3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪 | 74115-15-4

• 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(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪
• 英文名称: 3,6-bis(2-chlorophenyl)-1,2-dihydro-1,2,4,5-tetrazine
• 英文别名: 3,6-bis(2-chlorophenyl)-1,4-dihydro-1,2,4,5-tetrazine
• CAS: 74115-15-4
• 化学式: C₁₄H₁₀Cl₂N₄
• 分子量: 305.166
• InChiKey: DMOSPPXFAKVBOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C(Solv: ethanol (64-17-5))
• 沸点：
  426.6±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)
• 溶解度：
  溶于乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

制备方法与用途

化学性质
3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪纯品为黄色晶体，熔点范围为221～223℃，微溶于甲苯、二氯甲烷和二氯乙烷等有机溶剂。

用途
3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪是制备杀螨剂四螨嗪的重要中间体。

生产方法
3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪是由双(α,2-二氯亚苄基)肼和水合肼反应制得。具体步骤如下：在500 L的反应釜中依次加入甲苯260 L、双(α,2-二氯亚苄基)肼85 kg、碳酸钠28 kg以及1.5 kg相转移催化剂，然后升温至78℃。接着滴加水合肼25.5 kg，滴加完毕后保温1小时。反应结束后进行减压蒸馏，回收甲苯供循环使用；残留物用水洗涤后放入离心机甩滤，滤饼即为3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪。滤液分层，水相送至废水处理工段，油相则进行焚烧处理。

反应信息

• 作为反应物：
  描述：

  3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 5.0h， 以76%的产率得到四螨嗪
  参考文献：
  名称：

  一种四螨嗪的制备方法

  摘要：

  本发明公开了一种四螨嗪的制备方法，以对邻氯苯甲腈为原料，在优选催化剂后，与水合肼一步法直接成环合成二氢四嗪，再将合成的二氢四嗪经过亚钠、盐酸体系氧化后直接合成四螨嗪；得到的四螨嗪纯度≥98％，总收率达到70％以上，与目前现有的技术相比，本工艺路线简单，步骤少，安全程度高，符合目前清洁化生产，安全工业生产的需求。

  公开号：

  CN114163392A
• 作为产物：
  描述：

  邻氯苯腈 在 palladium diacetate 、 一水合肼 、 三对苯甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 3,6-双(2-氯苯基)-1,2-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  一种四螨嗪的制备方法

  摘要：

  本发明公开了一种四螨嗪的制备方法，以对邻氯苯甲腈为原料，在优选催化剂后，与水合肼一步法直接成环合成二氢四嗪，再将合成的二氢四嗪经过亚钠、盐酸体系氧化后直接合成四螨嗪；得到的四螨嗪纯度≥98％，总收率达到70％以上，与目前现有的技术相比，本工艺路线简单，步骤少，安全程度高，符合目前清洁化生产，安全工业生产的需求。

  公开号：

  CN114163392A

文献信息

• [EN] PROCESS FOR PREPARING FUNCTIONALIZED 1,2,4,5-TETRAZINE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS 1,2,4,5-TÉTRAZINE FONCTIONNALISÉS
  申请人：UNIV BOURGOGNE

  公开号：WO2017093263A1

  公开（公告）日：2017-06-08

  The present invention relates to a process for the synthesis of 3,6 functionalized 1,2,4,5-tetrazine compounds of formula (I); wherein A and B being the same; and wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a halogen atom or acetate group; said process comprising reacting the corresponding 1,2,4,5-tetrazine compounds wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a hydrogen atom with an oxidative reagent in presence of a catalyst.

  本发明涉及一种合成式(I)的3,6官能化1,2,4,5-四唑化合物的方法；其中A和B相同；并且其中R1、R1'、R2和R2'中至少一个以及R10和R10'中至少一个是卤素原子或乙酸酯基；所述方法包括在催化剂存在下，将相应的1,2,4,5-四唑化合物与至少一个R1、R1'、R2和R2'中至少一个以及R10和R10'中至少一个是氢原子的氧化试剂发生反应。
• Acaricidal, larvicidal and ovicidal tetrazine derivatives and compositions, processes for their preparation and methods of using them
  申请人：FBC LIMITED

  公开号：EP0005912A1

  公开（公告）日：1979-12-12

  The substituted tetrazines of the formula: and of the formula: wherein: R1, R2 and R4 each represent hydrogen, phenyl, alkyl of 1 to 6 carbon atoms, or alkenyl or alkynyl of 3 to 6 carbon atoms, each of which may be unsubstituted or substituted by one or more halogen atoms, hydroxy groups, cyano groups, carboxy groups, alkoxycarbonyl groups of 2 to 5 carbon atoms, or alkoxy groups of 1 to 4 carbon atoms; or R1 and R2 together represent a single bond; R3 represents alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl, or phenylalkyl of 7 to 10 carbon atoms, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy groups of 1 to 6 carbon atoms, nitro groups, cyano groups, mercapto groups, or alkyl-mercapto groups of 1 to 4 carbon atoms; and R6 represents a phenyl group substituted in at least the 2-position by fluorine, chlorine,. bromine or iodine; are effective to combat acarids and their eggs. Most of the compounds are new and processes for their preparation are described.

  式的取代四嗪： 和式 其中R1、R2 和 R4 各自代表氢、苯基、1 至 6 个碳原子的烷基或 3 至 6 个碳原子的烯基或炔基，其中每个基团可以未被取代或被一个或多个卤素原子、羟基、氰基、羧基、2 至 5 个碳原子的烷氧羰基或 1 至 4 个碳原子的烷氧基取代；或 R1 和 R2 一起代表单键；R3 代表 1 至 6 个碳原子的烷基、3 至 7 个碳原子的环烷基、苯基或 7 至 10 个碳原子的苯基烷基，其中每个烷基可以未被取代，也可以被一个或多个卤素原子、1 至 6 个碳原子的烷基或烷氧基、硝基、氰基、巯基或 1 至 4 个碳原子的烷基-巯基取代；以及 R6 代表至少在 2 位被氟、氯、溴或碘取代的苯基。溴或碘取代的苯基；可有效防治螨虫及其虫卵。 大多数化合物都是新化合物，并介绍了其制备过程。
• ——
  作者：

  DOI：——

  日期：——
• 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, 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.