(E)-(4-phenylbut-1-en-1-yl)(trifluoromethyl)sulfane

• 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: (E)-(4-phenylbut-1-en-1-yl)(trifluoromethyl)sulfane
• 英文别名: (4-phenylbut-1-en-1-yl)(trifluoromethyl)sulfane；[(E)-4-(trifluoromethylsulfanyl)but-3-enyl]benzene
• 化学式: C₁₁H₁₁F₃S
• 分子量: 232.27
• InChiKey: MHZIDISDNMTTBW-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(4-phenylbut-1-en-1-yl)(trifluoromethyl)sulfane 在 1,2-bis{di(4-methoxyphenyl)phosphino}benzene 、 copper diacetate 、 频那醇硼烷 作用下， 以 四氢呋喃 为溶剂， 以11%的产率得到(4-phenylbutyl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  Asymmetric Synthesis of SCF3‐Substituted Alkylboronates by Copper‐Catalyzed Hydroboration of 1‐Trifluoromethylthioalkenes

  摘要：

  A synthetic method for preparation of optically active trifluoromethylthio (SCF3) compounds by a copper‐catalyzed regio‐ and enantioselective hydroboration of 1‐trifluoromethylthioalkenes with H–Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF3‐contaning alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF3 molecules. Computational studies suggest that the SCF3 group successfully controls the regioselectivity in the reaction.

  DOI：

  10.1002/anie.202403337
• 作为产物：
  描述：

  (三氟甲硫基)银(I) 、 (E)-1-碘-4-苯基-1-丁烯 在 吡啶 、 copper(l) iodide 作用下， 以88 %的产率得到(E)-(4-phenylbut-1-en-1-yl)(trifluoromethyl)sulfane
  参考文献：
  名称：

  Copper-mediated Trifluoromethylthiolation of Alkenyl Iodides with AgSCF3

  摘要：

  摘要 利用 AgSCF3 开发了铜介导的烯基碘化物三氟甲基硫代反应。由铜盐和 AgSCF3 原位生成的 CuSCF3 物种可与烯基碘化物偶联，高效生成相应的三氟甲基硫代烯。反应条件与各种官能团兼容。此外，它还可以进行放大合成，甚至在克级规模上提供所需的三氟甲基硫代产物。

  DOI：

  10.1246/cl.230335

文献信息

• Hydrotrifluoromethylthiolation of Unactivated Alkenes and Alkynes with Trifluoromethanesulfonic Anhydride through Deoxygenative Reduction and Photoredox Radical Processes
  作者：Yao Ouyang、Xiu‐Hua Xu、Feng‐Ling Qing

  DOI：10.1002/anie.201911323

  日期：2019.12.16

  trifluoromethanesulfonic anhydride (Tf2 O) as a radical trifluoromethylthiolating reagent. Hydrotrifluoromethylthiolation of unactivated alkenes and alkynes with Tf2 O in the presence of PMePh2 and H2 O under visible-light photoredox catalysis gave the addition products. The trifluoromethylthio radical (. SCF3 ) was first formed from Tf2 O through a photoredox radical processes and deoxygenative reduction of

  三氟甲硫基化反应中的一个持续挑战是使用较便宜且容易获得的三氟甲硫基来源。在此，我们公开了空前的三氟甲磺酸酐（Tf2O）作为自由基三氟甲基硫醇化试剂的用途。在可见光光氧化还原催化下，在PMePh2和H2 O存在下，用Tf2 O对未活化的烯烃和炔烃进行加氢三氟甲基硫醇化反应，得到加成产物。首先通过光氧化还原自由基过程和PMePh2的脱氧还原反应，由Tf2 O形成三氟甲硫基（。SCF3），H2 O用作氢三氟甲硫基化反应的H原子供体。该反应提供了自由基三氟甲基硫醇化的新策略。
• Facile synthesis of α-trifluoromethylthio phosphonium ylides with a constrained trifluoromethylthiooxide <i>via</i> a proton-transfer procedure
  作者：Chengyao Kimmy Cao、Yue Zhang、Tianlei Lan、Wei Liu、Chao Chen

  DOI：10.1039/c9cc04234b

  日期：——

  Synthesis of α-trifluoromethylthio(CF3S–)phosphonium ylides is easily accomplished with a constrained trifluoromethylthiooxide via a proton-transfer procedure without extra base. These CF3S-substituted phosphonium ylides could be applied to Wittig reactions to provide functionalised alkenes in one-pot with high yields.

  用受限的三氟甲硫醇通过质子转移程序，无需额外的碱，即可轻松完成α-三氟甲硫基（CF 3 S–）phosph的合成。这些CF 3 S-取代的磷鎓烷基化物可用于Wittig反应，以高产率在一锅中提供官能化的烯烃。
• Copper-Catalyzed Trifluoromethyl Thiolation-Mild and Efficient Synthesis of Trifluoromethyl Thioethers
  作者：Magnus Rueping、Nikita Tolstoluzhsky、Pavlo Nikolaienko

  DOI：10.1002/chem.201302692

  日期：2013.10.11

  Mild‐mannered sulfur: A general method for the synthesis of vinyl trifluoromethyl thioethers starting from readily available di‐, tri‐, and tetrasubstituted vinyl iodides was developed (see scheme). A wide variety of substrates were applied in the reaction with CuSCF3 to give the corresponding products in high yields, within short reaction times, with retention of the initial E/Z isomer ratio. In addition

  轻度硫：开发了一种从容易获得的二，三和四取代乙烯基碘开始合成乙烯基三氟甲基硫醚的通用方法（请参见方案）。在与CuSCF 3的反应中使用了多种底物，从而在较短的反应时间内以高收率得到了相应的产物，并保留了初始的E / Z异构体比。此外，还开发了铜催化的三氟甲基硫醚协议。
• Copper-mediated Trifluoromethylthiolation of Alkenyl Iodides with AgSCF3
  作者：Yuki Kojima、Koji Hirano

  DOI：10.1246/cl.230335

  日期：2023.10.5

  A copper-mediated trifluoromethylthiolation of alkenyl iodides with AgSCF3 has been developed. CuSCF3 species generated in-situ from a copper salt and AgSCF3 can be coupled with alkenyl iodides to produce the corresponding trifluoromethylthioalkenes efficiently. The reaction conditions are compatible with various functional groups. Moreover, its scale-up synthesis is also possible to provide the desired trifluoromethylthiolated product even on a gram-scale.

  摘要 利用 AgSCF3 开发了铜介导的烯基碘化物三氟甲基硫代反应。由铜盐和 AgSCF3 原位生成的 CuSCF3 物种可与烯基碘化物偶联，高效生成相应的三氟甲基硫代烯。反应条件与各种官能团兼容。此外，它还可以进行放大合成，甚至在克级规模上提供所需的三氟甲基硫代产物。
• Asymmetric Synthesis of SCF3‐Substituted Alkylboronates by Copper‐Catalyzed Hydroboration of 1‐Trifluoromethylthioalkenes
  作者：Yuki Kojima、Yuji Nishii、Koji Hirano

  DOI：10.1002/anie.202403337

  日期：——

  A synthetic method for preparation of optically active trifluoromethylthio (SCF3) compounds by a copper‐catalyzed regio‐ and enantioselective hydroboration of 1‐trifluoromethylthioalkenes with H–Bpin has been developed. The enantioselective hydrocupration of an in situ generated CuH species and subsequent boration reaction generate a chiral SCF3‐contaning alkylboronate, of which Bpin moiety can be further transformed to deliver various optically active SCF3 molecules. Computational studies suggest that the SCF3 group successfully controls the regioselectivity in the reaction.