(E)-n-butyl 2-(6-benzyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ylidene)acetate | 1610422-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (E)-n-butyl 2-(6-benzyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ylidene)acetate
• 英文别名: (E)-butyl 2-(6-benzyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ylidene)acetate；butyl (2E)-2-(6-benzyl-7-oxopyrrolo[3,4-b]pyridin-5-ylidene)acetate
• CAS: 1610422-31-5
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: AWHNZYBIGJELCC-GHRIWEEISA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  540.3±50.0 °C(predicted)
• 密度：
  1.272±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-吡啶甲酰氯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 29.0h， 生成 (E)-n-butyl 2-(6-benzyl-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ylidene)acetate
  参考文献：
  名称：

  Rh(III)-Catalyzed Cascade Oxidative Olefination/Cyclization of Picolinamides and Alkenes via C–H Activation

  摘要：

  Rh(III)-catalyzed cascade oxidative alkenylation/cyclization of picolinamides and alkenes to furnish pyrido pyrrolone derivatives is described, in which three C-H bonds and one N-H bond broke, while one C-C bond and one C-N bond formed. The reaction proceeded with high yield and high regioselectivity and stereoselectivity. Moreover, copper acetate can also be used in catalytic amounts with O-2 serving as the terminal oxidant.

  DOI：

  10.1021/ol501275r

文献信息

• Synthesis of alkylidene pyrrolo[3,4-b]pyridin-7-one derivatives via Rh^III-catalyzed cascade oxidative alkenylation/annulation of picolinamides
  作者：Ángel Manu Martínez、Nuria Rodríguez、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1039/c4cc02322f

  日期：——

  A practical Rh-catalyzed oxidative cascade ortho-olefination/annulation of picolinamides leading to pyrrolo[3,4-b]pyridines has been developed.

  一种实用的Rh催化氧化级联邻位烯烃化/环化反应已被开发，可将吡啶甲酰胺转化为吡咯并[3,4-b]吡啶。
• Rh(III)-Catalyzed Cascade Oxidative Olefination/Cyclization of Picolinamides and Alkenes via C–H Activation
  作者：Shangjun Cai、Chao Chen、Peng Shao、Chanjuan Xi

  DOI：10.1021/ol501275r

  日期：2014.6.6

  Rh(III)-catalyzed cascade oxidative alkenylation/cyclization of picolinamides and alkenes to furnish pyrido pyrrolone derivatives is described, in which three C-H bonds and one N-H bond broke, while one C-C bond and one C-N bond formed. The reaction proceeded with high yield and high regioselectivity and stereoselectivity. Moreover, copper acetate can also be used in catalytic amounts with O-2 serving as the terminal oxidant.