3,6-双(4-(三氟甲基)苯基)-1,4-二氢-1,2,4,5-四嗪 | 628732-67-2

• 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: 3,6-双(4-(三氟甲基)苯基)-1,4-二氢-1,2,4,5-四嗪
• 英文名称: 3,6-bis(4-trifluoromethylphenyl)-1,4-dihydro-1,2,4,5-tetrazine
• 英文别名: 3,6-Bis(4-(trifluoromethyl)phenyl)-1,4-dihydro-1,2,4,5-tetrazine；3,6-bis[4-(trifluoromethyl)phenyl]-1,4-dihydro-1,2,4,5-tetrazine
• CAS: 628732-67-2
• 化学式: C₁₆H₁₀F₆N₄
• 分子量: 372.273
• InChiKey: HGHXRUZEVRNFLV-UHFFFAOYSA-N

物化性质

• 沸点：
  372.3±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-双(4-(三氟甲基)苯基)-1,4-二氢-1,2,4,5-四嗪 在 溶剂黄146 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 以24%的产率得到3,6-bis(4-(trifluoromethyl)phenyl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  通过取代吸电子/键合基团的有机电极材料对s-四嗪的氧化还原电位的调节

  摘要：

  在这里，我们通过将各种给电子/吸电子基团（甲氧基，叔丁基，H，F和三氟甲基）引入3,6-二苯基-1,2,4,5-四嗪（DPT）的氧化还原电位它的两个外围苯环用作锂离子电池的电极材料。通过理论DFT计算和实际循环伏安（CV）测量，结果表明1,2,4,5-四嗪（s-tetrazines）的氧化还原电势（E 1/2）与取代基的哈米特常数。在锂离子纽扣电池中，根据取代基的给电子/吸电子能力成功地调节了s-四嗪电极的放电电压。此外，发现异质电子传递速率（k 0s-四嗪分子的电导率和s-四嗪电极中的锂离子扩散率（D Li）比常规电极活性材料快得多。

  DOI：

  10.3390/molecules26040894
• 作为产物：
  描述：

  对三氟甲基苯腈 在 sulfur 、 一水合肼 作用下， 以 乙醇 为溶剂， 以85.5%的产率得到3,6-双(4-(三氟甲基)苯基)-1,4-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  通过取代吸电子/键合基团的有机电极材料对s-四嗪的氧化还原电位的调节

  摘要：

  在这里，我们通过将各种给电子/吸电子基团（甲氧基，叔丁基，H，F和三氟甲基）引入3,6-二苯基-1,2,4,5-四嗪（DPT）的氧化还原电位它的两个外围苯环用作锂离子电池的电极材料。通过理论DFT计算和实际循环伏安（CV）测量，结果表明1,2,4,5-四嗪（s-tetrazines）的氧化还原电势（E 1/2）与取代基的哈米特常数。在锂离子纽扣电池中，根据取代基的给电子/吸电子能力成功地调节了s-四嗪电极的放电电压。此外，发现异质电子传递速率（k 0s-四嗪分子的电导率和s-四嗪电极中的锂离子扩散率（D Li）比常规电极活性材料快得多。

  DOI：

  10.3390/molecules26040894

文献信息

• 3,6-Substituted-1,2,4,5-tetrazines: tuning reaction rates for staged labeling applications
  作者：Danzhu Wang、Weixuan Chen、Yueqin Zheng、Chaofeng Dai、Ke Wang、Bowen Ke、Binghe Wang

  DOI：10.1039/c4ob00280f

  日期：——

  Cycloaddition reactions involving tetrazines have proven to be powerful bioorthogonal tools for various applications. Conceivably, sequential and selective labeling using tetrazine-based reactions can be achieved by tuning the reaction rate. By varying the substituents on tetrazines, cycloaddition rate variations of over 200 fold have been achieved with the same dienophile. Upon coupling with different dienophiles, such as norbornene, the reaction rate difference can be over 14 000 fold. These substituted tetrazines can be very useful for selective labeling under different conditions.

