6-isopropyl-3-(methoxycarbonyl)-4-phenyl-2-pyrone | 136840-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-isopropyl-3-(methoxycarbonyl)-4-phenyl-2-pyrone
• 英文别名: Methyl 2-oxo-4-phenyl-6-propan-2-ylpyran-3-carboxylate
• CAS: 136840-23-8
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: TWNLILYWIYUPNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methyl-1-phenylpent-1-yn-3-one 、 丙二酸二甲酯 在 sodium hydride 作用下， 生成 6-isopropyl-3-(methoxycarbonyl)-4-phenyl-2-pyrone
  参考文献：
  名称：

  Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 2. Reactions with malonate anion. Concerning the mechanism of the Favorskii rearrangement

  摘要：

  The scope and limiations of the reaction of alpha'-nucleofuge alpha,beta-unsaturated ketones with sodium dimethyl malonate has been studied systematically. The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction. In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold. Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.

  DOI：

  10.1021/jo00024a015

文献信息

• Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 2. Reactions with malonate anion. Concerning the mechanism of the Favorskii rearrangement
  作者：Thomas R. Barbee、Hedeel Guy、Mary Jane Heeg、Kim F. Albizati

  DOI：10.1021/jo00024a015

  日期：1991.11

  The scope and limiations of the reaction of alpha'-nucleofuge alpha,beta-unsaturated ketones with sodium dimethyl malonate has been studied systematically. The substrates with good nucleofuges (halides, mesylate) give cyclopropanols upon reaction with malonate anion by way of a conjugate Favorskii reaction. In reactions with substrates containing the poorer nucleofuge (acetoxy) conjugate addition proceeded without entering the Favorskii manifold. Concerning the mechanism of the Favorskii reaction, it is suggested that the loss of the nucleofuge occurs to give a 2-oxyallyl cation, but that disrotatory ring closure is facile and the only products observed result from nucleophilic trapping of cyclopropanones to yield cyclopropanols in fair to good yield.