4-[2-(2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)vinyl]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4-[2-(2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)vinyl]pyridine
• 英文别名: 4-[(E)-2-(2,3,5,6-tetrahydrofuro[3,2-f][1]benzofuran-4-yl)ethenyl]pyridine
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: AJBUNQDEKKXZPX-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 palladium diacetate 降冰片烯 、 氢碘酸 、 碘 、 叔丁基锂 、 potassium carbonate 、 caesium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 丙酮 、 正戊烷 为溶剂， 反应 60.08h， 生成 4-[2-(2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-yl)vinyl]pyridine
  参考文献：
  名称：

  Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence

  摘要：

  A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.

  DOI：

  10.1021/jo0617868

文献信息

• Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence
  作者：Dino Alberico、Alena Rudolph、Mark Lautens

  DOI：10.1021/jo0617868

  日期：2007.2.1

  A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.