(E)-2-phenyl-1-(2-pyridyl)-1-pentene-3-one

• 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-phenyl-1-(2-pyridyl)-1-pentene-3-one
• 英文别名: (E)-2-phenyl-1-pyridin-2-ylpent-1-en-3-one
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: SIKWPUUJHQUDFL-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-phenyl-1-(2-pyridyl)-1-pentene-3-one 、 乙二胺 以57%的产率得到
  参考文献：
  名称：

  HANKOVSZKY V. H.; HIDEG K.; LLOYD D.; MCNAB H., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 5, 1345-1350

  摘要：

  DOI：
• 作为产物：
  描述：

  乙烯 、 一氧化碳 、 2-[(E)-2-phenylethenyl]pyridine 在 十二羰基三钌 作用下， 以 甲苯 为溶剂， 140.0 ℃ 、2.03 MPa 条件下， 反应 5.0h， 以0%的产率得到2-Phenyl-1-pyridin-2-ylpentan-3-one
  参考文献：
  名称：

  Ru₃(CO)₁₂- and Rh₄(CO)₁₂-Catalyzed Reactions of Pyridylolefins or N-(2-Pyridyl)enamines with CO and Olefins. Carbonylation at Olefinic C−H Bonds

  摘要：

  This paper describes a study of the Ru-3(CO)(12)-catalyzed carbonylation at an olefinic C-K bond. The reaction of pyridylolefins with CO and ethylene in the presence of a catalytic amount of Ru-3(CO)(12) in toluene results in propionylation at an olefinic C-H bond in pyridylolefins. The carbonylation occurs regioselectively ata position gamma to the pyridine nitrogen. Transition-metal complexes other than Ru3(CO)12 that have thus far been examined exhibit no catalytic activity, and ethylene serves as the only olefin. A similar tendency has been noted in the previously reported carbonylation at a C-H bond in the benzene ring of pyridylbenzenes. This reaction can be also applied to N-(2-pyridyl)enamines, in which an olefin unit is separated from the pyridine ring by an sp(3)-nitrogen atom. The reaction of N-(2-pyridyl)enamines with CO and ethylene gives the corresponding ethyl ketones as the coupling products. Interestingly, Rh-4(CO)(12) also shows high catalytic activity in the case of N-(2-pyridyl)enamines. In addition, olefins such as propene, 1-hexene, 3,3-dimethyl-1-butene, styrene, cyclopentene, acryl acid methyl ester, ethyl vinyl ether, and trimethylvinylsilane can also be used. This is in sharp contrast to the case of the carbonylation at a C-H bond in pyridylbenzenes reported previously and to the results of pyridylolefins as mentioned above, where Ru-3(CO)(12) is the only active catalyst and hexene-cannot substitute for ethylene.

  DOI：

  10.1021/jo980335n

文献信息

• Ru₃(CO)₁₂- and Rh₄(CO)₁₂-Catalyzed Reactions of Pyridylolefins or <i>N</i>-(2-Pyridyl)enamines with CO and Olefins. Carbonylation at Olefinic C−H Bonds
  作者：Naoto Chatani、Yutaka Ishii、Yutaka Ie、Fumitoshi Kakiuchi、Shinji Murai

  DOI：10.1021/jo980335n

  日期：1998.7.1

  This paper describes a study of the Ru-3(CO)(12)-catalyzed carbonylation at an olefinic C-K bond. The reaction of pyridylolefins with CO and ethylene in the presence of a catalytic amount of Ru-3(CO)(12) in toluene results in propionylation at an olefinic C-H bond in pyridylolefins. The carbonylation occurs regioselectively ata position gamma to the pyridine nitrogen. Transition-metal complexes other than Ru3(CO)12 that have thus far been examined exhibit no catalytic activity, and ethylene serves as the only olefin. A similar tendency has been noted in the previously reported carbonylation at a C-H bond in the benzene ring of pyridylbenzenes. This reaction can be also applied to N-(2-pyridyl)enamines, in which an olefin unit is separated from the pyridine ring by an sp(3)-nitrogen atom. The reaction of N-(2-pyridyl)enamines with CO and ethylene gives the corresponding ethyl ketones as the coupling products. Interestingly, Rh-4(CO)(12) also shows high catalytic activity in the case of N-(2-pyridyl)enamines. In addition, olefins such as propene, 1-hexene, 3,3-dimethyl-1-butene, styrene, cyclopentene, acryl acid methyl ester, ethyl vinyl ether, and trimethylvinylsilane can also be used. This is in sharp contrast to the case of the carbonylation at a C-H bond in pyridylbenzenes reported previously and to the results of pyridylolefins as mentioned above, where Ru-3(CO)(12) is the only active catalyst and hexene-cannot substitute for ethylene.
• HANKOVSZKY V. H.; HIDEG K.; LLOYD D.; MCNAB H., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 5, 1345-1350
  作者：HANKOVSZKY V. H.、 HIDEG K.、 LLOYD D.、 MCNAB H.

  DOI：——

  日期：——