3-乙基-3,4-戊二烯-2-酮 | 39579-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙基-3,4-戊二烯-2-酮
• 英文名称: 3-ethylpenta-3,4-dien-2-one
• 英文别名: 3-Ethyl-3,4-pentadien-2-one
• CAS: 39579-60-7
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: YMFQRIBQAALKII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  2-benzoyl-3-phenylacrylonitrile 、 3-乙基-3,4-戊二烯-2-酮 在 N-[(1S)-1-[(二苯膦基)甲基]-2-甲基丙基]-3,5-二(三氟甲基)苯甲酰胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以92%的产率得到(E)-2-(3-oxopentan-2-ylidene)-4,6-diphenyl-3,4-dihydro-2H-pyran-5-carbonitrile
  参考文献：
  名称：

  氨基酸衍生的膦所催化的对映选择性[4 + 2]-环戊二烯和异戊二烯的合成：官能化的二氢吡喃类化合物的合成

  摘要：

  建立了氰基活化的二氧杂环丁烯与烯丙基之间的对映选择性[4 + 2]环化过程。一升-缬氨酸衍生膦是催化反应高效，并且以高产率和具有优异的对映选择性制备一个宽范围的高度功能的二氢吡喃。

  DOI：

  10.1021/acs.orglett.6b00760

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.
• K₂CO₃-Catalyzed Michael Addition−Lactonization Reaction of 1,2-Allenyl Ketones with Electron-Withdrawing Group Substituted Acetates. An Efficient Synthesis of α-Pyrone Derivatives
  作者：Shengming Ma、Shaohu Yin、Lintao Li、Fenggang Tao

  DOI：10.1021/ol0170859

  日期：2002.2.1

  alpha-Pyrone derivatives were synthesized via the base catalyzed or promoted reaction of 1,2-allenyl ketones and electron-withdrawing group substituted acetates. The reaction was believed to proceed through a Michael addition C-C double-bond migration-lactonization process.