1,3-双(2-溴乙氧基)-5-碘苯 | 916905-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1,3-双(2-溴乙氧基)-5-碘苯
• 英文名称: 1,3-bis(2-bromoethoxy)-5-iodobenzene
• CAS: 916905-33-4
• 化学式: C₁₀H₁₁Br₂IO₂
• 分子量: 449.909
• InChiKey: FNMJQKOSJYFQNS-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  453.0±45.0 °C(Predicted)
• 密度：
  2.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-双(2-溴乙氧基)-5-碘苯 在 palladium diacetate 降冰片烯 、 sodium hydroxide 、 乙醇 、 双氧水 、 caesium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 60.0~150.0 ℃ 、550.01 kPa 条件下， 反应 9.11h， 生成 2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran-4-carboxamide
  参考文献：
  名称：

  通过一锅芳基烷基化/氰化反应合成多环苯腈

  摘要：

  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。

  DOI：

  10.1021/ja064742p
• 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 60.0h， 生成 1,3-双(2-溴乙氧基)-5-碘苯
  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

• A Convergent Synthesis of Polysubstituted Aromatic Nitriles via Palladium-Catalyzed C−H Functionalization
  作者：Brian Mariampillai、Julien Alliot、Mengzhou Li、Mark Lautens

  DOI：10.1021/ja075599i

  日期：2007.12.1

  A palladium-catalyzed C-H functionalization reaction for the synthesis of highly substituted aromatic nitriles is reported. The modularity of the reaction is demonstrated by the broad range of aryl iodides which can be coupled with metal cyanides and alkyl halides or aryl bromides.

  报道了一种钯催化的 CH 官能化反应，用于合成高度取代的芳香腈。广泛的芳基碘化物可以与金属氰化物和烷基卤化物或芳基溴化物偶联，证明了该反应的模块化。
• 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。
• Two‐dimensional Supramolecular Polymers Based on Selectively Recognized Aromatic Cation–π and Donor–Acceptor Motifs for Photocatalytic Hydrogen Evolution
  作者：Zhao Gao、Lulu Shi、Fei Yan、Yifei Han、Wei Yuan、Wei Tian

  DOI：10.1002/anie.202302274

  日期：——

  This is the first demonstration of an aromatics-selective recognition strategy for cation-π and donor-acceptor motifs that avoid their mutual interference, thus enabling the construction of two-dimensional supramolecular polymers (2DSPs), which exhibit boosted photocatalytic hydrogen evolution activity.

  这是针对阳离子-π 和供体-受体基序的芳烃选择性识别策略的首次展示，避免了它们的相互干扰，从而实现了二维超分子聚合物 (2DSP) 的构建，其表现出增强的光催化析氢活性。
• 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.
• 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。