3-(2-bromoethoxy)-5-iodophenol | 916905-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(2-bromoethoxy)-5-iodophenol
• 英文别名: 3-(2-Bromoethoxy)-5-iodophenol
• CAS: 916905-35-6
• 化学式: C₈H₈BrIO₂
• 分子量: 342.959
• InChiKey: SBCNZKFYBRXALF-UHFFFAOYSA-N

物化性质

• 熔点：
  139-141 °C
• 沸点：
  414.1±40.0 °C(Predicted)
• 密度：
  2.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethoxy)-5-iodophenol 在 palladium diacetate 降冰片烯 、 potassium carbonate 、 caesium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 丙酮 为溶剂， 反应 36.17h， 生成 tert-butyl (2E)-3-(2,3,6,7-tetrahydro-5H-furo[3,2-g]chromen-4-yl)acrylate
  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
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 氢碘酸 、 碘 、 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 、 正戊烷 为溶剂， 反应 48.0h， 生成 3-(2-bromoethoxy)-5-iodophenol
  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 Polycyclic Benzonitriles via a One-Pot Aryl Alkylation/Cyanation Reaction
  作者：Brian Mariampillai、Dino Alberico、Valérie Bidau、Mark Lautens

  DOI：10.1021/ja064742p

  日期：2006.11.1

  A norbornene-mediated palladium-catalyzed tandem alkylation/cyanation sequence is described in which an alkyl-aryl bond and a nitrile-aryl bond are formed in one pot. A variety of sterically hindered, five-, six-, and seven-membered ring benzonitriles were synthesized in good yields from easily accessible starting materials.

  描述了降冰片烯介导的钯催化串联烷基化/氰化序列，其中在一个锅中形成烷基-芳基键和腈-芳基键。各种空间位阻、五元、六元和七元环苯甲腈从容易获得的起始材料中以良好的产率合成。
• 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.