N-[2-cyano-1-(4-methoxyphenyl)prop-2-enyl]-4-methylbenzenesulfonamide | 212781-19-6

• 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-[2-cyano-1-(4-methoxyphenyl)prop-2-enyl]-4-methylbenzenesulfonamide
• CAS: 212781-19-6
• 化学式: C₁₈H₁₈N₂O₃S
• 分子量: 342.419
• InChiKey: XAUMKROSVMDHDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-cyano-1-(4-methoxyphenyl)prop-2-enyl]-4-methylbenzenesulfonamide 在 乙醛肟 、 水 、 palladium diacetate 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以83%的产率得到2-[(4-methoxyphenyl)-(toluene-4-sylfonylamino)methyl]-acrylamide
  参考文献：
  名称：

  Facile Synthesis of N-Tosyl Aza-Baylis-Hillman Adducts of Acrylamide via a Pd-Catalyzed Hydration of Nitrile to Amide

  摘要：

  DOI：

  10.5012/bkcs.2010.31.03.700
• 作为产物：
  描述：

  (E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfonamide 、 丙烯腈 在 hydroxyl ionic liquid-supported quinuclidine 作用下， 反应 4.0h， 以97%的产率得到N-[2-cyano-1-(4-methoxyphenyl)prop-2-enyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis–Hillman catalysis: synergistic effect of ionic liquids as organocatalyst supports

  摘要：

  Hydroxyl ionic liquid (HIL) has been explored as a novel support for Baylis-Hillman catalyst. The HIL-supported catalyst showed a better catalytic activity compared to other IL-immobilized catalyst that has no hydroxyl group attached to the IL scaffold. The hydroxyl group linked on IL played an important role in facilitating efficient catalysis under solvent-free conditions. The corresponding Baylis-Hillman and aza-Baylis-Hillman adducts were obtained in good to excellent yields in all cases examined. The HIL-supported quinuclidine can be readily recovered and reused for six times without significant loss of catalytic activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.045

文献信息

• Friedel-Crafts reaction of the Baylis-Hillman adducts of N -tosylimine derivatives
  作者：Hong Jung Lee、Mi Ra Seong、Jae Nyoung Kim

  DOI：10.1016/s0040-4039(98)01280-5

  日期：1998.8

  Friedel-Crafts reaction of aromatic compounds with the Baylis-Hillman adducts of N-tosylimine derivatives in the presence of sulfuric acid provided a stereoselective methodology for the preparation of 2-benzylsubstituted olefins in moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• The reaction of the Baylis-Hillman adducts of N-tosylimines with N,N-dimethylformamide dimethylacetal
  作者：Hong Jung Lee、Hyoung Shik Kim、Jae Nyoung Kim

  DOI：10.1016/s0040-4039(99)00749-2

  日期：1999.6

  The reaction of N,N-dimethylformamide dimethylacetal (DMF-DMA) and the Baylis-Hillman adducts of N-tosylimines afforded N-methyl-N-tosyl allylic amine derivatives stereoselectively in moderate yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis–Hillman catalysis: synergistic effect of ionic liquids as organocatalyst supports
  作者：Xueling Mi、Sanzhong Luo、Hui Xu、Long Zhang、Jin-Pei Cheng

  DOI：10.1016/j.tet.2005.12.045

  日期：2006.3

  Hydroxyl ionic liquid (HIL) has been explored as a novel support for Baylis-Hillman catalyst. The HIL-supported catalyst showed a better catalytic activity compared to other IL-immobilized catalyst that has no hydroxyl group attached to the IL scaffold. The hydroxyl group linked on IL played an important role in facilitating efficient catalysis under solvent-free conditions. The corresponding Baylis-Hillman and aza-Baylis-Hillman adducts were obtained in good to excellent yields in all cases examined. The HIL-supported quinuclidine can be readily recovered and reused for six times without significant loss of catalytic activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Facile Synthesis of N-Tosyl Aza-Baylis-Hillman Adducts of Acrylamide via a Pd-Catalyzed Hydration of Nitrile to Amide
  作者：Eun-Sun Kim、Yu-Mi Kim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2010.31.03.700

  日期：2010.3.20