3-(1-methylene-2,2-bis(ethoxycarbonyl)propyl)-5-hexen-2-one

• 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: 3-(1-methylene-2,2-bis(ethoxycarbonyl)propyl)-5-hexen-2-one
• 英文别名: Diethyl 2-(3-acetylhexa-1,5-dien-2-yl)-2-methylpropanedioate；diethyl 2-(3-acetylhexa-1,5-dien-2-yl)-2-methylpropanedioate
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: QPBCUGNKAQPWAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  甲基丙二酸二乙酯 、 3-allylpenta-3,4-dien-2-one 在 potassium tert-butylate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以83%的产率得到3-(1-methylene-2,2-bis(ethoxycarbonyl)propyl)-5-hexen-2-one
  参考文献：
  名称：

  Studies on t-BuOK-catalyzed Michael addition of 1,2-allenic ketones with 2-substituted diethyl malonates: highly selective synthesis of β,γ-unsaturated enones

  摘要：

  In this paper, we have demonstrated a facile nucleophilic addition of 2-substituted diethyl malonate to various substituted 1,2-allenic ketones to afford beta,gamma-unsaturated enones using a catalytic amount of t-BuOK as the base. The reaction usually completes within 10 min in acetone at room temperature. The stereoselectivity of the reaction with gamma-substituted allenic ketones is very high affording the beta,gamma-unsaturated E-enones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.131

文献信息

• Studies on t-BuOK-catalyzed Michael addition of 1,2-allenic ketones with 2-substituted diethyl malonates: highly selective synthesis of β,γ-unsaturated enones
  作者：Shengming Ma、Shichao Yu、Wenjian Qian

  DOI：10.1016/j.tet.2005.01.131

  日期：2005.4

  In this paper, we have demonstrated a facile nucleophilic addition of 2-substituted diethyl malonate to various substituted 1,2-allenic ketones to afford beta,gamma-unsaturated enones using a catalytic amount of t-BuOK as the base. The reaction usually completes within 10 min in acetone at room temperature. The stereoselectivity of the reaction with gamma-substituted allenic ketones is very high affording the beta,gamma-unsaturated E-enones. (c) 2005 Elsevier Ltd. All rights reserved.