cyclohexyl(phenylethynyl)sulfane | 1612219-38-1

• 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: cyclohexyl(phenylethynyl)sulfane
• 英文别名: 2-Cyclohexylsulfanylethynylbenzene
• CAS: 1612219-38-1
• 化学式: C₁₄H₁₆S
• 分子量: 216.347
• InChiKey: GPTGXMMUZJTNEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cyclohexyl(phenylethynyl)sulfane 在 oxone||potassium monopersulfate triple salt 、 三氟化硼乙醚 、 NiCl₂(PPh₃)(IPr) 、 sodium sulfate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 0.17h， 生成 2-(cyclohexylthio)-5-methyl-3-phenyl-4-(4-(trifluoromethyl)phenyl)furan
  参考文献：
  名称：

  Tandem Cross-Coupling of Alkynyl Sulfides and Alkynyl Sulfoxides/[3,3]-Sulfonium Rearrangement to Construct Tetrasubstituted Furans

  摘要：

  DOI：

  10.1021/acs.orglett.1c04242
• 作为产物：
  描述：

  (±)-(E)-1-(cyclohexylthio)-N,N-diethyl-2-phenylethenesulfonamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 0.5h， 以71%的产率得到cyclohexyl(phenylethynyl)sulfane
  参考文献：
  名称：

  Transition-Metal-Free Synthesis of Ynol Ethers and Thioynol Ethers via Displacement at sp Centers: A Revised Mechanistic Pathway

  摘要：

  We present here valuable extensions to our previous work in preparing highly functionalized, heteroatom-substituted alkynes via displacement at an sp center. Our results show that a wide range of ynol ethers can be prepared by the same methodology and that the same protocol can be applied to the synthesis of synthetically useful thioynol ethers. We also present new observations that have led us to revise our original hypothesis in favor of a pathway involving radical intermediates.

  DOI：

  10.1021/jo500814y

文献信息

• An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation
  作者：Byron K. Peters、Taigang Zhou、Janjira Rujirawanich、Alban Cadu、Thishana Singh、Wangchuk Rabten、Sutthichat Kerdphon、Pher G. Andersson

  DOI：10.1021/ja5079877

  日期：2014.11.26

  sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation

  使用铱催化的不对称氢化反应制备了几种手性磺酰基化合物。研究了乙烯基、烯丙基和高烯丙基砜的取代，无论烯烃相对于砜的位置如何，都保持了高对映选择性。二烷基取代获得了令人印象深刻的立体选择性，这通常是氢化中具有挑战性的底物。正如预期的那样，体积更大的 Z 底物比相应的 E 异构体氢化得更慢，并且对映选择性略低。
• An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre
  作者：Roomi Mohima Chowdhury、Jonathan D. Wilden

  DOI：10.1039/c5ob00494b

  日期：——

  A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N′-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.

  一种简单高产率的芳基炔基硫醚的制备方法被提出。在胺介质（二甲胺或N,N'-二甲基乙二胺）存在下，氯代乙炔与硫醇盐反应可高产率地生成炔基硫醚。炔基氯化物可从母体炔烃轻松制备。
• Highly dispersed Ni₂P nanoparticles on N,P-codoped carbon for efficient cross-dehydrogenative coupling to access alkynyl thioethers
  作者：Tao Song、Peng Ren、Jianliang Xiao、Youzhu Yuan、Yong Yang

  DOI：10.1039/c9gc04137k

  日期：——

  A Ni₂P nanoparticle dispersed on N,P-codoped carbon material was developed for efficient synthesis of alkynyl thioethers via a cross-dehydrogenative coupling (CDC) strategy under base- and ligand-free conditions using air as the oxidant.

  一种分散在N,P-共掺杂碳材料上的Ni₂P纳米颗粒被开发出来，用于在无碱和配体的条件下利用空气作为氧化剂，通过交叉脱氢偶联（CDC）策略高效合成炔基硫醚。
• Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers
  作者：Davide Bello、David O'Hagan

  DOI：10.3762/bjoc.11.205

  日期：——

  A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et₃N, a process that requires Lewis acid activation using BF₃·Et₂O and TiF₄. The method gives access to a range of α-fluorovinyl thioethers, some in high stereoselectivity with the Z-isomer predominating over the E-isomer. The α-fluorovinyl thioether motif has prospects as a steric and electronic mimetic of thioester enols and enolates, important intermediates in enzymatic C–C bond forming reactions. The method opens access to appropriate analogues for investigations in this direction.

  报道了一种制备α-氟乙烯硫醚的新方法，涉及使用3HF·Et₃N对炔基硫醚进行氢氟化，该过程需要使用BF₃·Et₂O和TiF_{4>进行Lewis酸活化。该方法可以获得一系列α-氟乙烯硫醚，其中一些具有高立体选择性，其中Z-异构体优于E-异构体。α-氟乙烯硫醚结构具有作为硫酯烯醇和烯醇负离子的立体和电子模拟物的前景，这些是酶催化的C-C键形成反应中的重要中间体。该方法为在这个方向上进行研究提供了适当的类似物。}
• Synthesis of Thioalkynes by Desilylative Sonogashira Cross‐Coupling of Aryl Iodides and 1‐Methylthio‐2‐(trimethylsilyl)ethyne
  作者：Yang Cao、Yang Huang、Paul R. Blakemore

  DOI：10.1002/ejoc.202200498

  日期：2022.9.13

  An efficient and operationally straightforward synthesis of 1-methylthio-2-arylethyne derivatives is described based on a desilylative Sonogashira cross-coupling between aryl iodides and a silylated surrogate for methylthioacetylene (Me3SiCCSMe). Extension of the process to a selection of other thioether types is also documented.

  基于芳基碘化物和甲硫基乙炔 (Me 3 SiCCSMe)的甲硅烷基化替代物之间的脱甲硅烷基 Sonogashira 交叉偶联，描述了一种高效且操作简单的 1-甲硫基-2-芳基乙炔衍生物合成方法。还记录了将该过程扩展到选择其他硫醚类型。