4-cyclohexylbuta-2,3-dienoyl chloride | 1027566-18-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 4-cyclohexylbuta-2,3-dienoyl chloride
• CAS: 1027566-18-2
• 化学式: C₁₀H₁₃ClO
• 分子量: 184.666
• InChiKey: NTDXYZKJZXCNLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-cyclohexylbuta-2,3-dienoyl chloride 在 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-benzyl-5-c-hexyl-5-hydroxy-4-phenylpyrrol-2(5H)-one
  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：

  4-cyclohexylbuta-2,3-dienoic acid 在 氯化亚砜 作用下， 反应 0.5h， 生成 4-cyclohexylbuta-2,3-dienoyl chloride
  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.