1,11-bis(1,2,4-triazin-3-ylsulphanyl)-3,6,9-trioxaundecane | 1009834-72-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,11-bis(1,2,4-triazin-3-ylsulphanyl)-3,6,9-trioxaundecane
• 英文别名: 1,11-bis(1,2,4-trizin-3-ylsulfanyl)-3,6,9-trioxaundecane；1,11-bis(1,2,4-triazin-3-ylsulfanyl)-3,6,9-trioxaundecane；1,11-Bis(1,2,4-triazin-3-ylsulphanyl)-3,6,9-trioxaundecane；3-[2-[2-[2-[2-(1,2,4-triazin-3-ylsulfanyl)ethoxy]ethoxy]ethoxy]ethylsulfanyl]-1,2,4-triazine
• CAS: 1009834-72-3
• 化学式: C₁₄H₂₀N₆O₃S₂
• 分子量: 384.483
• InChiKey: JBSQQYSCTAHWSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,11-bis(1,2,4-triazin-3-ylsulphanyl)-3,6,9-trioxaundecane 在 potassium cyanide 作用下， 以 水 为溶剂， 生成 4,7,10-trioxa-1,13-dithia[13](6,6')-2,2'-bis(cyclopenta[c]pyridin-2-yl)cyclophane
  参考文献：
  名称：

  Conformational preferences of thiacrown ethers containing a 5,5′-bi-1,2,4-triazine subunit: X-ray analysis and DFT calculations

  摘要：

  The crystal structure determinations and theoretical calculations at DFT/B3LYP/6-311++G(d,p) level of 5,5'-bi-1,2,4-triazine thiacrown ethers containing 16-, 19- and 22-membered macrocyclic ring were used to analyze their conformational preferences in the crysalline state and gaseous phase.

  DOI：

  10.1515/hc.2010.010
• 作为产物：
  描述：

  1-溴-2-(2-(2-(2-溴乙氧基)乙氧基)乙氧基)乙烷 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 生成 1,11-bis(1,2,4-triazin-3-ylsulphanyl)-3,6,9-trioxaundecane
  参考文献：
  名称：

  通过 5,5'-双-1,2,4-三嗪硫大环化合物的 DA-rDA 反应制备 2,2'-联吡啶基噻冠醚及其亚砜的简便方法。构象研究

  摘要：

  Diels-Alder/retro Diels-Alder (DA-rDA) 反应 5,5'-bi-1,2,4-三嗪硫大环 4a-c 得到中等大小的基于 2,2'-联吡啶的噻冠醚 5a-c良好的产量。后者使用 Davis oxaziridine 被氧化为非外消旋单亚砜 7a-c，并在二乙基锌与苯甲醛的不对称加成中作为手性助剂进行测试。进行了 DFT /B3LYP/6-311G** 水平的理论计算，从而建立了目标硫大环的顺式或反式构象偏好。

  DOI：

  10.3998/ark.5550190.0012.911

文献信息

• Sequential homo-coupling Diels–Alder/retro Diels–Alder reaction of 5,5′-bi-1,2,4-triazine-containing thiamacrocycles as a new route to thiacrown ethers incorporating a 2,2′-bipyridine subunit
  作者：Justyna Ławecka、Ewa Olender、Paweł Piszcz、Andrzej Rykowski

  DOI：10.1016/j.tetlet.2007.11.138

  日期：2008.1

  A new route to thiacrown ethers 5a–d and 6a–d incorporating a 2,2′-bipyridine subunit is elaborated using, (1) homo-coupling of 1,2,4-triazine sulfides 3a–d tethered to poly(ethylene glycol) chains with potassium cyanide and (2) Diels–Alder/retro Diels–Alder reaction with norbornadiene or 1-pyrrolidino-1-cyclopentene as the key steps.

  使用（1）将1,2,4-三嗪硫化物3a - d均系连接到聚乙二醇上，详细阐述了结合有2,2'-联吡啶亚基的硫杂冠醚5a - d和6a - d的新途径）链与氰化钾和（2）与降冰片二烯或1-吡咯烷基-1-环戊烯为主要步骤的狄尔斯-阿尔德/逆狄尔斯-阿尔德反应。
• Anti-oxidative properties of bi-1,2,4-triazine bisulphides
  作者：Paweł Piszcz、Bronisław Głód

  DOI：10.2478/s11696-013-0355-3

  日期：2013.1.1

  The anti-oxidative properties of bitriazines (BTs) were evaluated using HPLC and cyclic voltammetry. In the first case, a RP-HPLC assay was made, using a fluorescence detector, hydroxyl radicals generated in Fenton reaction, and terephthalic acid as a spin trap. The measurements were performed using aqueous or methanolic solutions. It was found that when the BTs were dissolved in water they were antioxidants

