methyl 3-(MIDA boronate)-1-oxo-1,2-dihydroisoquinoline-6-carboxylate | 1414351-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: methyl 3-(MIDA boronate)-1-oxo-1,2-dihydroisoquinoline-6-carboxylate
• 英文别名: 6-Carboxymethyl-1,2-dihydro-1-oxoisoquinoline-3-MIDA boronate；methyl 3-(5-methyl-3,7-dioxo-2,8-dioxa-5-azonia-1-boranuidabicyclo[3.3.0]octan-1-yl)-1-oxo-2H-isoquinoline-6-carboxylate
• CAS: 1414351-04-4
• 化学式: C₁₆H₁₅BN₂O₇
• 分子量: 358.115
• InChiKey: KSWYHXOJOYFZMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.98
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethynyl MIDA boronate 、 methyl 4-((pivaloyloxy)carbamoyl)benzoate 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 cesium pivalate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以92%的产率得到methyl 3-(MIDA boronate)-1-oxo-1,2-dihydroisoquinoline-6-carboxylate
  参考文献：
  名称：

  Mild Rh(III)-Catalyzed C–H Activation and Annulation with Alkyne MIDA Boronates: Short, Efficient Synthesis of Heterocyclic Boronic Acid Derivatives

  摘要：

  Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.

  DOI：

  10.1021/ja310153v