5-Hydroxy-2-<(E)-propenyl-4-pyron> | 63861-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-Hydroxy-2-<(E)-propenyl-4-pyron>
• 英文别名: 5-hydroxy-2-[(E)-prop-1-enyl]pyran-4-one
• CAS: 63861-25-6
• 化学式: C₈H₈O₃
• 分子量: 152.15
• InChiKey: SUYMHOZDEDMBAV-NSCUHMNNSA-N

物化性质

• 沸点：
  325.9±42.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-2-<(E)-propenyl-4-pyron> 在 吡啶 、 六甲基二锡 、 palladium diacetate 、 三苯基膦 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 3-deoxyfunicone
  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
• 作为产物：
  描述：

  (2-氯甲基)-5-羟基-4H-吡喃-4-酮 在 二环己烷并-18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 96.0h， 生成 5-Hydroxy-2-<(E)-propenyl-4-pyron>
  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

• [EN] PROCESS FOR THE SYNTHESIS OF FUNICONE ANALOGUES<br/>[FR] PROCÉDÉ POUR LA SYNTHÈSE D'ANALOGUES DE FUNICONE
  申请人：CONSIGLIO NAZIONALE RICERCHE

  公开号：WO2012042482A1

  公开（公告）日：2012-04-05

  The present invention relates to the synthesis of analogous compounds of funicone, some of which are not found in nature, which comprises the preparation of compounds having general formula (III) and (IV) and the subsequent coupling reaction of said compounds in dimethylformamide by means of carbon monoxide in the presence of palladium allyl chloride dimer, to obtain compounds having formula (V) (scheme 2).

  本发明涉及富尼康类似化合物的合成，其中一些化合物在自然界中找不到，包括制备具有一般式（III）和（IV）的化合物，然后在二甲基甲酰胺中通过一氧化碳在钯丙烯氯化二聚体存在下进行偶联反应，以获得具有式（V）的化合物（方案2）。