N-(4-methylphenyl)sulfonyl-N-undec-10-enoylundec-10-enamide | 1426264-44-9

• 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: N-(4-methylphenyl)sulfonyl-N-undec-10-enoylundec-10-enamide
• CAS: 1426264-44-9
• 化学式: C₂₉H₄₅NO₄S
• 分子量: 503.747
• InChiKey: QFUNWPHRODILQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-methylphenyl)sulfonyl-N-undec-10-enoylundec-10-enamide 在 second-generation Hoveyda-Grubbs catalyst supported on mesocellular siliceous foam with nanopores(> 7nm) 作用下， 以 十二烷 、 二氯甲烷 为溶剂， 反应 6.0h， 以35.484%的产率得到
  参考文献：
  名称：

  Highly Selective Macrocycle Formations by Metathesis Catalysts Fixated in Nanopores

  摘要：

  Ruthenium-based metathesis catalysts immobilized on mesocellular siliceous foam (MCF) bearing large nanopores proved highly efficient and selective for macrocyclic ring-closing metathesis (RCM). Kinetic studies revealed that the homogeneous counterpart exhibited far higher activity that accounted for more oligomerization pathways and resulted in less macrocyclization products. Meanwhile, the immobilized catalysts showed lower conversion rates leading to higher yields of macrocyclic products in a given reaction time, with conversion rates and yields dependent upon pore size, catalyst loading density, and linker length. The macrocycle formations via RCM were accelerated by increasing the pore size and decreasing the catalyst loading density while retaining the comparably high yield. The catalysts immobilized on MCF, of which silica surface is rigid and pores are relatively large, showed high conversion rates and yields compared with an analogue immobilized on TentaGel resins, of which backbone becomes flexible upon swelling in the reaction medium. It is noteworthy that the selectivity for the macrocyclic RCM can be significantly improved by tuning the catalyst initiation rates via immobilization onto the support materials in which well-defined three-dimentional network of large nanopores are deployed.

  DOI：

  10.1021/jo302823w
• 作为产物：
  描述：

  10-十一碳烯基氯酸 、 对甲苯磺酰胺 在 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以71%的产率得到N-(4-methylphenyl)sulfonyl-N-undec-10-enoylundec-10-enamide
  参考文献：
  名称：

  Highly Selective Macrocycle Formations by Metathesis Catalysts Fixated in Nanopores

  摘要：

  Ruthenium-based metathesis catalysts immobilized on mesocellular siliceous foam (MCF) bearing large nanopores proved highly efficient and selective for macrocyclic ring-closing metathesis (RCM). Kinetic studies revealed that the homogeneous counterpart exhibited far higher activity that accounted for more oligomerization pathways and resulted in less macrocyclization products. Meanwhile, the immobilized catalysts showed lower conversion rates leading to higher yields of macrocyclic products in a given reaction time, with conversion rates and yields dependent upon pore size, catalyst loading density, and linker length. The macrocycle formations via RCM were accelerated by increasing the pore size and decreasing the catalyst loading density while retaining the comparably high yield. The catalysts immobilized on MCF, of which silica surface is rigid and pores are relatively large, showed high conversion rates and yields compared with an analogue immobilized on TentaGel resins, of which backbone becomes flexible upon swelling in the reaction medium. It is noteworthy that the selectivity for the macrocyclic RCM can be significantly improved by tuning the catalyst initiation rates via immobilization onto the support materials in which well-defined three-dimentional network of large nanopores are deployed.

  DOI：

  10.1021/jo302823w

文献信息

• Highly Selective Macrocycle Formations by Metathesis Catalysts Fixated in Nanopores
  作者：Joo-Eun Jee、Jian Liang Cheong、Jaehong Lim、Cheng Chen、Soon Hyeok Hong、Su Seong Lee

  DOI：10.1021/jo302823w

  日期：2013.4.5

  Ruthenium-based metathesis catalysts immobilized on mesocellular siliceous foam (MCF) bearing large nanopores proved highly efficient and selective for macrocyclic ring-closing metathesis (RCM). Kinetic studies revealed that the homogeneous counterpart exhibited far higher activity that accounted for more oligomerization pathways and resulted in less macrocyclization products. Meanwhile, the immobilized catalysts showed lower conversion rates leading to higher yields of macrocyclic products in a given reaction time, with conversion rates and yields dependent upon pore size, catalyst loading density, and linker length. The macrocycle formations via RCM were accelerated by increasing the pore size and decreasing the catalyst loading density while retaining the comparably high yield. The catalysts immobilized on MCF, of which silica surface is rigid and pores are relatively large, showed high conversion rates and yields compared with an analogue immobilized on TentaGel resins, of which backbone becomes flexible upon swelling in the reaction medium. It is noteworthy that the selectivity for the macrocyclic RCM can be significantly improved by tuning the catalyst initiation rates via immobilization onto the support materials in which well-defined three-dimentional network of large nanopores are deployed.