3,3'-selenobispyridine | 142208-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,3'-selenobispyridine
• 英文别名: 3-Pyridylselenide；3-pyridin-3-ylselanylpyridine
• CAS: 142208-94-4
• 化学式: C₁₀H₈N₂Se
• 分子量: 235.147
• InChiKey: AYRCABFDTIVFKT-UHFFFAOYSA-N

物化性质

• 沸点：
  351.8±17.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.13
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-碘吡啶 在 copper(l) iodide 、 (1R,2R)-1,2-diaminocyclohexane 、 水 、 potassium selenocyanate 、 caesium carbonate 作用下， 反应 24.0h， 以74%的产率得到3,3'-selenobispyridine
  参考文献：
  名称：

  硒氰化钾是水中碘化铜催化C-Se交叉偶联的有效硒源

  摘要：

  在水中已开发出一种有效且概念上新颖的方案，用于通过铜催化的级联反应将硒氰酸钾与芳基卤化物进行C-Se交叉偶联。利用该方案，使各种芳基和杂芳基卤化物与硒氰酸钾反应，以中等至良好的产率得到相应的二芳基硒化物。

  DOI：

  10.1016/j.tetlet.2011.05.068

文献信息

• Nano Copper Oxide Catalyzed Synthesis of Symmetrical Diaryl Selenides via Cascade Reaction of KSeCN with Aryl Halides
  作者：Y. Nageswar、K. Reddy、V. Reddy、B. Madhav、J. Shankar

  DOI：10.1055/s-0030-1260553

  日期：2011.6

  An unprecedented transfer of selenium ion from potassium selenocyanate was observed in C-Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand-free conditions. Utilizing this protocol wide range of symmetrical diaryl selenides were obtained in excellent yields. Nano-CuO is recyclable up to four cycles without loss of catalytic activity.

  在无配体条件下，铜氧化物纳米颗粒催化C-Se交叉偶联反应中观察到前所未有的硒离子来自亚硒酸钾的转移现象。利用这一方法，成功获得了广泛的对称二芳基硒化合物，并且产率极佳。纳米CuO具有可循环使用四次的特性，且不会损失催化活性。
• Palladium Nanoparticles Supported on Nitrogen-rich Containing Melamine-based Microporous Covalent Triazine Polymers as Efficient Heterogeneous Catalyst for C−Se Coupling Reactions
  作者：Velu Sadhasivam、Rajendiran Balasaravanan、Chinnadurai Chithiraikumar、Ayyanar Siva

  DOI：10.1002/cctc.201800400

  日期：2018.9.7

  present work, microporous nitrogen containing covalent triazine polymers (CTPs) TATAM was synthesized from condensation of 4,4′4′′‐(1,3,5‐triazine‐2,4,6‐triyl) tribenzaldehyde (TATA) and melamine under solvothermal conditions to obtain nitrogen‐ rich triazine containing polymeric supported materials (TATAM). Further, palladium nanoparticles (Pd NPs) were supported on TATAM polymeric networks (Pd@TATAM).

  在目前的工作中，由4,4'4''-（1,3,5-triazine-2,4,6-三基）三苯甲醛（TATA）与在溶剂热条件下获得三聚氰胺，以获得富含氮的含三嗪的聚合物载体材料（TATAM）。此外，钯纳米颗粒（Pd NPS）被支撑在TATAM聚合物网络（Pd @ TATAM）上。合成的Pd @ TATAM CTPs材料通过FT-IR，UV-DRS，固态13进行了彻底表征C‐CPMAS，XPS，粉末X射线衍射，TGA，SEM，TEM。此外，将表征的Pd @ TATAM CTP用于检查催化应用。Pd @ TATAM被证明是一种有效且可重复使用的非均相固体催化剂，可通过在100°C下将芳基卤化物和元素硒，二甲基亚砜作为溶剂偶联形成C-SE键约6 h。除了不存在用于催化体系的金属浸出外，还观察到该催化剂可以连续三个循环重复使用，其活性降低最小。
• Unexpected C−Se Cross-Coupling Reaction: Copper Oxide Catalyzed Synthesis of Symmetrical Diaryl Selenides via Cascade Reaction of Selenourea with Aryl Halides/Boronic Acids
  作者：V. Prakash Reddy、A. Vijay Kumar、K. Rama Rao

  DOI：10.1021/jo102017g

  日期：2010.12.17

  Selenourea is used as an effective selenium surrogate in the C−Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand free conditions. This protocol has been utilized for the synthesis of a variety of symmetrical diaryl selenides in good to excellent yields from the readily available aryl halides/boronic acids.

  在无配体条件下，氧化铜纳米粒子催化的硒化硒在C-Se交叉偶联反应中用作有效的硒替代物。该方案已被用于从容易获得的芳基卤化物/硼酸以良好或优异的产率合成多种对称的二芳基硒化物。
• Selenacalix[4]dithienothiophene: Synthesis, Structure, and Complexation of a Cyclic Tetramer of Selenide‐Bridging Dithienothiophene
  作者：Masashi Hasegawa、Kazuhiro Takahashi、Ryota Inoue、Shiori Haga、Yasuhiro Mazaki

  DOI：10.1002/asia.201801105

  日期：2019.5.15

  An efficient cyclization toward a cyclic tetramer of dithienothiophene (DTT) linked by divalent selenium atoms has been developed via palladium‐catalyzed coupling reaction of (nBu3Sn)2Se. X‐ray analysis revealed its highly symmetrical structure had an alternate arrangement of DTT units. There are several Se⋅⋅⋅π interactions forming a supramolecular network leading to large void channel space. The cyclic

  通过（n Bu 3 Sn）2 Se的钯催化偶联反应，已经开发出了有效的环化成环二硫噻吩（DTT）的环四聚体，该环四噻吩通过二价硒原子连接。X射线分析显示其高度对称的结构具有DTT单元的替代排列。有多个Se⋅⋅⋅ππ相互作用形成超分子网络，从而导致大的空隙通道空间。环状四聚体具有中等的供电子能力。此外，环状四聚体在固态下以1：2的比例与C 60络合，形成高度对称的C 60三维阵列。
• Microwave-assisted Cu2O-catalyzed one-pot synthesis of symmetrical diaryl selenides from elemental selenium
  作者：Shaozhong Zhang、Kranthi Karra、Christina Heintz、Erica Kleckler、Jin Jin

  DOI：10.1016/j.tetlet.2013.06.117

  日期：2013.8

  A novel and simple microwave-assisted one-pot protocol to prepare symmetrical diary] selenides has been developed. A cross-coupling reaction between aryl iodide and elemental selenium takes place in the presence of KOH and a catalytic amount of Cu2O/NH2CH2CH2NH2, leading to C-Se bond formation. The reactions are highly efficient with a reaction time of 1 h under microwave irradiation and yields from 50% to 90%. Published by Elsevier Ltd.