dimethyl 2-(2-(5-chloro-7-iodoquinolin-8-yloxymethyl)allyl)-2-(2-methylallyl)malonate | 1333120-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dimethyl 2-(2-(5-chloro-7-iodoquinolin-8-yloxymethyl)allyl)-2-(2-methylallyl)malonate
• 英文别名: Dimethyl 2-[2-[(5-chloro-7-iodoquinolin-8-yl)oxymethyl]prop-2-enyl]-2-(2-methylprop-2-enyl)propanedioate
• CAS: 1333120-20-9
• 化学式: C₂₂H₂₃ClINO₅
• 分子量: 543.786
• InChiKey: REUWDZJRCMBJNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(2-(5-chloro-7-iodoquinolin-8-yloxymethyl)allyl)-2-(2-methylallyl)malonate 在 Pd(Q-Phos)2 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以33 mg的产率得到rac-(1R,5R)-dimethyl 5'-chloro-5-iodomethyl-5-methyl-2'H-spiro[cyclohexane-1,3'-furo[3,2-h]quinoline]-3,3-dicarboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes

  摘要：

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

  DOI：

  10.1021/ja206099t
• 作为产物：
  描述：

  dimethyl (2-methyl-2-propenyl)-propanedioate 在 四丁基溴化铵 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 dimethyl 2-(2-(5-chloro-7-iodoquinolin-8-yloxymethyl)allyl)-2-(2-methylallyl)malonate
  参考文献：
  名称：

  Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes

  摘要：

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

  DOI：

  10.1021/ja206099t