5-chloro-7,7,7-trifluoroheptyl benzoate | 1422056-68-5

• 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: 5-chloro-7,7,7-trifluoroheptyl benzoate
• 英文别名: (5-Chloro-7,7,7-trifluoroheptyl) benzoate
• CAS: 1422056-68-5
• 化学式: C₁₄H₁₆ClF₃O₂
• 分子量: 308.728
• InChiKey: MLZTYUYUCKDFNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲烷磺酰氯 、 Ru(2,2'-bipyridine)₃Cl₂·6H₂O 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 5-chloro-7,7,7-trifluoroheptyl benzoate
  参考文献：
  名称：

  未活化烯烃的催化氢三氟甲基化

  摘要：

  公开了使用 Umemoto 试剂作为 CF(3) 源和 MeOH 作为还原剂的未活化烯烃的可见光介导的氢三氟甲基化。这种有效的转变在室温下在 5 mol % Ru(bpy)(3)Cl(2) 存在下进行；该过程的特点是其操作简单和官能团耐受性。

  DOI：

  10.1021/ja401022x

文献信息

• Mn(OAc)₃-Mediated Addition Reactions of NaSO₂CF₃ and Perhalogenated Carboxylic Acids with Unactivated Alkenes Conjectured by a Single Electron Transfer and Halogen Abstraction Mechanism
  作者：Hui Sun、Guannan Cui、Huijian Shang、Bin Cui

  DOI：10.1021/acs.joc.0c02086

  日期：2020.12.4

  Mn(OAc)3·2H2O, CF3SO2Na, and perhalogenated carboxylic acids has been achieved. Perhalogenated carboxylic acids act as a halogen source and CF3SO2Na acts as a CF3 source. The reaction displayed good tolerance of functional groups in the substrates under mild conditions. The radical clock experiment and TEMPO inhibition experiment support a radical process. The halogen reagent competition experiment shows that the

  通过使用Mn（OAc）3 ·2H 2 O，CF 3 SO 2 Na和全卤代羧酸，可以实现烯烃的自由基卤代三氟甲基化。全卤代羧酸充当卤素源，CF 3 SO 2 Na充当CF 3源。该反应在温和条件下对底物中的官能团表现出良好的耐受性。自由基时钟实验和TEMPO抑制实验支持自由基过程。卤素试剂竞争实验表明，卤化过程的最后一步主要是通过卤素提取机理。
• Copper-Mediated Halotrifluoromethylation of Unactivated Alkenes
  作者：Won An、Neul Ha、Hyun Myung Lee、Yashwardhan R. Malpani、Duck-Hyung Lee、Young-Sik Jung、Soo Bong Han

  DOI：10.1002/adsc.201500731

  日期：2015.12.14

  A copper-mediated halotrifluoromethylation of unactivated alkenes using Umemoto’s reagent and copper(I) halide (CuX, X=Cl, Br, and I) was developed. The CuX species (CuI, CuBr, and CuCl) were chosen as the source for both copper and halides because of their benchtop stability, commercial availability, and relatively low cost. Simple exchange of the copper salt provided the desired simultaneous and

  开发了使用梅梅特试剂和卤化铜（I）（CuX，X = Cl，Br和I）的未激活的烯烃的铜介导的卤代三氟甲基化。选择CuX物种（CuI，CuBr和CuCl）作为铜和卤化物的来源，因为它们具有台式稳定性，商业可用性以及相对较低的成本。铜盐的简单交换提供了卤原子和CF 3基团同时和区域选择性地结合到各种烯烃上的期望效果。该方案为各种β-卤代三氟甲基化烷烃提供了一种有效而实用的途径。将CBr键进一步修饰为CB，CN和CS键。这些衍生化显示了后期修改的可行性。
• Trifluoromethylations of Alkenes Using PhICF₃Cl as Bifunctional Reagent
  作者：Cong Xu、Wanqiao Huang、Ruzhong Zhang、Chi Gao、Yuxin Li、Mang Wang

  DOI：10.1021/acs.joc.9b01901

  日期：2019.11.1

  of alkenes using PhICF3Cl as bifunctional reagent. Chlorotrifluoromethylated products were obtained when nonconjugated alkenes were treated with PhICF3Cl in 1,4-dioxane at 60 °C, while vinyl C-H trifluoromethylated products were obtained by further elimination of hydrochloride in the case of those conjugated alkene substrates in DMF. Broad substrate scope, especially including complex alkenes bearing

  我们描述了使用PhICF3Cl作为双功能试剂对烯烃进行三氟甲基化。当非共轭烯烃在60°C下于1,4-二恶烷中用PhICF3Cl处理时，得到氯三氟甲基化产物，而对于那些在DMF中共轭烯烃的底物，则通过进一步去除盐酸盐得到乙烯基CH三氟甲基化产物。广泛的底物范围，尤其是包括带有生物活性基序的复杂烯烃在内，表明这种温和的反应对于药物发现中的后期修饰是可行的。
• Vicinal Difunctionalization of Alkenes: Chlorotrifluoromethylation with CF₃SO₂Cl by Photoredox Catalysis
  作者：Se Hwan Oh、Yashwardhan R. Malpani、Neul Ha、Young-Sik Jung、Soo Bong Han

  DOI：10.1021/ol403716t

  日期：2014.3.7

  Photoredox-catalyzed vicinal chlorotrifluoromethylation of alkene is described. In the presence of Ru(Phen)(3)Cl-2, CF3SO2Cl was used as a source for the CF3 radical and chloride ion under visible light irradiation. Various terminal and internal alkenes were transformed to their vicinal chlorotrifluoromethylated derivatives. Biologically active compounds were applied under the condition to obtain desired products, suggesting that the method could be feasible for late-stage modification in drug discovery.