(Z)-1,2-bis(phenylthio)-3-hydroxy-1-propene | 137540-63-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-1,2-bis(phenylthio)-3-hydroxy-1-propene
• 英文别名: (Z)-2,3-bis(phenylthio)prop-2-en-1-ol；(Z)-2,3-diphenylthioprop-2-en-1-ol；(Z)-2,3-bis(phenylsulfanyl)prop-2-en-1-ol
• CAS: 137540-63-7
• 化学式: C₁₅H₁₄OS₂
• 分子量: 274.408
• InChiKey: GETNBRDORYHCHQ-QINSGFPZSA-N

物化性质

• 沸点：
  436.2±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-丙炔-1-醇 、 二苯二硫醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以80%的产率得到(Z)-1,2-bis(phenylthio)-3-hydroxy-1-propene
  参考文献：
  名称：

  通过将二硫化物和二硒化物加到末端炔烃上的高立体选择性一锅法制备双硫和三硫属元素化物烯烃

  摘要：

  我们在这里介绍在一个无催化剂的条件下，通过一锅法，二有机酰基二卤代二烃与末端炔烃的反应，以选择性地制备双硫和三硫属元素化物的烯烃，从而避免了先前制备硫属炔的过程。该反应在温和的反应条件下进行得很干净，并且向选择性炔烃中选择性地添加了二卤化双氰化物，只得到了相应的Z。异构体。我们观察到选择性控制是由炔丙醇中羟基的有效参与所决定的。另外，双硫属化物烯烃仅用具有酸性羟基质子的炔丙醇获得。相反，在炔丙基正子上没有潜在酸性羟基质子的炔烃仅产生三硫属元素化物烯烃。

  DOI：

  10.1021/jo050448o

文献信息

• Palladium-Catalyzed Carbonylative Lactonization of Propargyl Alcohols with Organic Dichalcogenides and Carbon Monoxide
  作者：Akiya Ogawa、Hitoshi Kuniyasu、Noboru Sonoda、Toshikazu Hirao

  DOI：10.1021/jo970973q

  日期：1997.11.1

  The reaction of propargylic alcohols with diaryl disulfides and carbon monoxide in the presence of tetrakis(triphenylphosphine)palladium leads to a novel thiolative lactonization to afford beta-(arylthio)-alpha,beta-unsaturated lactones in moderate to good yields. Similar conditions can be employed with homopropargylic alcohols, giving the corresponding delta-lactones with a beta-arylthio group successfully

  在四（三苯基膦）钯存在下，炔丙醇与二芳基二硫化物和一氧化碳的反应导致新的硫醇化内酯化，以中等至良好的产率提供β-（芳硫基）-α，β-不饱和内酯。均丙醇可以采用相似的条件，成功地得到相应的带有β-芳硫基的δ-内酯。使用二芳基二硒化物代替二芳基二硫化物的反应也获得了相似的一锅硫代/内酯化序列，从而提供了相应的β-硒代丁烯内酯（7）。
• The First Example of Polymer-Supported Palladium Catalyst for Stereo­selective S-S Bond Addition to Terminal Alkynes
  作者：Valentine Ananikov、Irina Beletskaya、Michael Kabeshov

  DOI：10.1055/s-2005-865195

  日期：——

  The polymer-supported recyclable palladium catalyst was prepared for stereoselective diaryl disulphides addition to terminal alkynes with high yields. The 96-98% product purity was achieved after filtering the polymer-supported catalyst without special purification procedure.

  制备了聚合物负载的可回收钯催化剂，用于以高产率将二芳基二硫化物立体选择性加成到末端炔烃上。过滤聚合物负载的催化剂后，无需特殊纯化程序即可获得 96-98% 的产品纯度。
• NMR approach for the identification of dinuclear and mononuclear complexes: The first detection of [Pd(SPh)2(PPh3)2] and [Pd2(SPh)4(PPh3)2] – The intermediate complexes in the catalytic carbon–sulfur bond formation reaction
  作者：Valentine P. Ananikov、Sergey S. Zalesskiy、Vadim V. Kachala、Irina P. Beletskaya

  DOI：10.1016/j.jorganchem.2010.10.012

  日期：2011.1

  analyzed the nature of palladium complexes in the catalytic system for selective carbon–sulfur bond formation via the addition of S–S and S–H bonds to alkynes. For the first time the mononuclear and dinuclear palladium complexes were clearly detected by DOSY NMR under the catalytic conditions. It was demonstrated that the concentration of these palladium complexes strongly depends on the amount of

  在本研究中，我们分析了通过向炔烃中添加S–S和S–H键，选择性形成碳硫键的催化体系中钯配合物的性质。在催化条件下，首次通过DOSY NMR可以清楚地检测到单核和双核钯配合物。已证明这些钯配合物的浓度强烈取决于反应条件下可用的膦配体的量。
• Addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex
  作者：Jianying Li、Jun Liu、Mingzhong Cai

  DOI：10.3184/030823409x12526892025829

  日期：2009.10

  2-bis(arylthio)-substituted alkenes have been conveniently synthesised in high yields by the stereoselective addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex. This polymeric palladium catalyst can be recovered and reused many times without any loss of activity.

  通过在 MCM-41 负载的双齿膦钯 (0) 配合物催化下，二芳基二硫化物立体选择性加成到末端炔烃上，可以方便地以高产率合成各种 (Z)-1,2-双(芳硫基)-取代的烯烃. 这种聚合钯催化剂可以回收和重复使用多次而不会损失任何活性。
• Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes
  作者：Hitoshi Kuniyasu、Akiya Ogawa、Shinichiro Miyazaki、Ilhyong Ryu、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1021/ja00026a013

  日期：1991.12

  Novel transition-metal-catalyzed reactions of disulfides and diselenides with acetylenes are described. In the of tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4], the (1) of diaryl disulfides and diselenides to terminal acetylenes 1 takes place stereoselectively to give high yields of (Z)-1,2-bis(arylthio)-1-alkenes 2 and (Z)-1,2-bis(arylseleno)-1-alkenes 3, respectively. A mechanistic proposal includes the following: (1) oxidative addition of (ArY)2 [Y = S, Se] to low-valent palladium species, (2) stereoselective cis-thiopalladation or cis-selenopalladation to acetylenes to form a cis-vinylpalladium intermediate, and (3) reductive elimination of the product with retention of the stereochemistry. When the reaction of diaryl disulfides and diselenides with terminal acetylenes is performed under the pressure of carbon monoxide, the carbonylative addition occurs to afford (Z)-1,3-bis(arylthio)-2-alken-1-ones 4 and (Z)-1,3-bis(arylseleno)-2-alken-1-ones 5, respectively. Carbon monoxide is regioselectively incorporated on the side of the terminal carbon of the acetylenes.