N-benzyl-3-methyl-N-prop-2-enylbut-2-enamide | 135979-18-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-benzyl-3-methyl-N-prop-2-enylbut-2-enamide
• CAS: 135979-18-9
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: LGHLUAVNBKCZDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-methyl-N-prop-2-enylbut-2-enamide 、 苯磺酰溴 在 六正丁基二锡 作用下， 以 乙腈 为溶剂， 以62%的产率得到N-benzyl-4-<(phenylsulfonyl)methyl>-3-isopropylidene-2-pyrrolidone
  参考文献：
  名称：

  Chemoselective Lactam Formation in the Addition of Benzenesulfonyl Bromide to N-Allyl Acrylamides and N-Allyl 3,3-Dimethylacrylamides

  摘要：

  Chemoselectivity in the addition and cyclization reactions of PhSO2Br to N-allyl acrylamides has been confirmed due to the higher reactivity of the acrylic C=C bond toward the sulfonyl radical than that of the allyl C=C bond. Formation of gamma-lactams by C-beta-->C-alpha, cyclization can be achieved with N-allyl 3,3-dimethylacrylamides.

  DOI：

  10.1021/jo9820770

文献信息

• The free radical cyclization reaction of 1,6-dienes with allylsulfones
  作者：Che-Ping Chuang

  DOI：10.1016/s0040-4020(01)80976-5

  日期：1991.7

  A sulfonyl radical induced addition-cyclization reaction of 1,6-dienes with allylsulfones giving functionalized cyclopentane systems is described.
• Chemoselective Lactam Formation in the Addition of Benzenesulfonyl Bromide to <i>N</i>-Allyl Acrylamides and <i>N</i>-Allyl 3,3-Dimethylacrylamides
  作者：Chen Wang、Glen A. Russell

  DOI：10.1021/jo9820770

  日期：1999.4.1

  Chemoselectivity in the addition and cyclization reactions of PhSO2Br to N-allyl acrylamides has been confirmed due to the higher reactivity of the acrylic C=C bond toward the sulfonyl radical than that of the allyl C=C bond. Formation of gamma-lactams by C-beta-->C-alpha, cyclization can be achieved with N-allyl 3,3-dimethylacrylamides.