N-benzyl 2-benzyl-4-methyl-2,3-pentadienamide | 314761-76-7

• 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: N-benzyl 2-benzyl-4-methyl-2,3-pentadienamide
• 英文别名: N-benzyl 2-benzyl-4-methylpenta-2,3-dienamide；N,2-dibenzyl-4-methylpenta-2,3-dienamide
• CAS: 314761-76-7
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: KIPJFZDKCNGTFU-UHFFFAOYSA-N

物化性质

• 沸点：
  517.9±50.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-benzyl 2-benzyl-4-methyl-2,3-pentadienamide 在 CuCl₂*2H₂O 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到(Z)-2-benzylimino-3-benzyl-4-chloro-5,5-dimethyl-2,5-dihydrofuran
  参考文献：
  名称：

  Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides

  摘要：

  The reactions of 4-mono- or 4-unsubstituted 2,3-alkadienamides with CuX2 afforded 5-hydroxypyrTol-2(5H)-ones via the sequential lactamization and gamma-hydroxylation process in aqueous THF while those of 4,4-disubstituted 2,3-alkadienamides with CuX2 in THF afforded iminolactones in high yields. Iodoiminolactonization and iodolactamization/gamma-hydroxylation were achieved by the corresponding reaction with I-2 in THF at rt. The structures of the products depend on the steric hindrance at the 4-position of the starting allenamides. Relatively electron-rich allenes afforded the corresponding products in much higher yields under milder reaction conditions implying the intramolecular electrophilic nature of the cyclization reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.050
• 作为产物：
  描述：

  苄胺 、 2-benzyl-4-methylpenta-2,3-dienoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以55%的产率得到N-benzyl 2-benzyl-4-methyl-2,3-pentadienamide
  参考文献：
  名称：

  Steric Hindrance-Controlled Pd(0)-Catalyzed Coupling−Cyclization of 2,3-Allenamides and Organic Iodides. An Efficient Synthesis of Iminolactones and γ-Hydroxy-γ-lactams

  摘要：

  Under the catalysis of 1 mol % Pd(PPh3)(4), the reaction of 4,4-disubstituted 2,3-allenamides and organic iodides in toluene afforded iminolactones stereospecifically in >90% yields using K2CO3 (2 equiv)-5 mol % TBAB as the base. A similar reaction with 4-monosubstituted 2,3-allenamides afforded gamma-hydroxy-gamma-lactams in relatively lower yields. The N/O-attack selectivity may be determined by the steric effect at the 4-position of 2,3-allenamides.

  DOI：

  10.1021/jo025967v

文献信息

• Unexpected Facile Sequential Halolactamization−Hydroxylation of 2,3-Allenamides with CuX₂ for the Efficient Synthesis of 4-Halo-5-hydroxypyrrol-2(5<i>H</i>)-ones
  作者：Shengming Ma、Hexin Xie

  DOI：10.1021/ol006504j

  日期：2000.11.1

  [GRAPHICS]4-Halo-5-hydroxypyrrol-2(5H)-ones were synthesized from the efficient sequential halolactamization-hydroxylation reaction of 4-monosubstituted 2,3-allenamides with CuX2 (X = Br, CI) in high yields. Halolactamization of fully substituted 2,3-dienamide (1f) afforded 4-halo-pyrrol-2(5H)-ones.
• Steric Hindrance-Controlled Pd(0)-Catalyzed Coupling−Cyclization of 2,3-Allenamides and Organic Iodides. An Efficient Synthesis of Iminolactones and γ-Hydroxy-γ-lactams
  作者：Shengming Ma、Hexin Xie

  DOI：10.1021/jo025967v

  日期：2002.9.1

  Under the catalysis of 1 mol % Pd(PPh3)(4), the reaction of 4,4-disubstituted 2,3-allenamides and organic iodides in toluene afforded iminolactones stereospecifically in >90% yields using K2CO3 (2 equiv)-5 mol % TBAB as the base. A similar reaction with 4-monosubstituted 2,3-allenamides afforded gamma-hydroxy-gamma-lactams in relatively lower yields. The N/O-attack selectivity may be determined by the steric effect at the 4-position of 2,3-allenamides.
• Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides
  作者：Shengming Ma、Hexin Xie

  DOI：10.1016/j.tet.2004.10.050

  日期：2005.1

  The reactions of 4-mono- or 4-unsubstituted 2,3-alkadienamides with CuX2 afforded 5-hydroxypyrTol-2(5H)-ones via the sequential lactamization and gamma-hydroxylation process in aqueous THF while those of 4,4-disubstituted 2,3-alkadienamides with CuX2 in THF afforded iminolactones in high yields. Iodoiminolactonization and iodolactamization/gamma-hydroxylation were achieved by the corresponding reaction with I-2 in THF at rt. The structures of the products depend on the steric hindrance at the 4-position of the starting allenamides. Relatively electron-rich allenes afforded the corresponding products in much higher yields under milder reaction conditions implying the intramolecular electrophilic nature of the cyclization reaction. (C) 2004 Elsevier Ltd. All rights reserved.