(E)-N-benzyl-N-tert-butyl-3-phenylacrylamide | 637034-43-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-benzyl-N-tert-butyl-3-phenylacrylamide
• 英文别名: N-benzyl-N-tert-butyl-3-phenylacrylamide；(E)-N-benzyl-N-tert-butyl-3-phenylprop-2-enamide
• CAS: 637034-43-6
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: SJVUGOCQTPSNCZ-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-N-benzyl-N-tert-butyl-3-phenylacrylamide 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 N-[2-(1-tert-butyl-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrol-3-yl)-2-phenyl-vinyl]-2,2-diethylbutyramide
  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-叔丁基苄胺 、 3-苯基-2-丙烯酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以99%的产率得到(E)-N-benzyl-N-tert-butyl-3-phenylacrylamide
  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

• β-Lactams or γ-lactams by 4-exo-trig or 5-endo-trig anionic cyclisation of lithiated acrylamide derivatives
  作者：Jonathan Clayden、David W. Watson、Madeleine Helliwell、Mark Chambers

  DOI：10.1039/b308029c

  日期：——

  Substituted acrylamide derivatives of benzylamine are lithiated α to nitrogen by LDA. The benzyllithium thus formed undergoes either 5-endo-trig anionic cyclisation, formally by intramolecular conjugate addition to the acrylamide, to yield 5-membered lactams, or, if the acrylamide bears a β-electron withdrawing group, 4-exo-trig cyclisation to a β-lactam.

  苄胺的丙烯酰胺衍生物被LDA锂化，在氮原子上形成β位。由此形成的苄基锂发生5-内型三阴离子环化反应，通过分子内共轭加成到丙烯酰胺上，生成5元内酰胺，或者，如果丙烯酰胺带有β-电子吸引基团，则发生4-外型三环化反应，生成β-内酰胺。
• 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.