  使用高效液相色谱法和循环伏安法评估了比特嗪（BTs）的抗氧化性能。在第一种情况下，使用荧光检测器，在Fenton反应中产生的羟基自由基和对苯二甲酸作为自旋阱，进行RP-HPLC分析。使用水溶液或甲醇溶液进行测量。发现当BT溶解在水中时它们是抗氧化剂，而溶解在甲醇中它们是前氧化剂。通过伏安法，色谱法和分光光度法测定，证实了它们在两种溶剂中的不同理化性质。
• A Convenient Approach to 16-, 19-, and 22-Membered 2,2′-Bipyridine Thiacrown Ethers and Their Conformation Preferences
  作者：Justyna Ławecka、Zbigniew Karczmarzyk、Ewa Wolińska、Danuta Branowska、Andrzej Rykowski

  DOI：10.1002/ejoc.201000590

  日期：2010.9

  of 1:1 thiacrown ether macrocycles 5a―c containing a fused cyclopenteno[c]2,2'-bipyridine subunit has been accomplished through first homo-coupling of 1,2,4-triazine bisulfides 3a―c tethered to poly(ethylene glycol) chains with potassium cyanide and second Diels―Alder/retro-Diels―Alder reaction of such obtained thiamacrocycles 4a―c with 1-pyrrolidino-1-cyclopentene. Macrocycles 5a―c were oxidized to

  通过 1,2,4-三嗪二硫化物 3a- 的第一次均偶联，完成了含有稠合环戊烯 [c]2,2'-联吡啶亚基的 1:1 硫冠醚大环 5a-c 的方便的三步合成c 用氰化钾和第二个 Diels-Alder/retro-Diels-Alder 反应连接到聚（乙二醇）链上，这样获得的硫大环 4a-c 与 1-吡咯烷基-1-环戊烯。大环 5a-c 被氧化成非外消旋单亚砜 6a-c 通过使用戴维斯的恶氮丙啶，并在二乙基锌与苯甲醛的不对称加成中进行测试。5a-c和6b的晶体结构测定和DFT/B3LYP/6-311G"水平的理论计算被用来确定它们在固态和气相中的顺式或反式构象。
• A facile approach to 2,2′-bipyridine based thiacrown ethers and their sulfoxides by DA-rDA reaction of 5,5′-bi-1,2,4-triazine thiamacrocycles. The conformation studies
  作者：Justyna Ławecka、Zbigniew Karczmarzyk、Ewa Olender、Ewa Wolińska、Danuta Branowska、Andrzej Rykowski

  DOI：10.3998/ark.5550190.0012.911

  日期：——

  Diels-Alder/retro Diels-Alder (DA-rDA) reactions of 5,5′-bi-1,2,4-triazine thiamacrocycles 4a–c afforded medium-size 2,2′-bipyridine based thiacrown ethers 5a–c in good yield. The latter were oxidized to non-racemic monosulfoxides 7a–c using Davis oxaziridine and tested as chiral auxilaries in the asymmetric addition of diethyl zinc to benzaldehyde. The theoretical calculations at DFT /B3LYP/6-311G**

  Diels-Alder/retro Diels-Alder (DA-rDA) 反应 5,5'-bi-1,2,4-三嗪硫大环 4a-c 得到中等大小的基于 2,2'-联吡啶的噻冠醚 5a-c良好的产量。后者使用 Davis oxaziridine 被氧化为非外消旋单亚砜 7a-c，并在二乙基锌与苯甲醛的不对称加成中作为手性助剂进行测试。进行了 DFT /B3LYP/6-311G** 水平的理论计算，从而建立了目标硫大环的顺式或反式构象偏好。
• Conformational preferences of thiacrown ethers containing a 5,5′-bi-1,2,4-triazine subunit: X-ray analysis and DFT calculations
  作者：Zbigniew Karczmarzyk、Ewa Wolińska、Justyna Ławecka、Monika Cyrta、Andrzej Rykowski

  DOI：10.1515/hc.2010.010

  日期：2010.1.1

  The crystal structure determinations and theoretical calculations at DFT/B3LYP/6-311++G(d,p) level of 5,5'-bi-1,2,4-triazine thiacrown ethers containing 16-, 19- and 22-membered macrocyclic ring were used to analyze their conformational preferences in the crysalline state and gaseous phase.