2-bromo-N-((2-cyanoquinolin-3-yl)methyl)cyclohex-1-enecarboxamide | 1166376-03-9

• 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: 2-bromo-N-((2-cyanoquinolin-3-yl)methyl)cyclohex-1-enecarboxamide
• 英文别名: 2-bromo-N-[(2-cyanoquinolin-3-yl)methyl]cyclohexene-1-carboxamide
• CAS: 1166376-03-9
• 化学式: C₁₈H₁₆BrN₃O
• 分子量: 370.249
• InChiKey: AZSGPSBVFCOVDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-((2-cyanoquinolin-3-yl)methyl)cyclohex-1-enecarboxamide 在 1,1'-双(二苯基膦)二茂铁 、 potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 7,8,9,10-tetrahydroluotonin A
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives

  摘要：

  With the catalysis of palladium, a number of 2-bromo-N-(2-iodobenzyl)benzamides underwent sequential cyanation/N-addition/N-arylation leading to the efficient construction of isoindolo[1,2-b]quinazolin-10(12H)-ones in a two-stage, one-pot manner. This method also allowed the convenient synthesis of luotonin A and its derivatives.

  DOI：

  10.1021/ol901305q
• 作为产物：
  描述：

  potassium cyanide 、 2-bromo-N-((2-bromoquinolin-3-yl)methyl)cyclohex-1-enecarboxamide 在 palladium diacetate 、 双(2-二苯基磷苯基)醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 2-bromo-N-((2-cyanoquinolin-3-yl)methyl)cyclohex-1-enecarboxamide
  参考文献：
  名称：

  Palladium-Catalyzed Sequential Cyanation/N-Addition/N-Arylation in One-Pot: Efficient Synthesis of Luotonin A and Its Derivatives

  摘要：

  With the catalysis of palladium, a number of 2-bromo-N-(2-iodobenzyl)benzamides underwent sequential cyanation/N-addition/N-arylation leading to the efficient construction of isoindolo[1,2-b]quinazolin-10(12H)-ones in a two-stage, one-pot manner. This method also allowed the convenient synthesis of luotonin A and its derivatives.

  DOI：

  10.1021/ol901305q

文献信息

• Intramolecular Formal [4 + 2] Cycloaddition of Nitriles with Amides Triggered by TMSOTf/Et₃N: Highly Efficient Construction of Pyrrolo[1,2-<i>a</i>]pyrimidin-4(6<i>H</i>)-ones
  作者：Feng Liu、Chaozhong Li

  DOI：10.1021/jo900907h

  日期：2009.8.7

  By treatment with TMSOTf/Et3N, N-(2-cyanoarylmethyl)-substituted acrylamides or beta-ketoamides underwent N-addition cascades under mild conditions to afford the corresponding pyrrolo[1,2-a]pyrimidin-4(6H)-ones as the formal [4 + 2] cycloaddition products in high yields.