2-butylselenobenzothiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-butylselenobenzothiazole
• 英文别名: 2-Butylselanyl-1,3-benzothiazole
• 化学式: C₁₁H₁₃NSSe
• 分子量: 270.257
• InChiKey: HVIFKBQJMLHFTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯硼酸 、 2-butylselenobenzothiazole 在 四(三苯基膦)钯 、 copper(II) acetate monohydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以32%的产率得到2-(4-甲氧苯基)苯并噻唑
  参考文献：
  名称：

  Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions

  摘要：

  通过钯催化的不饱和有机硒化合物交叉偶联反应，构建新的碳-碳键的强大工具被描述。

  DOI：

  10.1039/c5cc06347g
• 作为产物：
  描述：

  苯并噻唑 、 二丁基二硒醚 在 copper(II) oxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到2-butylselenobenzothiazole
  参考文献：
  名称：

  噻唑中碳氢键的氧化铜纳米粒子催化硫属元素化：2-（有机碳烷氧基）噻唑的合成

  摘要：

  AbstractWe present (homepage: www.ufsm.br) herein the application of copper nanoparticles/diorganyl dichalcogenides to promote the synthesis of 2‐(organochalcogen)thiazoles via direct carbon‐hydrogen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron‐donating and electron‐withdrawing substituents, in the aromatic ring bonded to the chalcogen atom of diorganyl dichalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.magnified image

  DOI：

  10.1002/adsc.201300497

文献信息

• Preparation of 2-(Alkylseleno)benzothiazoles. Direct Incorporation of the Alkyl Group of Alcohols into Benzothiazolylseleno Residue
  作者：Koichi Shibata、Oyo Mitsunobu

  DOI：10.1246/cl.1993.549

  日期：1993.3

  Reaction of alcohols with 2-(1,2-diphenyl-2-oxoethylseleno)benzothiazole in the presence of tributylphosphine gave the corresponding 2-alkylselenobenzothiazoles, where inversion of the secondary carbinol center of the alcohols took place. 1,3-Butanediol reacted at the primary hydroxyl group, while 1-phenyl-1,2-ethanediol reacted at the secondary hydroxyl group.

  在三丁基膦存在下，醇与2-(1,2-二苯基-2-氧乙硒基)苯并噻唑反应，生成相应的2-烷基硒基苯并噻唑，其中醇的二级羟甲基中心发生了构型反转。1,3-丁二醇在伯羟基处反应，而1-苯基-1,2-乙二醇在仲羟基处反应。
• Preparation of 2-Alkylselenobenzothiazoles by the Reaction of Alcohols with 2-(2-Oxoethylseleno)benzothiazoles in the Presence of Tertiary Phosphines
  作者：Ohyo Mitsunobu、Koichi Shibata、Hiko Yamaga

  DOI：10.3987/com-98-s(h)94

  日期：——
• Copper Oxide Nanoparticle-Catalyzed Chalcogenation of the Carbon-Hydrogen Bond in Thiazoles: Synthesis of 2-(Organochalcogen)thiazoles
  作者：Alisson R. Rosario、Kamila K. Casola、Carla E. S. Oliveira、Gilson Zeni

  DOI：10.1002/adsc.201300497

  日期：2013.10.11

  AbstractWe present (homepage: www.ufsm.br) herein the application of copper nanoparticles/diorganyl dichalcogenides to promote the synthesis of 2‐(organochalcogen)thiazoles via direct carbon‐hydrogen bond activation in thiazoles. A systematic study of the catalytic system revealed that the presence and amount of base played an essential role in this reaction. The results revealed that electron‐donating and electron‐withdrawing substituents, in the aromatic ring bonded to the chalcogen atom of diorganyl dichalcogenides, required one equiv. of base, while when neutral substituents were present two equiv. of base were needed to deliver the products in similar yields.magnified image
• Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions
  作者：A. L. Stein、F. N. Bilheri、G. Zeni

  DOI：10.1039/c5cc06347g

  日期：——

  A powerful tool for constructing new carbon–carbon bonds via palladium-catalyzed cross-coupling reactions of unsaturated organoselenides is described.

  通过钯催化的不饱和有机硒化合物交叉偶联反应，构建新的碳-碳键的强大工具被描述。