3-(2,3,4,5,7,8,9,10-octahydro-1,11-dioxabenzo[1,2;4,5]dicyclohepten-6-yl)acrylic acid tert-butyl ester

• 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: 3-(2,3,4,5,7,8,9,10-octahydro-1,11-dioxabenzo[1,2;4,5]dicyclohepten-6-yl)acrylic acid tert-butyl ester
• 英文别名: tert-butyl (E)-3-(4,16-dioxatricyclo[9.5.0.03,9]hexadeca-1(11),2,9-trien-10-yl)prop-2-enoate
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: FRQRENNRXVXKBZ-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

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 、 丁酮 、 正戊烷 为溶剂， 反应 48.17h， 生成 3-(2,3,4,5,7,8,9,10-octahydro-1,11-dioxabenzo[1,2;4,5]dicyclohepten-6-yl)acrylic acid tert-butyl ester
  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

• Palladium-Catalyzed Alkylation-Alkenylation Reactions: Rapid Access to Tricyclic Mescaline Analogues
  作者：Mark Lautens、Dino Alberico

  DOI：10.1055/s-2006-941583

  日期：2006.11

  heterocycles were synthesized in good yields from a Heck acceptor and an aryl iodide containing two tethered alkyl bromides. This methodology was applied to the synthesis of a tricyclic mescaline analogue.

  描述了一种降冰片烯介导的钯催化序列，其中在一个锅中形成两个烷基-芳基键和一个烯基-芳基键。从 Heck 受体和含有两个系链烷基溴的芳基碘化物以良好的产率合成了各种对称和不对称的三环杂环。该方法被应用于合成三环甲司卡林类似物。
• 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.