1-(间三氟甲基苯基)环己烯 | 60652-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(间三氟甲基苯基)环己烯
• 英文名称: 1-(m-trifluoromethylphenyl)cyclohexene
• 英文别名: 1-(trifluoromethyl )-3-(cyclohexen-1-yl)benzene；1-m-Trifluormethylphenylcyclohexen；1-(1-Cyclohexenyl)-3-(trifluoromethyl)benzene；1-(cyclohexen-1-yl)-3-(trifluoromethyl)benzene
• CAS: 60652-10-0
• 化学式: C₁₃H₁₃F₃
• 分子量: 226.241
• InChiKey: XRUMKQRWRNFAPG-UHFFFAOYSA-N

物化性质

• 沸点：
  261.4±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 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：
  3

反应信息

• 作为反应物：
  描述：

  1-(间三氟甲基苯基)环己烯 在 sulfur 作用下， 生成 3-(三氟甲基)联苯
  参考文献：
  名称：

  .sigma.-Sulfurane chemistry. Effect of substituents on the coupling reactions

  摘要：

  DOI：

  10.1021/ja00797a033
• 作为产物：
  描述：

  m-trifluoro-methyl-phenyl-magnesium bromide 在 硫酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 生成 1-(间三氟甲基苯基)环己烯
  参考文献：
  名称：

  Balsamo,A. et al., Gazzetta Chimica Italiana, 1976, vol. 106, p. 77 - 83

  摘要：

  DOI：

文献信息

• Achieving Vinylic Selectivity in Mizoroki-Heck Reaction of Cyclic Olefins
  作者：Xiaojin Wu、Yunpeng Lu、Hajime Hirao、Jianrong Steve Zhou

  DOI：10.1002/chem.201204427

  日期：2013.5.3

  In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium–hydride‐catalyzed isomerization of the initial products. Thus, a specific catalyst must be used

  在环烯烃的Heck反应中，产物通常具有芳基，该芳基最终在烯丙基和/或均烯丙基位置。我们在本文中报道了新的选择性，该选择性将芳基添加到乙烯基位置。各种环大小的环烯烃均能很好地发挥作用。所需的异构体是通过氢化钯催化的初始产物异构化反应制得的。因此，必须使用特定的催化剂，以使其可以在一组反应条件下进行两项工作。
• [EN] A PROCESS FOR THE PALLADIUM-CATALYZED COUPLING OF TERMINAL ALKYNES WITH ARYL TOSYLATES<br/>[FR] PROCÉDÉ POUR LE COUPLAGE CATALYSÉ PAR LE PALLADIUM D'ALCYNES TERMINALES AVEC DES TOSYLATES D'ARYLE
  申请人：SANOFI AVENTIS

  公开号：WO2009003589A1

  公开（公告）日：2009-01-08

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula (I) useful for the production of intermediates in the preparation for pharmaceuticals, diagnostic agents, liquid crystals, polymers, herbicides, fungicidals, nematicidals, parasiticides, insecticides, acaricides and arthropodicides.

  本发明涉及一种用于选择性合成公式(I)化合物的过程，其中R1；R2；R3；R4；R5；J和W具有声明中指示的含义。本发明提供了一种高效和通用的钯催化偶联过程，可将芳基磺酸酯与末端炔烃偶联，形成一系列取代的、多功能的芳基-1-炔烃，其化学式为(I)，用于制备制药品、诊断试剂、液晶、聚合物、除草剂、杀菌剂、线虫杀灭剂、寄生虫杀灭剂、杀虫剂、螨虫剂和节肢动物杀灭剂的中间体。
• 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。
• Chloropalladation of 1-aryl-ω-methylenebicyclo[n.1.0]alkanes
  作者：William A. Donaldson、Jeffrey T. North、James A. Gruetzmacher、Michael Finley、Daniel J. Stepuazek

  DOI：10.1016/s0040-4020(01)82007-x

  日期：1990.1

  The chloropalladation of 1-aryl-ω-methylenebicyclo[n.l.0]alkanes affords a mixture of (1-aryl-3-chloro-2-methylenecycloalkyl) - and (3-aryl-3-chloro-2-methylenecycloalkyl)palladium chloride dimers in excellent yield. These products have been characterized by 1H NMR spectroscopy. The regioselectivity of the chloropalladation appears to be dependent on ring strain, steric hinderance and to some extent

  1-芳基-ω-亚甲基双环[nl0]烷烃的氯化钯制得（1-芳基-3-氯-2-亚甲基环烷基）-和（3-芳基-3-氯-2-亚甲基环烷基）氯化钯二聚体的混合物。优良的产量。这些产物已经通过1 H NMR光谱表征。氯palpalation的区域选择性似乎取决于环应变，空间位阻，并在某种程度上取决于芳基取代基稳定部分正电荷的能力。
• Process for the palladium-catalyzed coupling of terminal alkynes with aryl tosylates
  申请人：RKYEK Omar

  公开号：US20100261910A1

  公开（公告）日：2010-10-14

  The present invention relates to a process for the regioselective synthesis of compounds of the formula (I), wherein R1; R2; R3; R4; R5; J and W have the meanings indicated in the claims. The present invention provides an efficient and general palladium-catalyzed coupling process for aryl tosylates with terminal alkynes to a wide variety of substituted, multifunctional aryl-1-alkynes of the formula I.

  本发明涉及一种合成式(I)化合物的区域选择性合成方法，其中R1、R2、R3、R4、R5、J和W的含义如权利要求所示。本发明提供了一种高效、通用的钯催化偶联方法，用于将芳基磺酸酯与末端炔烃耦合成式I的多取代多功能芳基-1-炔烃。