10-((E)-2-methoxycarbonylvinyl)-9-propyl-6H-dibenzo[b,d]pyran-6-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 10-((E)-2-methoxycarbonylvinyl)-9-propyl-6H-dibenzo[b,d]pyran-6-one
• 英文别名: methyl (E)-3-(6-oxo-9-propylbenzo[c]chromen-10-yl)prop-2-enoate
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: JQFCLBOKFVPRPT-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-戊炔 、 methyl (Z)-5-[2-[(Z)-3-bromoprop-2-enoyl]oxyphenyl]pent-2-en-4-ynoate 在 copper(l) iodide 、 四(三苯基膦)钯 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以42%的产率得到10-((E)-2-methoxycarbonylvinyl)-9-propyl-6H-dibenzo[b,d]pyran-6-one
  参考文献：
  名称：

  Synthesis of 6H-Dibenzo[b,d]pyran-6-ones from Aryl 3-Bromopropenoates via a Sequential One-Pot Procedure Using the Sonogashira Coupling−Benzannulation Reaction

  摘要：

  Various kinds of 6H-dibenzo [b,d] pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which the ortho-position of aryl group is substituted with enynes or iodine, with acetylenes 2 in the presence of palladium and copper catalysts. The Sonogashira coupling between the aryl 3-bromopropenoates 1a and 1b, bearing enynes at the ortho-position of aryl group, and alkynes 2a-g gave the enyne intermediates 3 in situ, which subsequently underwent the palladium-catalyzed benzannulation reaction to afford the 6H-dibenzo [b,d] pyran-6-ones 5a-g and 6. The Sonogashira coupling between the aryl 3-bromopropenoate le, bearing iodine at the ortho-position of aryl group, and diynes 2f and 2h produced the diyne intermediates 13, which underwent the benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 14f and 14h.

  DOI：

  10.1021/jo025659x

文献信息

• Synthesis of 6<i>H</i>-Dibenzo[<i>b</i>,<i>d</i>]pyran-6-ones from Aryl 3-Bromopropenoates via a Sequential One-Pot Procedure Using the Sonogashira Coupling−Benzannulation Reaction
  作者：Taishi Kawasaki、Yoshinori Yamamoto

  DOI：10.1021/jo025659x

  日期：2002.7.1

  Various kinds of 6H-dibenzo [b,d] pyran-6-ones 4 were synthesized via a sequential one-pot procedure using the Sonogashira coupling-benzannulation reaction of aryl 3-bromopropenoates 1, in which the ortho-position of aryl group is substituted with enynes or iodine, with acetylenes 2 in the presence of palladium and copper catalysts. The Sonogashira coupling between the aryl 3-bromopropenoates 1a and 1b, bearing enynes at the ortho-position of aryl group, and alkynes 2a-g gave the enyne intermediates 3 in situ, which subsequently underwent the palladium-catalyzed benzannulation reaction to afford the 6H-dibenzo [b,d] pyran-6-ones 5a-g and 6. The Sonogashira coupling between the aryl 3-bromopropenoate le, bearing iodine at the ortho-position of aryl group, and diynes 2f and 2h produced the diyne intermediates 13, which underwent the benzannulation reaction to afford the 6H-dibenzo[b,d]pyran-6-ones 14f and 14h.