1-(4-环戊-2-烯-1-基苯基)乙酮 | 115419-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-环戊-2-烯-1-基苯基)乙酮
• 英文名称: 1-(4-(cyclopent-2-en-1-yl)phenyl)ethan-1-one
• 英文别名: 1-[4-(Cyclopent-2-en-1-yl)phenyl]ethan-1-one；1-(4-cyclopent-2-en-1-ylphenyl)ethanone
• CAS: 115419-31-3
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: NPHHURYODSYUJX-UHFFFAOYSA-N

物化性质

• 沸点：
  305.9±31.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 、 环戊烯 在 palladium diacetate 四丁基氯化铵 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 108.0h， 以94%的产率得到1-(4-环戊-2-烯-1-基苯基)乙酮
  参考文献：
  名称：

  Palladium-catalyzed intermolecular allylic arylation of cyloalkenes

  摘要：

  DOI：

  10.1016/s0040-4039(00)82478-8

文献信息

• Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst
  作者：Florian Berthiol、Henri Doucet、Maurice Santelli

  DOI：10.1016/s0040-4039(02)02788-0

  日期：2003.2

  4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)]2 system catalyses efficiently the Heck reaction of aryl halides with linear alkenes such as pent-1-ene, oct-1-ene or dec-1-ene. Selectivities up to 70% in favour of E-1-arylalk-1-ene isomers can be obtained. In the presence of cyclic alkenes the selectivities of the reactions strongly depends on the ring size. Addition to cyclohexene or cycloheptene led mainly

  cis，cis，cis -1,2,3,4-Tetrakis（diphenylphosphinomethyl）cyclopentane / [PdCl（C 3 H 5）] 2体系有效地催化芳基卤化物与线性烯烃（如戊-1-烯）的Heck反应，辛-1-烯或癸-1-烯。选择性高达赞成70％Ë -1- arylalk -1-烯异构体可制得。在环状烯烃的存在下，反应的选择性很大程度上取决于环的大小。除环己烯或环庚烯外，主要产生1-芳基环烷-3-烯衍生物。另一方面，除环辛烯外，还生成了1-芳基环烷-1-烯加合物。
• Highly Selective Palladium-Catalyzed Heck Reactions of Aryl Bromides with Cycloalkenes
  作者：Christian G. Hartung、Klaus Köhler、Matthias Beller

  DOI：10.1021/ol9901063

  日期：1999.9.1

  [reaction: see text] The influence of palladium catalysts and reaction conditions on the selectivity of Heck reactions of aryl bromides with cyclohexene and cyclopentene has been investigated. It is shown that the addition of DMSO as a cosolvent leads to improved selectivities of nonconjugated aryl olefins. On the other hand, high selectivities for conjugated arylcyclopentenes have been obtained with

  [反应：见正文]研究了钯催化剂和反应条件对芳基溴化物与环己烯和环戊烯的Heck反应选择性的影响。结果表明，添加DMSO作为助溶剂可提高非共轭芳基烯烃的选择性。另一方面，通过催化体系DMA / Na2CO3 / Pd2（dba）3 x dba / PCy3获得了对共轭芳基环戊烯的高选择性。
• Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands
  作者：Matthew G. Lauer、Mallory K. Thompson、Kevin H. Shaughnessy

  DOI：10.1021/jo501840u

  日期：2014.11.21

  The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
• Palladium-catalyzed intermolecular allylic arylation of cyloalkenes
  作者：Richard C. Larock、Bruce E. Baker

  DOI：10.1016/s0040-4039(00)82478-8

  日期：1988.1