(E)-2-butyl-3-(1',1'-bis(ethoxycarbonyl)methyl)-1-phenyl-3-nonen-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-butyl-3-(1',1'-bis(ethoxycarbonyl)methyl)-1-phenyl-3-nonen-1-one
• 英文别名: diethyl 2-[(E)-5-benzoyldodec-6-en-6-yl]propanedioate
• 化学式: C₂₆H₃₈O₅
• 分子量: 430.585
• InChiKey: DGCBAJDUGXUXAI-XUTLUUPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-二甲基苯甲酰胺 在 potassium carbonate 作用下， 以 四氢呋喃 、 环己烷 、 丙酮 为溶剂， 反应 72.0h， 生成 (E)-2-butyl-3-(1',1'-bis(ethoxycarbonyl)methyl)-1-phenyl-3-nonen-1-one
  参考文献：
  名称：

  Studies on K₂CO₃-Catalyzed 1,4-Addition of 1,2-Allenic Ketones with Diethyl Malonate:  Controlled Selective Synthesis of β,γ-Unsaturated Enones and α-Pyrones

  摘要：

  The K2CO3 (10 mol %)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized beta,gamma-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-allenyl ketones, the highly selective formation of beta,gamma-unsaturated enones 4 was observed; with 1,2-allenyl ketones bearing one or two 3-substituents in the allenyl group, only beta,gamma-unsaturated enones 3 with an immigrated carbon-carbon double bond were produced; with 3-monosubstituted-1,2-allenyl ketones Z-beta,gamma-unsaturated enones 3 were formed with excellent stereoselectivity (E:Z > 96:4); with propadienyl ketones, mixtures of beta,gamma-unsaturated enones 3 and 4 were formed. alpha-Pyrone derivatives were synthesized via the K2CO3-catalyzed or -promoted reaction of 1,2-allenic ketones with diethyl malonate via a sequential Michael addition-carbon-carbon double bond migration-lactonization process.

  DOI：

  10.1021/jo034633i

文献信息

• Studies on K₂CO₃-Catalyzed 1,4-Addition of 1,2-Allenic Ketones with Diethyl Malonate:  Controlled Selective Synthesis of β,γ-Unsaturated Enones and α-Pyrones
  作者：Shengming Ma、Shichao Yu、Shaohu Yin

  DOI：10.1021/jo034633i

  日期：2003.11.1

  The K2CO3 (10 mol %)-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones leading to polyfunctionalized beta,gamma-unsaturated enones 3 or 4 was studied. With 3-unsubstituted 1-substituted-1,2-allenyl ketones, the highly selective formation of beta,gamma-unsaturated enones 4 was observed; with 1,2-allenyl ketones bearing one or two 3-substituents in the allenyl group, only beta,gamma-unsaturated enones 3 with an immigrated carbon-carbon double bond were produced; with 3-monosubstituted-1,2-allenyl ketones Z-beta,gamma-unsaturated enones 3 were formed with excellent stereoselectivity (E:Z > 96:4); with propadienyl ketones, mixtures of beta,gamma-unsaturated enones 3 and 4 were formed. alpha-Pyrone derivatives were synthesized via the K2CO3-catalyzed or -promoted reaction of 1,2-allenic ketones with diethyl malonate via a sequential Michael addition-carbon-carbon double bond migration-lactonization process.