1-(3,6-二苯基-1,2,4,5-四嗪-1(4H)-基)丙烷-1-酮 | 861387-33-9

• 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)丙烷-1-酮
• 英文名称: 1-propionyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine
• 英文别名: 1-(3,6-Diphenyl-1,2,4,5-tetrazin-1(2H)-yl)propan-1-one；1-(3,6-diphenyl-1H-1,2,4,5-tetrazin-2-yl)propan-1-one
• CAS: 861387-33-9
• 化学式: C₁₇H₁₆N₄O
• 分子量: 292.34
• InChiKey: WSUDOHGQNAWKGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  145 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  420.7±28.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-(3,6-二苯基-1,2,4,5-四嗪-1(4H)-基)丙烷-1-酮 、 丙酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以41.3%的产率得到1,4-propionyl-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)丙烷-1-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 Structure Analysis of 1-propionyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine
  作者：Guo-Wu Rao、Jia-Bin Ni、Yu-Bo Fu、Hao Chen

  DOI：10.3184/174751913x13626783814049

  日期：2013.4

  1-Propionyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine was prepared from propionic anhydride and 3,6-diphenyl-1,4(or 1,2)-dihydro-1,2,4,5-tetrazine, and its structure was determined by X-ray diffraction. This reaction yields the title compound rather than 1-propionyl-3,6-diphenyl-1,2-dihydro-1,2,4,5-tetrazine. The central tetrazine ring of the title compound exhibits a boat conformation and is not, therefore, homoaromatic.

  由丙酸酐和 3,6-二苯基-1,4（或 1,2）-二氢-1,2,4,5-四嗪制备了 1-丙酰基-3,6-二苯基-1,4-二氢-1,2,4,5-四嗪，并通过 X 射线衍射测定了其结构。该反应生成的是标题化合物，而不是 1-丙酰基-3,6-二苯基-1,2-二氢-1,2,4,5-四嗪。标题化合物的中心四嗪环呈现舟形构象，因此不是同芳香族。
• 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, Crystal Structures and Quantum Chemical Calculations of 3,6-diphenyl-1,2-dihydro- and 1,4-dihydro-1,2,4,5-tetrazine derivatives
  作者：Zhen-Zhen Yang、Feng Xu、Zhong-Lu Ke、Hong-Yun Chen、Wei-Xiao Hu、Hai-Bo Li

  DOI：10.3184/174751913x13783040292986

  日期：2013.10

  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.