[(1Z)-4-phenyl-1-(phenylsulfanyl)but-1-en-3-ynyl]benzene | 142144-51-2

• 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: [(1Z)-4-phenyl-1-(phenylsulfanyl)but-1-en-3-ynyl]benzene
• 英文别名: (Z)-1,4-diphenyl-1-(phenylthio)-1-buten-3-yne；(Z)-1,4-diphenyl-2-(phenylthio)but-1-en-3-yne；(Z)-1,4-Diphenyl-1-phenylthio-but-1-en-3-in；(Z)-1-phenylthio-1,4-diphenylbut-1-en-3-yne；[(Z)-1,4-diphenylbut-1-en-3-ynyl]sulfanylbenzene
• CAS: 142144-51-2
• 化学式: C₂₂H₁₆S
• 分子量: 312.435
• InChiKey: QYERVDVAYWJRJK-PYCFMQQDSA-N

物化性质

• 沸点：
  462.4±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  diphenyl(phenylethynyl)selenonium triflate 在 苯胺 正丁基锂 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 6.0h， 生成 [(1Z)-4-phenyl-1-(phenylsulfanyl)but-1-en-3-ynyl]benzene
  参考文献：
  名称：

  使用β-烷基硫代烯基硒鎓盐的新型立体选择性制备各种乙烯基硫化物衍生物的方法

  摘要：

  用催化量的三乙胺处理炔基硒鎓盐和各种硫酚衍生物，以良好的收率得到β-芳基硫基烯基硒鎓盐。如此制备的烯基硒鎓盐与亲核试剂如乙炔化物，硫醇盐和醇盐反应，以高收率生产（Z）-β-芳硫基-α-官能化的乙烯。在β侧链上带有羟基的乙烯基硒鎓盐在用氢化钠处理后产生分子内环化反应，从而生成含有硫和氧原子的中元杂环化合物。给出（Z）-β-芳硫基-α-官能化的乙烯的反应将通过形成亚硒酸酯中间体进行，然后进行配体偶联反应。

  DOI：

  10.1021/jo000640k

文献信息

• Palladium-Catalyzed Alkynylthiolation of Alkynes with Triisopropylsilylethynyl Sulfide
  作者：Masayuki Iwasaki、Daishi Fujino、Tatsuya Wada、Azusa Kondoh、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1002/asia.201100643

  日期：2011.12.2

  Regio‐ and stereoselective addition of a silyl‐substituted alkynyl sulfide to various terminal alkynes proceeds in the presence of a palladium catalyst to give (Z)‐1‐thio‐1,3‐enynes, which are useful building blocks for the synthesis of polysubstituted 1,3‐enynes. Addition to internal alkynes also takes place under solvent‐free conditions (see scheme).

  在钯催化剂的存在下，将甲硅烷基取代的炔基硫醚在区域和立体选择性地加成到各种末端炔烃上，得到（Z）-1-硫-1,3-烯炔，这对于合成多取代基是有用的结构单元1,3-烯炔 在没有溶剂的条件下，内部炔烃也要加成（见方案）。
• Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives
  作者：Srinivasan Chandrasekaran、Cheerladinne Venkateswarlu

  DOI：10.1055/s-0034-1379330

  日期：——

  Abstract This work describes an efficient and stereoselective method for the hydrothiolation and -selenation of buta-1,3-diyne derivatives using diaryl disulfides or diselenides, respectively. In the presence of rongalite (HOCH2SO2Na) and potassium carbonate, buta-1,3-diynes undergo stereoselective addition of the thiolate or selenide anion generated in situ from diaryl disulfides or diselenides to

  摘要 这项工作描述了一种高效且立体选择性的方法，分别使用二芳基二硫化物或二硒化物对buta-1,3-diyne衍生物进行氢硫醇化和-硒化。在有钙锌矿（HOCH 2 SO 2 Na）和碳酸钾的情况下，对buta-1,3-diynes进行立体选择加成反应，该反应由二芳基二硫化物或二硒化物原位产生的硫醇盐或硒化物阴离子提供相应的（Z）-1-分别是亚硫烷基或（Z）-1-硒基烷基-1-en-3-炔衍生物。Buta-1,3-diynes与二芳基二硫化物或二硒化物在较高温度（70°C）下的反应以中等至良好的收率得到了单硫代/硒化和双硫代/硒化产物的混合物。 这项工作描述了一种高效且立体选择性的方法，分别使用二芳基二硫化物或二硒化物对buta-1,3-diyne衍生物进行氢硫醇化和-硒化。在有钙锌矿（HOCH 2 SO 2 Na）和碳酸钾的情况下，对buta-1,3-diynes进行立体选择加成反应，该反
• Synthesis of (Z)-1-Organylthiobut-1-en-3-ynes: Hydrothiolation of Symmetrical and Unsymmetrical Buta-1,3-diynes
  作者：Miguel Dabdoub、Adriano Baroni、Vânia Dabdoub、Eder Lenardão、Gabriela Hurtado、Sandro Barbosa、Palimécio Guerrero、Carlos Nazário、Luiz Viana、Amanda Santana

  DOI：10.1055/s-0028-1088196

  日期：2009.4

  Hydrothiolation of 1-organylbuta-1,3-diynes and 1,4-diorganylbuta-1,3-diynes with the sodium organylthiolate anions, which were generated in situ by reacting diphenyl and dibutyl di­sulfide with NaBH4 in ethanol, results in the regio-, stereo-, and chemoselective formation of (Z)-1-organylthio-4-organylbut-1-en-3-ynes and (Z)-1-organylthio-1,4-diorganylbut-1-en-3-ynes, respectively.

  1-organylbuta-1,3-diynes 和 1,4-diorganylbuta-1,3-diynes 与organylthiolate 钠阴离子发生氢硫化反应、分别生成了 (Z)-1-organylthio-4-organylbut-1-en-3-ynes 和 (Z)-1-organylthio-1,4-diorganylbut-1-en-3-ynes。
• Synthesis of (Z)-organylthioenynes using KF/Al2O3/solvent as recyclable system
  作者：Diego Alves、Maraisa Sachini、Raquel G. Jacob、Eder J. Lenardão、Maria E. Contreira、Lucielli Savegnago、Gelson Perin

  DOI：10.1016/j.tetlet.2010.11.009

  日期：2011.1

  PEG-400 and glycerol were successfully used as recyclable solvents for the synthesis of several organylthioenynes in good to excellent yields and high selectivity using solid supported catalyst (KF/Al2O3). This easy, general and improved method furnishes the corresponding alkenyl sulfides preferentially with Z configuration. The catalytic system and the glycerol or PEG-400 can be reused up to three times without previous treatment with comparable activity. (C) 2010 Elsevier Ltd. All rights reserved.
• Selective Synthesis of (<i>Z</i>)-Chalcogenoenynes and (<i>Z</i>,<i>Z</i>)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400
  作者：Renata G. Lara、Liane K. Soares、Raquel G. Jacob、Ricardo F. Schumacher、Gelson Perin

  DOI：10.5935/0103-5053.20160094

  日期：——

  We present here our results on the temperature controlled, selective hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes with nucleophilic species of selenium, tellurium and sulfur generated in situ from the respective diaryl dichalcogenide and NaBH4. Using polyethylene glycol (PEG)-400 at 30 degrees C the (Z)-chalcogenoenynes are obtained and at 90 degrees C the (Z, Z)-bis-chalcogen-1,3-butadienes are produced in good to excellent yields. Alternatively to conventional oil bath heating, the use of microwave irradiation is also presented as an alternative energy source that provides the expected products in few minutes.