3’-(trifluoromethyl)-1,2,3,4-tetrahydro-1,1'-biphenyl

• 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’-(trifluoromethyl)-1,2,3,4-tetrahydro-1,1'-biphenyl
• 英文别名: 3'-(trifluoromethyl)-1,2,3,4-tetrahydro-1,1'-biphenyl；3-[3-(trifluoromethyl)phenyl]cyclohexene；1-(2-Cyclohexenyl)-3-(trifluoromethyl)benzene；1-cyclohex-2-en-1-yl-3-(trifluoromethyl)benzene
• 化学式: C₁₃H₁₃F₃
• 分子量: 226.241
• InChiKey: DTLAABBGSVRJCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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

• 作为产物：
  描述：

  2-环己烯醇 在 吡啶 、 indium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 3’-(trifluoromethyl)-1,2,3,4-tetrahydro-1,1'-biphenyl
  参考文献：
  名称：

  Efficient Palladium-Catalyzed Nucleophilic Addition of Triorganoindium Reagents to Carbocyclic Derivatives

  摘要：

  Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1-3 mol % Pd-2(dba)(3) to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.

  DOI：

  10.1021/jo0357162

文献信息

• Preparation of Solid, Substituted Allylic Zinc Reagents and Their Reactions with Electrophiles
  作者：Mario Ellwart、Paul Knochel

  DOI：10.1002/anie.201504354

  日期：2015.9.1

  The treatment of various allylic chlorides or bromides with zinc dust in the presence of lithium chloride and magnesium pivalate (Mg(OCOtBu)2) in THF affords allylic zinc reagents which, after evaporation of the solvent, produce solid zinc reagents that display excellent thermal stability. These allylic reagents undergo Pd‐catalyzed cross‐coupling reactions with PEPPSI‐IPent, as well as highly regioselective

  在氯化锂和新戊酸镁（Mg（OCO t Bu）2）在THF中存在的情况下，用锌粉处理各种烯丙基氯化物或溴化物，可得到烯丙基锌试剂，该溶剂蒸发后，生成的固态锌试剂显示出优异的热稳定性。这些烯丙基试剂与PEPPSI-IPent进行Pd催化的交叉偶联反应，以及对芳基酮和醛进行高度区域选择性和非对映选择性的加成。酰化与各种酰氯区域选择性地产生相应的高烯丙基酮，用新的C  C键总是被形成在烯丙基系统的最受阻碳。
• [EN] ORGANOZINC REAGENTS AND PROCESSES FOR PREPARING AND USING THE SAME<br/>[FR] RÉACTIFS ORGANOZINCIQUES ET LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：UNIV MUENCHEN LUDWIG MAXIMILIANS

  公开号：WO2016146689A1

  公开（公告）日：2016-09-22

  Provided is an organozinc composition comprising (a) an organozinc complex carrying an allylic ligand, (b) a magnesium component and (c) a lithium component. The organozinc composition is useful as a synthetic intermediate with excellent reactivity and selectivity, and can be stored for extended periods of time without loss of activity. Moreover, a process for the preparation of the organozinc composition and synthetic procedures making use of the organozinc composition are provided.

  提供了一种有机锌组合物，其包含（a）携带烯丙基配体的烷基锌络合物，（b）镁组分和（c）锂组分。该有机锌组合物作为具有优异反应性和选择性的合成中间体非常有用，并且可以长期储存而不会失去活性。此外，还提供了制备该有机锌组合物的方法以及利用该有机锌组合物的合成程序。
• 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。
• 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。
• Organozinc reagents and processes for preparing and using the same
  申请人：Ludwig-Maximilians-Universität München

  公开号：EP3070083A1

  公开（公告）日：2016-09-21

  Provided is an organozinc composition comprising (a) an organozinc complex carrying an allylic ligand, (b) a magnesium component and (c) a lithium component. The organozinc composition is useful as a synthetic intermediate with excellent reactivity and selectivity, and can be stored for extended periods of time without loss of activity. Moreover, a process for the preparation of the organozinc composition and synthetic procedures making use of the organozinc composition are provided.

  本发明提供了一种有机锌组合物，该组合物包含 (a) 带有烯丙基配体的有机锌络合物，(b) 镁组分和 (c) 锂组分。该有机锌组合物可用作合成中间体，具有极佳的反应性和选择性，可长期保存而不会失去活性。此外，还提供了制备该有机锌组合物的工艺和利用该有机锌组合物的合成程序。