3-fluorophenyl vinyl sulfide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-fluorophenyl vinyl sulfide
• 英文别名: 1-Ethenylsulfanyl-3-fluorobenzene
• 化学式: C₈H₇FS
• 分子量: 154.208
• InChiKey: AWWRVUGTQDIVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• 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：
  2

反应信息

• 作为反应物：
  描述：

  3-fluorophenyl vinyl sulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以3.62 g的产率得到(m-F)-phenyl vinyl sulfoxide
  参考文献：
  名称：

  Hydrogenative Kinetic Resolution of Vinyl Sulfoxides

  摘要：

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).

  DOI：

  10.1021/acs.orglett.5b02139
• 作为产物：
  描述：

  3-氟苯硫酚 、 calcium carbide 在 水 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以88%的产率得到3-fluorophenyl vinyl sulfide
  参考文献：
  名称：

  以碳化钙为乙炔源的高效无金属合成乙烯基硫代酸酯的途径

  摘要：

  在标准实验室设置中，不容易进行涉及高压乙炔的化学反应。爆炸的危险和技术难题极大地使设备复杂化，并大大增加了成本。

  DOI：

  10.1039/c5gc01552a

文献信息

• Cr-Catalyzed Diastereo- and Enantioselective Synthesis of β-Hydroxy Sulfides and Selenides
  作者：Xiaowen Xia、Zhaobin Wang

  DOI：10.1021/acscatal.2c03271

  日期：2022.9.16

  The Cr-catalyzed Nozaki–Hiyama–Kishi reaction serves as a reliable and valuable C–C bond construction strategy in organic synthesis. However, known Cr-catalyzed asymmetric transformations are limited mainly to primary Cr intermediates with an α-substituted π-functional group, which impeded their further synthetic applications. Herein, we described a Cr-catalyzed three-component reaction, which provides

  Cr催化的Nozaki-Hiyama-Kishi反应是有机合成中可靠且有价值的C-C键构建策略。然而，已知的 Cr 催化的不对称转化主要限于具有 α-取代的 π-官能团的初级 Cr 中间体，这阻碍了它们进一步的合成应用。在这里，我们描述了一种 Cr 催化的三组分反应，它提供了对有价值的手性 β-羟基硫化物和具有邻位立体中心的硒化物的模块化访问。基于初步机理研究，该方法通过不对称还原自由基-极性交叉进行，具有由α-硫或硒稳定的前所未有的二级手性烷基Cr配合物。
• An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source
  作者：Konstantin S. Rodygin、Valentine P. Ananikov

  DOI：10.1039/c5gc01552a

  日期：——

  Chemical reactions involving high-pressure acetylene are not easily performed in a standard laboratory setup. The risk of explosion and technical difficulties drastically complicate the equipment and greatly increase the cost....

  在标准实验室设置中，不容易进行涉及高压乙炔的化学反应。爆炸的危险和技术难题极大地使设备复杂化，并大大增加了成本。
• Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
  作者：Joan R. Lao、Héctor Fernández-Pérez、Anton Vidal-Ferran

  DOI：10.1021/acs.orglett.5b02139

  日期：2015.8.21

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).