3,4-dimethyl-1-tosyl-2,3-dihydro-1 H-pyrrole | 1023888-51-8

• 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: 3,4-dimethyl-1-tosyl-2,3-dihydro-1 H-pyrrole
• 英文别名: 3,4-Dimethyl-1-(4-methylphenyl)sulfonyl-2,3-dihydropyrrole；3,4-dimethyl-1-(4-methylphenyl)sulfonyl-2,3-dihydropyrrole
• CAS: 1023888-51-8
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: HUVDCDZOZYKOAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二烯丙基-4-甲基苯磺酰胺 在 苄基三丁基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以99%的产率得到3,4-dimethyl-1-tosyl-2,3-dihydro-1 H-pyrrole
  参考文献：
  名称：

  Highly regioselective synthesis of N-acyl-2,3-dihydropyrrole or N-sulfonyl-2,3-dihydropyrrole derivatives by nano-palladium catalyzed cycloisomerization of 1,6-dienes

  摘要：

  Porous palladium nanoparticles were prepared using a solution-phase approach. Their structures and shapes were analyzed by XRD, EDS, TEM and HRTEM. These palladium nanoparticles were used to catalyze the cycloisomerization reaction of N,N-diallylamide or N,N-diallylsulfonamide, and N-acyl-23-dihydropyrrole or N-sulfonyl-2,3-dihydropyrrole derivatives were therefore synthesized with very high regioselectivity, and in good yields. The nano-palladium catalyst showed high efficiency and it can be reused several times. A hydropalladation mechanism was proposed for this reaction. (C) 2009 Published by Elsevier B.V.

  DOI：

  10.1016/j.catcom.2009.12.018

文献信息

• Palladium-catalyzed cascade reactions of benzyl halides with <i>N</i>,<i>N</i>-diallyl-<i>p</i>-toluenesulfonamide
  作者：Liansheng Wang、Yi Pan、Hongwen Hu

  DOI：10.1515/hc-2012-0090

  日期：2012.8.1

  Abstract Reaction of N,N-diallyl-p-toluenesulfonamide 1 with benzyl halides 2 in the presence of a palladium catalyst afforded a series of novel dihydropyrroles 3 in moderate yields. A palladium-catalyzed self-cyclization reaction of the diene 1 may take place to give a cyclic dihydropyrrole 4 during the reaction. It is proposed that the cyclic products 4 are formed via a palladium-catalyzed cascade

  摘要 N,N-二烯丙基-对甲苯磺酰胺 1 与苄基卤化物 2 在钯催化剂存在下反应，以中等产率得到一系列新型二氢吡咯 3。在反应过程中，可发生钯催化的二烯1的自环化反应，得到环状二氢吡咯4。建议通过钯催化的级联环化偶联过程形成环状产物4。苯基碘化物 5 与 1 在相同条件下反应得到正常的 Heck 乙烯基化产物 6。
• Catalytic cycloisomerisation of 1,6-dienes in ionic liquids
  作者：Xiaowei Miao、Joanna Feder-Kubis、Cédric Fischmeister、Juliusz Pernak、Pierre H. Dixneuf

  DOI：10.1016/j.tet.2008.02.016

  日期：2008.4

  The ruthenium and palladium catalysed cycloisomerisation of 1,6-dienes in [bdmim][PF6], a room temperature ionic liquid (RTIL), is presented. The catalytic system comprising of [RUCl2(COD)](n) in the presence of (PrOH)-Pr-i was found to be particularly efficient and selective for the cycloisomerisation of the N,N-diallyltosylamide. This system can be reused several times without loss of performances and displays catalytic activity after a long storage period in the 1L. (c) 2008 Elsevier Ltd. All rights reserved.
• Highly regioselective synthesis of N-acyl-2,3-dihydropyrrole or N-sulfonyl-2,3-dihydropyrrole derivatives by nano-palladium catalyzed cycloisomerization of 1,6-dienes
  作者：Lizhe Feng、Zhiyong Gan、Xiaopeng Nie、Peipei Sun、Jianchun Bao

  DOI：10.1016/j.catcom.2009.12.018

  日期：2010.2

  Porous palladium nanoparticles were prepared using a solution-phase approach. Their structures and shapes were analyzed by XRD, EDS, TEM and HRTEM. These palladium nanoparticles were used to catalyze the cycloisomerization reaction of N,N-diallylamide or N,N-diallylsulfonamide, and N-acyl-23-dihydropyrrole or N-sulfonyl-2,3-dihydropyrrole derivatives were therefore synthesized with very high regioselectivity, and in good yields. The nano-palladium catalyst showed high efficiency and it can be reused several times. A hydropalladation mechanism was proposed for this reaction. (C) 2009 Published by Elsevier B.V.