N-tert-butyl-N-(3-methylbut-2-enyl)-acrylamide | 671184-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tert-butyl-N-(3-methylbut-2-enyl)-acrylamide
• 英文别名: N-tert-butyl-N-(3-methylbut-2-enyl)prop-2-enamide
• CAS: 671184-01-3
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: XIKFBIUNHPCICM-UHFFFAOYSA-N

物化性质

• 沸点：
  298.6±19.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 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-tert-butyl-N-(3-methylbut-2-enyl)-acrylamide 在 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 为溶剂， 反应 21.0h， 生成 1-(2,2-diethyl-butyryl)-1H-pyrrole-3-carboxylic acid N-tert-butyl-N-(3-methyl-but-2-enyl)amide
  参考文献：
  名称：

  Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

  摘要：

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

  DOI：

  10.1021/ol0364071
• 作为产物：
  描述：

  N-叔丁基丙烯酰胺 、 1-溴-3-甲基-2-丁烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以30%的产率得到N-tert-butyl-N-(3-methylbut-2-enyl)-acrylamide
  参考文献：
  名称：

  Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

  摘要：

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

  DOI：

  10.1021/ol0364071

文献信息

• Nucleophilic Addition to Electron-Rich Heteroaromatics:  Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides
  作者：Jonathan Clayden、Rachel Turnbull、Ivan Pinto

  DOI：10.1021/ol0364071

  日期：2004.2.1

  Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.