5,6-epoxy-rapicone | 1375994-33-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-epoxy-rapicone
• 英文别名: Methyl 3,5-dimethoxy-2-(3-methyl-5-oxo-2,7-dioxabicyclo[4.1.0]hept-3-ene-6-carbonyl)benzoate；methyl 3,5-dimethoxy-2-(3-methyl-5-oxo-2,7-dioxabicyclo[4.1.0]hept-3-ene-6-carbonyl)benzoate
• CAS: 1375994-33-4
• 化学式: C₁₇H₁₆O₈
• 分子量: 348.309
• InChiKey: QZAXKRNRISNPHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Rapicone 在 lithium diisopropyl amide 、 硼酸三甲酯 、 双氧水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到5,6-epoxy-rapicone
  参考文献：
  名称：

  Chemical synthesis of funicone analogs

  摘要：

  Deoxyfunicone, rapicone and their 5,6-epoxy-derivatives are gamma-pyrone compounds with cytostatic and antiproliferative properties. Here we describe a synthesis of these compounds by carbonylative Stille coupling between kojic acid derivatives and functionalized iodo aryl compounds. The main advantages of this patent pending synthetic strategy lie in the simplicity and clean conversion of products, and in the possibility to obtain a high number of analogs by minor changes of the synthetic synthons. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.010

文献信息

• Chemical synthesis of funicone analogs
  作者：Emiliano Manzo、Maria Letizia Ciavatta

  DOI：10.1016/j.tet.2012.04.010

  日期：2012.6

  Deoxyfunicone, rapicone and their 5,6-epoxy-derivatives are gamma-pyrone compounds with cytostatic and antiproliferative properties. Here we describe a synthesis of these compounds by carbonylative Stille coupling between kojic acid derivatives and functionalized iodo aryl compounds. The main advantages of this patent pending synthetic strategy lie in the simplicity and clean conversion of products, and in the possibility to obtain a high number of analogs by minor changes of the synthetic synthons. (C) 2012 Elsevier Ltd. All rights reserved.