3-hexylpenta-3,4-dien-2-one | 75111-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hexylpenta-3,4-dien-2-one
• 英文别名: 3-acetyl-1,2-nonadiene
• CAS: 75111-00-1
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: YVDSYYYQLQKOSL-UHFFFAOYSA-N

物化性质

• 沸点：
  251.7±7.0 °C(Predicted)
• 密度：
  0.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  3-hexylpenta-3,4-dien-2-one 、 丙二酸二乙酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以81%的产率得到3-(ethoxycarbonyl)-4,6-dimethyl-5-hexyl-2-pyranone
  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
• 作为产物：
  描述：

  3-hexyl-2,4-pentanedione 在 溴 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 23.0h， 生成 3-hexylpenta-3,4-dien-2-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

• The preparation of a terminal allene, 3-haloallene and 3-acylallene from a propargyltrimethylsilane
  作者：P. E. Peterson、T. A. Flood

  DOI：10.1021/jo01312a046

  日期：1980.11
• FLOOD T.; PETERSON P. E., J. ORG. CHEM., 1980, 45, NO 24, 5006-5007
  作者：FLOOD T.、 PETERSON P. E.

  DOI：——

  日期：——
• 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.