3-benzyl-9-phenyl-5H-triazolo[4,5-c]quinolin-4-one | 1353714-69-8

• 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: 3-benzyl-9-phenyl-5H-triazolo[4,5-c]quinolin-4-one
• CAS: 1353714-69-8
• 化学式: C₂₂H₁₆N₄O
• 分子量: 352.395
• InChiKey: JLPRYRFMHIKPRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  o-Nitro-6-chlor-phenyl-propiolsaeure-methylester 在 XPhos 、 2-甲基四氢呋喃 、 palladium diacetate 、 caesium carbonate 、 溶剂黄146 、 锌 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 3-benzyl-9-phenyl-5H-triazolo[4,5-c]quinolin-4-one
  参考文献：
  名称：

  Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes

  摘要：

  Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the regioselectivity of these cycloadditions. Several new substrates were predicted that would either give enhanced regiocontrol or invert the regiochemical preference. Experimentally, the alkynes were screened in the [3 + 2] cycloaddition with benzyl azide. Of the 11 alkynes screened experimentally, the acetylenes containing halogen substitution directly on the alkyne provided the highest levels of regioselectivity. These haloalkynes were also shown to tolerate variation of the azide moiety with continued good levels of regioselectivity in most cases. Diverse functional groups can be incorporated through the cycloaddition process and their subsequent orthogonal modification was demonstrated.

  DOI：

  10.1021/jo202467k

文献信息

• Synthesis and Computational Analysis of Densely Functionalized Triazoles Using <i>o</i>-Nitrophenylalkynes
  作者：Melissa L. McIntosh、Ryne C. Johnston、Ommidala Pattawong、Bradley O. Ashburn、Michael R. Naffziger、Paul Ha-Yeon Cheong、Rich G. Carter

  DOI：10.1021/jo202467k

  日期：2012.1.20

  Dipolar cylcoadditions with azides using a series of o-nitrophenylethynes and disubstituted alkynes were studied experimentally and computationally. Density functional theory computations reveal the steric and electronic parameters that control the regioselectivity of these cycloadditions. Several new substrates were predicted that would either give enhanced regiocontrol or invert the regiochemical preference. Experimentally, the alkynes were screened in the [3 + 2] cycloaddition with benzyl azide. Of the 11 alkynes screened experimentally, the acetylenes containing halogen substitution directly on the alkyne provided the highest levels of regioselectivity. These haloalkynes were also shown to tolerate variation of the azide moiety with continued good levels of regioselectivity in most cases. Diverse functional groups can be incorporated through the cycloaddition process and their subsequent orthogonal modification was demonstrated.