N-benzyl 4-cyclohexylidene-2-propylacrylamide | 463930-76-9

• 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 4-cyclohexylidene-2-propylacrylamide
• 英文别名: N-benzyl-2-(cyclohexylidenemethylidene)pentanamide
• CAS: 463930-76-9
• 化学式: C₁₉H₂₅NO
• 分子量: 283.414
• InChiKey: OIMWDLUFRFDTSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  4-碘苯甲酸甲酯 、 N-benzyl 4-cyclohexylidene-2-propylacrylamide 在 四(三苯基膦)钯 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 44.0h， 以100%的产率得到N-benzyl (4-(4-methoxycarbonylphenyl)-3-propyl-1-oxa-spiro[4,5]dec-3-enylidene) amine
  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
• 作为产物：
  描述：

  苄胺 、 2-Cyclohexylidenemethylene-pentanoic 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74%的产率得到N-benzyl 4-cyclohexylidene-2-propylacrylamide
  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

• 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.