3-phenylcycloheptene | 19217-54-0

• 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: 3-phenylcycloheptene
• 英文别名: 3-Phenylcyclohepten-(1)；3-Phenyl-cyclohepten；3-Phenylcyclohepten；3-Phenyl-1-cycloheptene
• CAS: 19217-54-0
• 化学式: C₁₃H₁₆
• 分子量: 172.27
• InChiKey: ZFBUBYLVRDQACY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-phenylcycloheptene 以 苯 为溶剂， 生成 2-phenylmethylenecyclohexane 、 2-phenylbicyclo<4.1.0>heptane 、 2-Phenyl-norcaran
  参考文献：
  名称：

  Photochemical transformations. XIII. Photorearrangements of 3-phenylcycloheptene and some phenylnorcaranes

  摘要：

  DOI：

  10.1021/ja00853a035
• 作为产物：
  描述：

  3-phenylcycloheptanone 在 吡啶 、 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 生成 3-phenylcycloheptene
  参考文献：
  名称：

  Proximity effects. XLVIII. Aprotic decomposition of 2-phenylcyclooctanone p-toluenesulfonylhydrazone and 3-phenylcyclooctanone p-toluenesulfonylhydrazone

  摘要：

  DOI：

  10.1021/ja01002a020

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。
• Iron-Catalyzed Allylic Arylation of Olefins via C(sp³)–H Activation under Mild Conditions
  作者：Masaki Sekine、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ol400056z

  日期：2013.2.1

  cycloalkene or an allylbenzene derivative into a C–C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 °C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C–H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.

  芳基碘化物存在下的芳基格氏试剂可在催化量的Fe（acac）3和二膦配体在0°存在的情况下将环烯烃或烯丙基苯衍生物的烯丙基C–H键转换为C–C键C。反应的立体选择性和区域选择性，以及氘标记实验表明，CH键的活化是烯丙基铁中间体形成之前催化循环的缓慢步骤。
• Arylation of Olefins by Arylazo Aryl Sulfones under Palladium(0) Catalysis
  作者：Nobumasa Kamigata、Akira Satoh、Tetsuya Kondoh、Masayuki Kameyama

  DOI：10.1246/bcsj.61.3575

  日期：1988.10

  The palladium(0)-catalyzed reaction of arylazo aryl sulfones with olefins in benzene at 80°C gave aryl-substituted olefins in good yield. Diarylpalladium(II) species was proposed as an intermediate in this reaction.

  在 80°C 下，芳基偶氮芳基砜与烯烃在苯中的钯 (0) 催化反应以良好的收率得到芳基取代的烯烃。二芳基钯 (II) 物种被提议作为该反应的中间体。
• Copper-Catalyzed γ-Selective and Stereospecific Allyl−Aryl Coupling between (<i>Z</i>)-Acyclic and Cyclic Allylic Phosphates and Arylboronates
  作者：Hirohisa Ohmiya、Natsumi Yokokawa、Masaya Sawamura

  DOI：10.1021/ol100841y

  日期：2010.5.21

  A Cu-catalyzed allyl−aryl coupling reaction between (Z)-acyclic or cyclic allylic phosphates and arylboronates proceeds with excellent γ-E-selectivity and 1,3-anti chirality transfer, which gives the corresponding coupling products with benzylic and allylic stereogenic centers. The wide availability and easy-to-handle nature of arylboronates, the inexpensiveness of the Cu catalyst system, and the high

  （Z）-无环或环状烯丙基磷酸酯与芳基硼酸酯之间的Cu催化的烯丙基-芳基偶联反应具有出色的γ-E-选择性和1,3-抗手性转移，从而产生了具有苄基和烯丙基立体异构中心的相应偶联产物。芳基硼酸酯的广泛可用性和易于处理的性质，Cu催化剂体系的廉价以及高区域选择性和立体选择性是该方案的吸引人的特征。
• Reaction of benzyne with cycloheptatriene preparation and thermolysis of some benzo(C9H10) hydrocarbons
  作者：L. Lombardo、D. Wege

  DOI：10.1016/s0040-4020(01)97089-9

  日期：1974.1

  The title reaction gave a 2+2 cycloadduct, 8,9-benzo-cis-bicyclo[5.2.0]nona-2,4,8-triene 7, together with ene product, 7-phenylcycloheptatriene. The structure of 7 was confirmed by catalytic reduction to give 8,9-benzo-cis-bicyclo[5.2.0]non-8-ene, which was also obtained in the reaction of benzyne with cycloheptene, and by reduction of the known 8,9-benzobicyclo[5.2.0]nona-1,8-diene. Other benzo(C9H10)

  标题反应得到2 + 2环加合物，8，9-苯并顺式-双环[5.2.0]壬娜-2，4，8-三烯7，以及烯产物7-苯基环庚三烯。的结构7通过催化还原证实，得到8,9-苯并顺-二环[5.2.0]壬-8-烯，其还与环庚苯炔的反应获得，并通过还原已知8的，9-苯并双环[5.2.0] nona-1,8-二烯。其它苯并（C 9 ħ 10已被合成的）烃是7,8- benzobicyclo [4.2.1]壬-2,4,7-三烯5，2,3- benzobicyclo [6.1.0]壬-2,4- ，6-三烯28和4,5-苯并双环[6.1.0] nona-2,4,6-三烯29。的热分解描述了7,28,29和3,4-苯并-外-内-四环[4.3.1.0 3,4 .0 7,9 ] dec-3-en-10-one，25的描述。