(E)-2-(4-octen-4-yl)-5-phenyl-1,3,4-oxadiazole | 1181218-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(4-octen-4-yl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: (E)-5-phenyl-2-(4-octen-4-yl)-1,3,4-oxadiazole；2-[(E)-oct-4-en-4-yl]-5-phenyl-1,3,4-oxadiazole
• CAS: 1181218-99-4
• 化学式: C₁₆H₂₀N₂O
• 分子量: 256.348
• InChiKey: AUMFXWWWQXPKEU-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基-1,3,4-噁二唑 、 4-辛炔 在 吡啶 、 (三甲基硅基)甲基氯化镁 、 双(2-二苯基磷苯基)醚 、 cobalt(II) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到(E)-2-(4-octen-4-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Cobalt-Catalyzed Addition of Azoles to Alkynes

  摘要：

  A ternary catalytic system consisting of a cobalt salt, a diphosphine ligand, and a Grignard reagent promotes syn-addition of an azole C(2)-H bond across an unactivated internal alkyne with high chemo-, regio-, and stereoselectivities under mild conditions. Mechanistic experiments suggest that the reaction involves oxidative addition of the oxazolyl C-H bond to the cobalt center, alkyne insertion into the Co-H bond, and reductive elimination of the resulting diorganocobalt species.

  DOI：

  10.1021/ol101777x

文献信息

• Nickel-Catalyzed C−H Alkenylation and Alkylation of 1,3,4-Oxadiazoles with Alkynes and Styrenes
  作者：Tomoya Mukai、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo901350j

  日期：2009.8.21

  The addition reaction of 1,3,4-oxadiazoles to alkynes via C-H bond cleavage efficiently proceeds in the presence of a nickel catalyst. This direct coupling allows a facile access to alkenyl-substituted oxadiazoles. The reaction with styrenes in place of alkynes is also available to selectively afford the corresponding branched adducts.
• Cobalt-Catalyzed Addition of Azoles to Alkynes
  作者：Zhenhua Ding、Naohiko Yoshikai

  DOI：10.1021/ol101777x

  日期：2010.9.17

  A ternary catalytic system consisting of a cobalt salt, a diphosphine ligand, and a Grignard reagent promotes syn-addition of an azole C(2)-H bond across an unactivated internal alkyne with high chemo-, regio-, and stereoselectivities under mild conditions. Mechanistic experiments suggest that the reaction involves oxidative addition of the oxazolyl C-H bond to the cobalt center, alkyne insertion into the Co-H bond, and reductive elimination of the resulting diorganocobalt species.