1-(2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)ethan-1-one | 16858-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)ethan-1-one
• 英文别名: 3-Acetyl-2-methyl-6,7-dihydro-5H-cyclopentapyridin；1-(2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)ethanone
• CAS: 16858-05-2
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: RDWCIIZAUGTFPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 cyclopentanone O-ethanoyloxime 、 乙酰丙酮 在 lithium carbonate 、 copper(I) bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以62%的产率得到1-(2-methyl-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)ethan-1-one
  参考文献：
  名称：

  Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines

  摘要：

  A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.

  DOI：

  10.1021/acs.joc.5b01621

文献信息

• Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines
  作者：Huanfeng Jiang、Jidan Yang、Xiaodong Tang、Jianxiao Li、Wanqing Wu

  DOI：10.1021/acs.joc.5b01621

  日期：2015.9.4

  A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.