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9,10-diethoxy-6,7-dihydro-4-imino-2-(thiophen-2-yl)-4H-benzo[a]quinolizine-3-carbonitrile

中文名称
——
中文别名
——
英文名称
9,10-diethoxy-6,7-dihydro-4-imino-2-(thiophen-2-yl)-4H-benzo[a]quinolizine-3-carbonitrile
英文别名
9,10-Diethoxy-4-imino-2-thiophen-2-yl-6,7-dihydrobenzo[a]quinolizine-3-carbonitrile
9,10-diethoxy-6,7-dihydro-4-imino-2-(thiophen-2-yl)-4H-benzo[a]quinolizine-3-carbonitrile化学式
CAS
——
化学式
C22H21N3O2S
mdl
——
分子量
391.494
InChiKey
ADQBUDGQYWHUCT-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.6
  • 重原子数:
    28
  • 可旋转键数:
    5
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.27
  • 拓扑面积:
    97.6
  • 氢给体数:
    1
  • 氢受体数:
    5

反应信息

  • 作为产物:
    描述:
    1-甲基-6,7-二乙氧基-3,4-二氢异喹啉(2-噻吩亚甲基)甲烷-1,1-二甲腈哌啶 作用下, 以 乙腈 为溶剂, 反应 3.0h, 以82%的产率得到9,10-diethoxy-6,7-dihydro-4-imino-2-(thiophen-2-yl)-4H-benzo[a]quinolizine-3-carbonitrile
    参考文献:
    名称:
    New Routes to Fused Isoquinolines
    摘要:
    Treatment of 6.7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides, 10 in the presence of Et3N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4-triazolo[3,4-a]isoquinolines 11 and 13. respectively, in high yield (Schemes 2 and 3.). The products are formed via regioselective 1,3-dipolar cycloaddition of the intermediate nitrilimines 9 with the isoquinoline C=N bond. Reaction of 6,7-diethoxy-3,4-dihydroisoquinoline-1-acetonitrile (4a) with ethyl alpha-cyanocinnamates 15 in the presence of piperidine m refluxing MeCN yielded benzo[a]quinolizin-4-ones 16 (Scheme 4), Under the same conditions. 12 and arylidene malononitriles 19 reacted to give benzo[a]quinolizin-4-imines 20 (Scheme5). Instead of 15 and 19, mixtures of an aromatic aldehyde. and ethyl cyanoacetate or malononitrile. respectively can be used in a one-pot reaction.
    DOI:
    10.1002/1522-2675(200201)85:1<320::aid-hlca320>3.0.co;2-x
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文献信息

  • New Routes to Fused Isoquinolines
    作者:Enas M. Awad、Nehal M. Elwan、Hamdi M. Hassaneen、Anthony Linden、Heinz Heimgartner
    DOI:10.1002/1522-2675(200201)85:1<320::aid-hlca320>3.0.co;2-x
    日期:2002.1
    Treatment of 6.7-diethoxy-3,4-dihydroisoquinoline (8) and its 1-methyl derivative 12 with hydrazonoyl halides, 10 in the presence of Et3N in THF under reflux afforded the corresponding 5,6-dihydro-1,2,4-triazolo[3,4-a]isoquinolines 11 and 13. respectively, in high yield (Schemes 2 and 3.). The products are formed via regioselective 1,3-dipolar cycloaddition of the intermediate nitrilimines 9 with the isoquinoline C=N bond. Reaction of 6,7-diethoxy-3,4-dihydroisoquinoline-1-acetonitrile (4a) with ethyl alpha-cyanocinnamates 15 in the presence of piperidine m refluxing MeCN yielded benzo[a]quinolizin-4-ones 16 (Scheme 4), Under the same conditions. 12 and arylidene malononitriles 19 reacted to give benzo[a]quinolizin-4-imines 20 (Scheme5). Instead of 15 and 19, mixtures of an aromatic aldehyde. and ethyl cyanoacetate or malononitrile. respectively can be used in a one-pot reaction.
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