Further reaction with another equivalent of an acyl chloride yielded 1,4(or 1,2)-diacyl-3,6-diphenyl-1,4(or 1,2)-dihydro-1,2,4,5-tetrazines. Their structures are confirmed by H-1 NMR, IR, and mass spectra and by elemental analysis and X-ray diffraction. The experimental results are also validated by calculation of molecular stabilisation energies with the DFT calculations (B3LPY method). It can be shown that when alkanoyl chlorides are used, the products are the 1,4-dihydro-1,2,4,5-tetrazines, whereas acylation with aroyl chlorides affords 1,2-dihydro-1,2,4,5-tetrazines.

  DOI：

  10.3184/174751913x13783040292986

文献信息

• Synthesis and antitumor activity of s -tetrazine derivatives
  作者：Wei-Xiao Hu、Guo-Wu Rao、Ya-Quan Sun

  DOI：10.1016/j.bmcl.2003.12.056

  日期：2004.3

  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.
• Synthesis, X-ray crystallographic analysis, and antitumor activity of 1-acyl-3,6-disubstituted phenyl-1,4-dihydro-1,2,4,5-tetrazines
  作者：Guo-Wu Rao、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2005.03.122

  日期：2005.6

  Eleven compounds of 1-acyl-3,6-disubstituted phenyl-1,4-dihydro-1,2,4,5-tetrazines were prepared from 3,6-disubstituted phenyl-1,2-dihydro-1,2,4,5-tetrazines and anhydrides or acyl chlorines, 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 these compounds has an obvious boat conformation and therefore is not homoaromatic. Their antitumor activities were evaluated in vitro by the SRB method for A-549 cell and the MTT method for P-388 cells. The results show that there is one compound which is highly effective against A-549 cells and two compounds which are highly effective against P-388 cells. Thus, this compound possesses potential antitumor activities and is worth researching further. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and crystal structure of 1-acetyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine
  作者：Guowu Rao、Weixiao Hu

  DOI：10.1023/b:jocc.0000021567.28429.07

  日期：2004.3

  1-Acetyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine ( 1) was prepared and its structure was determined by X-ray diffraction. Crystallization of 1 occurs in the monoclinic space group P2(1)/c with a = 15.180(5) Angstrom, b = 9.216(4) Angstrom, c = 10.129(7) Angstrom; beta = 101.99(5) degrees; and Z = 4. The structure was solved by direct methods and refined to an R value of 0.0414. The central six-membered ring of the compound of 1 has a boat conformation and is not homoaromatic.