5,5'-diiodo-2H,2'H-4,4'-bichromene | 1477520-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,5'-diiodo-2H,2'H-4,4'-bichromene
• 英文别名: 3-iodo-4-(3-iodo-2H-chromen-4-yl)-2H-chromene
• CAS: 1477520-20-9
• 化学式: C₁₈H₁₂I₂O₂
• 分子量: 514.101
• InChiKey: SPLPFHTWBYCVLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  5,5'-diiodo-2H,2'H-4,4'-bichromene 、 3-氯苯硼酸 在 palladium diacetate 、 cesium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 12.08h， 以67%的产率得到3,3'-bis(3-chlorophenyl)-2H,2'H-4,4'-bichromene
  参考文献：
  名称：

  ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2H-hydronaphthalene and chromene) and 2H-Quinoline Bearing an Alkenyl Iodide Moiety

  摘要：

  Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.

  DOI：

  10.1021/jo401922b
• 作为产物：
  描述：

  苯基炔丙基醚 在 吡啶 、 四甲基乙二胺 、 氧气 、 一氯化碘 、 copper(l) chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 5,5'-diiodo-2H,2'H-4,4'-bichromene
  参考文献：
  名称：

  ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2H-hydronaphthalene and chromene) and 2H-Quinoline Bearing an Alkenyl Iodide Moiety

  摘要：

  Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.

  DOI：

  10.1021/jo401922b