(E)-1-((phenylsulfonyl)methyl)-4-(2-(phenylsulfonyl)vinyl)benzene | 1426679-22-2

• 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: (E)-1-((phenylsulfonyl)methyl)-4-(2-(phenylsulfonyl)vinyl)benzene
• 英文别名: 1-[(E)-2-(benzenesulfonyl)ethenyl]-4-(benzenesulfonylmethyl)benzene
• CAS: 1426679-22-2
• 化学式: C₂₁H₁₈O₄S₂
• 分子量: 398.504
• InChiKey: YMVBTGAGHCBVFC-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环己基硼酸 、 (E)-1-((phenylsulfonyl)methyl)-4-(2-(phenylsulfonyl)vinyl)benzene 在 potassium phosphate 、 Ir[dF(CF₃)ppy]2(dtbbpy)PF₆ 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 36.0h， 以87%的产率得到1-(2-cyclohexylvinyl)-4-((phenylsulfonyl)methyl)benzene
  参考文献：
  名称：

  无需外部路易斯碱作为活化剂的可见光介导的烷基硼酸的烯基化

  摘要：

  本文中，我们报告了一种在室温下直接可见光介导的烷基硼酸烯基化的方案，而无需使用外部路易斯碱作为活化剂，并且我们提出了一种涉及烷基烷基硼酸的苯磺酸盐活化的机理。该协议允许使用各种烯基砜有效地官能化各种环状和无环伯和仲烷基硼酸。我们通过制备或功能化多种药物和天然产品证明了其实用性。

  DOI：

  10.1021/acs.orglett.1c00399
• 作为产物：
  描述：

  4-氯甲基苯乙烯 、 sodium benzenesulfonate 在 碘 、 sodium acetate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到(E)-1-((phenylsulfonyl)methyl)-4-(2-(phenylsulfonyl)vinyl)benzene
  参考文献：
  名称：

  An Improved Synthesis of Vinyl- and β-Iodovinyl Sulfones by a Molecular Iodine-Mediated One-Pot Iodosulfonation-Dehydroiodination Reaction

  摘要：

  An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective -iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation.

  DOI：

  10.1080/00397911.2012.663448

文献信息

• An Improved Synthesis of Vinyl- and β-Iodovinyl Sulfones by a Molecular Iodine-Mediated One-Pot Iodosulfonation-Dehydroiodination Reaction
  作者：Tassaporn Sawangphon、Praewpan Katrun、Korbua Chaisiwamongkhol、Manat Pohmakotr、Vichai Reutrakul、Thaworn Jaipetch、Darunee Soorukram、Chutima Kuhakarn

  DOI：10.1080/00397911.2012.663448

  日期：2013.6.18

  An improved one-pot method to synthesize vinyl sulfones from unsaturated systems by using molecular iodine/sodium arenesulfinate/sodium acetate as reagents was described. Vinyl sulfones derived from styrene derivatives were generally obtained in good to excellent yields except for those bearing strong electron releasing substituent. Aliphatic alkenes and activated alkenes gave the corresponding vinyl sulfone products in moderate to good yields. Arylacetylenes yielded the respective -iodovinyl sulfones in good yields while low yield was observed with aliphatic terminal alkyne. The potentials of the method entail simplicity, short reaction time, non-anhydrous reaction conditions, employing inexpensive, non-metallic reagent and integrating two reactions that are commonly accomplished separately into a single operation.
• Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator
  作者：Fuyang Yue、Jianyang Dong、Yuxiu Liu、Qingmin Wang

  DOI：10.1021/acs.orglett.1c00399

  日期：2021.4.2

  Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with

  本文中，我们报告了一种在室温下直接可见光介导的烷基硼酸烯基化的方案，而无需使用外部路易斯碱作为活化剂，并且我们提出了一种涉及烷基烷基硼酸的苯磺酸盐活化的机理。该协议允许使用各种烯基砜有效地官能化各种环状和无环伯和仲烷基硼酸。我们通过制备或功能化多种药物和天然产品证明了其实用性。