3-[2-(trifluoromethyl)phenyl]cyclohexene

• 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-[2-(trifluoromethyl)phenyl]cyclohexene
• 英文别名: 2'-(trifluoromethyl)-1,2,3,4-tetrahydro-1,1'-biphenyl；2-(9,9-difluoro-2,3,4,4a,9,9a-hexahydro-1H-fluoren-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；1-Cyclohex-2-en-1-yl-2-(trifluoromethyl)benzene
• 化学式: C₁₃H₁₃F₃
• 分子量: 226.241
• InChiKey: MMOBJGNDKZJUKZ-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

• 作为反应物：
  描述：

  联硼酸频那醇酯 、 3-[2-(trifluoromethyl)phenyl]cyclohexene 在 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine 、 copper(l) cyanide 、 sodium iodide 、 potassium hydroxide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以76 %的产率得到2-(9,9-difluoro-2,3,4,4a,9,9a-hexahydro-1H-fluoren-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  光氧化还原和铜双重催化实现烯烃的脱氟烷基硼化

  摘要：

  本文报道了通过双光氧化还原/铜催化，烯烃与三氟甲基和双(频哪醇)二硼的基于自由基的三组分脱氟烷基硼化反应。该方案以高效率和反向区域选择性有效地获得具有合成价值的γ-宝石-二氟烷基硼酸酯。

  DOI：

  10.1002/anie.202315974
• 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-[2-(trifluoromethyl)phenyl]cyclohexene
  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 Polyfunctional Arylzinc Organometallics in Toluene by Halogen/Zinc Exchange Reactions
  作者：Moritz Balkenhohl、Dorothée S. Ziegler、Alexandre Desaintjean、Leonie J. Bole、Alan R. Kennedy、Eva Hevia、Paul Knochel

  DOI：10.1002/anie.201906898

  日期：2019.9.9

  toluene within 10 min to 5 h through an I/Zn or Br/Zn exchange reaction using bimetallic reagents of the general formula R'2 Zn⋅2 LiOR (R'=sBu, tBu, pTol). Highly sensitive functional groups, such as a triazine, a ketone, an aldehyde, or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of a plethora of functionalized (hetero)arenes after quenching with various electrophiles

  使用通式R'2Zn⋅2LiOR（R'= sBu）的双金属试剂，通过I / Zn或Br / Zn交换反应，在10分钟至5小时内，在甲苯中制备了多种多官能的二芳基和二杂芳基锌物质。 ，tBu，pTol）。在这些交换反应中可以耐受高度敏感的官能团，例如三嗪，酮，醛或硝基，从而可以在用各种亲电试剂淬灭后合成大量官能化的（杂）芳烃。对这些双金属混合物的组成和反应性的深入了解揭示了[R'2 Zn（OR）2 Li2]型高活性二有机二烷氧基锌酸锂的形成。
• Efficient Palladium-Catalyzed Nucleophilic Addition of Triorganoindium Reagents to Carbocyclic Derivatives
  作者：Lucas Baker、Thomas Minehan

  DOI：10.1021/jo0357162

  日期：2004.5.1

  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.
• Defluorinative Alkylboration of Alkenes Enabled by Dual Photoredox and Copper Catalysis
  作者：Yanmin Fan、Zhonghou Huang、Yi Lu、Shengqing Zhu、Lingling Chu

  DOI：10.1002/anie.202315974

  日期：2024.1.25

  three-component defluorinative alkylboration of alkenes with trifluoromethyls and bis(pinacolato)diboron via dual photoredox/copper catalysis. This protocol offers efficient access to synthetically valuable γ-gem-difluoroalkyl boronates with high efficiency and reversed regioselectivity.

  本文报道了通过双光氧化还原/铜催化，烯烃与三氟甲基和双(频哪醇)二硼的基于自由基的三组分脱氟烷基硼化反应。该方案以高效率和反向区域选择性有效地获得具有合成价值的γ-宝石-二氟烷基硼酸酯。