4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide | 824390-89-8

• 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: 4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide
• 英文别名: Benzenesulfonamide, N-[1-(3-bromophenyl)-2-propenyl]-4-methyl-；N-[1-(3-bromophenyl)prop-2-enyl]-4-methylbenzenesulfonamide
• CAS: 824390-89-8
• 化学式: C₁₆H₁₆BrNO₂S
• 分子量: 366.279
• InChiKey: OMASEGPAKIYAQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide 在 dimethyl sulfide borane 、 sodium hydroxide 、 乙醇 、 双氧水 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以70%的产率得到2-(3-bromophenyl)-1-(toluene-4-sulfonyl)-azetidine
  参考文献：
  名称：

  2-Aryl-N-tosylazetidines as Formal 1,4-Dipoles for [4 + 2] Cycloaddition Reactions with Nitriles:  An Easy Access to the Tetrahydropyrimidine Derivatives

  摘要：

  [Graphics]A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitriles in the presence of BF3.OEt2 has been described for the synthesis of substituted tetrahydropyrimidines. It is proposed that the reaction proceeds in Ritter fashion.

  DOI：

  10.1021/ol048161l
• 作为产物：
  描述：

  乙烯基氯化镁 、 (E)-N-(3-溴苯亚甲基)-4-甲基苯磺酰胺 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.0h， 以90%的产率得到4-methyl-N-(1-(3-bromophenyl)-allyl)-benzenesulfonamide
  参考文献：
  名称：

  2-Aryl-N-tosylazetidines as Formal 1,4-Dipoles for [4 + 2] Cycloaddition Reactions with Nitriles:  An Easy Access to the Tetrahydropyrimidine Derivatives

  摘要：

  [Graphics]A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitriles in the presence of BF3.OEt2 has been described for the synthesis of substituted tetrahydropyrimidines. It is proposed that the reaction proceeds in Ritter fashion.

  DOI：

  10.1021/ol048161l

文献信息

• 2-Aryl-<i>N</i>-tosylazetidines as Formal 1,4-Dipoles for [4 + 2] Cycloaddition Reactions with Nitriles:  An Easy Access to the Tetrahydropyrimidine Derivatives
  作者：B. A. Bhanu Prasad、Alakesh Bisai、Vinod K. Singh

  DOI：10.1021/ol048161l

  日期：2004.12.1

  [Graphics]A new synthetic route to 2-aryl-N-tosyl azetidines has been developed starting from N-tosylarylaldimines in two steps in an overall yield of 63-70%. A formal [4 + 2] cycloaddition of these 2-aryl-N-tosylazetidines with nitriles in the presence of BF3.OEt2 has been described for the synthesis of substituted tetrahydropyrimidines. It is proposed that the reaction proceeds in Ritter fashion.