3-cyclohexyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[4,3-a]isoquinoline-1-carbonitrile | 51054-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 3-cyclohexyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[4,3-a]isoquinoline-1-carbonitrile
• 英文别名: 3-cyclohexyl-9,10-dimethoxy-3,4,6,7-tetrahydro-pyrimido[6,1-a]isoquinoline-1-carbonitrile；3-cyclohexyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinoline-1-carbonitrile；3-cyclohexyl-9,10-dimethoxy-2,4,6,7-tetrahydropyrimido[6,1-a]isoquinoline-1-carbonitrile
• CAS: 51054-44-5
• 化学式: C₂₁H₂₇N₃O₂
• 分子量: 353.464
• InChiKey: CDFXHDABQJDUAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)acetonitrile 、 环己胺 以 乙醇 为溶剂， 反应 0.17h， 以65%的产率得到3-cyclohexyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[4,3-a]isoquinoline-1-carbonitrile
  参考文献：
  名称：

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions

  摘要：

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and beta-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides.

  DOI：

  10.1134/s1070428011050137

文献信息

• 6,7-Dimethoxy-3,4-dihydroisoquinolin-1(2H)-ylidenoacetonitrile in some fusion reactions
  作者：A. A. Afon’kin、M. L. Kostrikin、A. E. Shumeiko、A. F. Popov

  DOI：10.1134/s1070428011050137

  日期：2011.5

  6,7-Dimethoxy-3,4-dihydroisoquinolin-1-ylacetonitrile in the enamine form readily reacts with acyl iso(thio)cyanates affording in high yields 1,2-fused oxo- and thioxodihydropyrimidoisoquinolines and thiouracyloisoquinolines. The reaction of the enamine with primary amines of diverse classes in the presence of 2 equiv of formaldehyde resulted in 1,2-fused N-substituted tetrahydropyrimidinoisoquinolines whose yields depended on the basicity and sterical accessibility of the reagent. Fused 5-hydroxyindolo-, dioxopyrrolo-, pyrroloisoquinolines formed in medium yields in the one-stage reactions of the enamine with p-benzoquinone, oxalyl chloride, and beta-nitrostyrene respectively. The reaction of 1-cyanomethyl-6,7-dimethoxydihydroisoquinoline with acrylonitrile leads to the formation of 1,2-fused iminopyridinoisoquinoline easily hydrolysable to pyridine derivative and readily reacting by the amidine group with aroyl chlorides and arylsulfonyl chlorides.