  涉及四氮杂环的环加成反应已被证明是多种应用的强大生物正交工具。可以想象，通过调整反应速率，可以实现基于四氮杂环的顺序和选择性标记。通过改变四氮杂环上的取代基，已实现与相同的二烯亲和体相比超过200倍的环加成速率变化。与不同的二烯亲和体（如诺尔本烯）耦合时，反应速率差异可超过14,000倍。这些取代的四氮杂环在不同条件下的选择性标记中非常有用。
• First representatives of <i>C</i>-glycosyl 1,2,4,5-tetrazines: synthesis of 3-β-<scp>d</scp>-glucopyranosyl 1,2,4,5-tetrazines and their transformation into 3-β-<scp>d</scp>-glucopyranosyl pyridazines
  作者：Éva Bokor、Dóra T. Kecskés、Ferenc Gombás、Alexandra Fehér、Eszter Kardos、Akram Dabian、Zsófia Vonza、Eszter Szennyes、László Somsák

  DOI：10.1039/d2nj03920f

  日期：——

  applications e.g. in heterocyclic syntheses and recently in bioorthogonal chemistry. C-Glycopyranosyl tetrazines are unknown in the literature, therefore, we have started to study their synthesis. In this paper ring closing reactions leading to s-tetrazines have been investigated with suitable β-D-glucopyranosyl precursors and the feasible transformations have been identified. In addition, the obtained

  1,2,4,5-四嗪（s-四嗪）是一类早已为人所知的化合物，具有许多应用，例如杂环合成和最近的生物正交化学。C- Glycopyranosyl四嗪在文献中是未知的，因此，我们已经开始研究它们的合成。在本文中，已经用合适的 β- D-吡喃葡萄糖基前体研究了导致s-四嗪的闭环反应，并确定了可行的转化。此外，获得的C-吡喃葡萄糖基四嗪的基本保护基相容性及其在反电子需求 Diels-Alder 环加成对各种C-吡喃葡萄糖基哒嗪已被证实。
• Synthesis and Crystal Structure of 1-Propionyl-3,6-bis (4-trifluoromethyl-phenyl)-1,4-dihydro-1,2,4,5-tetrazine
  作者：Guo-Wu Rao、Wei-Xiao Hu

  DOI：10.1007/s10870-011-0037-3

  日期：2011.7

  1-Propionyl-3,6-bis(4-trifluoromethyl-phenyl)-1,4-dihydro-1,2,4,5-tetrazine was prepared and its structure was determined by X-ray diffraction. Crystallization occurs in the monoclinic space group P21/c with a = 9.570 (2) Å, b = 12.273 (2) Å, c = 16.641 (3) Å; β = 103.75 (1)°; and Z = 4. The structure was solved by direct methods and refined to an R value of 0.0318. The central six-membered ring of the title compound has a boat conformation and is not homoaromatic.

  1-丙酰基-3,6-双(4-三氟甲基苯基)-1,4-二氢-1,2,4,5-四嗪已制备完成，其结构已通过X射线衍射测定。结晶发生在单斜晶系空间群P21/c中，a=9.570(2)Å，b=12.273(2)Å，c=16.641(3)Å；β=103.75(1)°；Z=4。该结构通过直接方法求解，并精炼至R值为0.0318。标题化合物的中心六元环具有船形构象，且不具有同芳香性。
• 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, structure analysis, antitumor evaluation and 3D-QSAR studies of 3,6-disubstituted-dihydro-1,2,4,5-tetrazine derivatives
  作者：Guo-Wu Rao、Cui Wang、Jian Wang、Zhen-Guo Zhao、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2013.09.036

  日期：2013.12

  3,6-Diaryl-dihydro-1,2,4,5-tetrazine derivatives were synthesized and their structures were confirmed by single-crystal X-ray diffraction. Monosubstituted dihydrotetrazines are the 1,4-dihydro structure, but disubstituted dihydrotetrazines are the 1,2-dihydro structure. The results of further research indicated there may be a rearrangement during the synthesis process of disubstituted dihydrotetrazines. Their antitumor activities were evaluated against A-549 and P388 cells in vitro. The results showed several compounds to be endowed with cytotoxicity in the low micromolar range. Two compounds were highly effective against A-549 cell and IC50 values were 0.575 and 2.08 mu M, respectively. Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were carried out on 37 1,2,4,5-tetrazine derivatives with antitumor activity against A-549 cell. Models with good predictive abilities were generated with the cross validated q(2) values for CoMFA and CoMSIA being 0.744 and 0.757, respectively. Conventional r(2) values were 0.978 and 0.988, respectively, the predicted R-2 values were 0.916 and 0.898, respectively. The results provide the tool for guiding the design and synthesis of novel and more potent tetrazine derivatives. (C) 2013 Elsevier Ltd. All rights reserved.