methyl 1'-methyl-2'-oxo-2',4'-dihydro-1'H,2H-spiro[benzofuran-3,3'-quinoline]-6'-carboxylate | 1384898-02-5

• 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: methyl 1'-methyl-2'-oxo-2',4'-dihydro-1'H,2H-spiro[benzofuran-3,3'-quinoline]-6'-carboxylate
• 英文别名: methyl 1'-methyl-2'-oxospiro[2H-1-benzofuran-3,3'-4H-quinoline]-6'-carboxylate
• CAS: 1384898-02-5
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: VDUWXPLHDRCCCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-((2-iodophenoxy)methyl)acrylic acid 在 草酰氯 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 methyl 1'-methyl-2'-oxo-2',4'-dihydro-1'H,2H-spiro[benzofuran-3,3'-quinoline]-6'-carboxylate
  参考文献：
  名称：

  Spirocyclization by Palladium-Catalyzed Domino Heck–Direct C–H Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones

  摘要：

  Treatment of a DMA solution of anilide 1 with a catalytic amount of palladium acetate (0.025 equiv) and XPhos (0.05 equiv) in the presence of potassium carbonate (2.0 equiv) at 100 degrees C afforded dihydroquinolin-2-ones spiro-fused to dihydrofuranyl, indolinyl, and indanyl 2 in good to excellent yields. The reaction went through a domino sequence involving a 5-exo-trig Heck cyclization followed by an intramolecular direct C-H functionalization.

  DOI：

  10.1021/ol301616w

文献信息

• Spirocyclization by Palladium-Catalyzed Domino Heck–Direct C–H Arylation Reactions: Synthesis of Spirodihydroquinolin-2-ones
  作者：Tiffany Piou、Luc Neuville、Jieping Zhu

  DOI：10.1021/ol301616w

  日期：2012.7.20

  Treatment of a DMA solution of anilide 1 with a catalytic amount of palladium acetate (0.025 equiv) and XPhos (0.05 equiv) in the presence of potassium carbonate (2.0 equiv) at 100 degrees C afforded dihydroquinolin-2-ones spiro-fused to dihydrofuranyl, indolinyl, and indanyl 2 in good to excellent yields. The reaction went through a domino sequence involving a 5-exo-trig Heck cyclization followed by an intramolecular direct C-H functionalization.