3-methylbut-2-enoic acid diallylamide | 82799-51-7

• 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: 3-methylbut-2-enoic acid diallylamide
• 英文别名: N,N-diallyl-3-methylcrotonamide；3-methyl-N,N-bis(prop-2-enyl)but-2-enamide
• CAS: 82799-51-7
• 化学式: C₁₁H₁₇NO
• mdl: MFCD28577762
• 分子量: 179.262
• InChiKey: KNLTZPKKNGLQDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.3±29.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.363
• 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：

  苯磺酰溴 、 3-methylbut-2-enoic acid diallylamide 以 乙腈 为溶剂， 以34%的产率得到N-allyl-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
• 作为产物：
  描述：

  2-bromo-3-methyl-N,N-bis(prop-2-enyl)but-2-enamide 在 异丙基溴化镁 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到3-methylbut-2-enoic acid diallylamide
  参考文献：
  名称：

  Preparation of α-functionalized alkenylmagnesium reagents via a halide–magnesium exchange

  摘要：

  A general preparation of alkenylmagnesium derivatives bearing an electron-withdrawing function in the alpha-position (Y=CN, CO2R, CONR2, SO2Ph) has been made possible by using a low temperature (-40 to -30degreesC) bromine-magnesium exchange with i-PrMgBr in THF. This reaction has also been used to prepare 5-magnesiated-1,3-dioxin-4-one derivatives bearing an alkoxy substituent in beta-position to the carbon-magnesium bond. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00439-8

文献信息

• Naito, Takeaki; Honda, Yuko; Miyata, Okiko, Journal of the Chemical Society. Perkin transactions I, 1995, # 1, p. 19 - 26
  作者：Naito, Takeaki、Honda, Yuko、Miyata, Okiko、Ninomiya, Ichiya

  DOI：——

  日期：——
• Preparation of α-functionalized alkenylmagnesium reagents via a halide–magnesium exchange
  作者：Jérôme Thibonnet、Viet Anh Vu、Laurent Bérillon、Paul Knochel

  DOI：10.1016/s0040-4020(02)00439-8

  日期：2002.6

  A general preparation of alkenylmagnesium derivatives bearing an electron-withdrawing function in the alpha-position (Y=CN, CO2R, CONR2, SO2Ph) has been made possible by using a low temperature (-40 to -30degreesC) bromine-magnesium exchange with i-PrMgBr in THF. This reaction has also been used to prepare 5-magnesiated-1,3-dioxin-4-one derivatives bearing an alkoxy substituent in beta-position to the carbon-magnesium bond. (C) 2002 Published by Elsevier Science Ltd.
• 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.