5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1,3-dimethylbarbituric acid | 464171-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1,3-dimethylbarbituric acid
• 英文别名: 5-(8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinolin-1-yl)-1,3-dimethylbarbituric acid；(5-dihydrocotarnyl-1,3-dimethylbarbituric acid；5-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 464171-44-6
• 化学式: C₁₈H₂₁N₃O₆
• 分子量: 375.381
• InChiKey: SJZDFFWKIVZPDL-UHFFFAOYSA-N

物化性质

• 沸点：
  489.7±55.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-二甲基巴比妥酸 、 5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1,3-dimethylbarbituric acid 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以47%的产率得到4'-methoxy-1,3-dimethyl-7'-(1,3-dimethyl-2,4,6-trioxoperhydropyrimidin-5-yl)-2,4,6-trioxospiro[perhydropyrimidine-5,6'-(5',6',7',8'-tetrahydro[1,3]dioxolo[4,5-g]naphthalene)]
  参考文献：
  名称：

  Chemical modification of plant alkaloids. 5. Spirocyclic systems based on cotarnine and barbituric acids

  摘要：

  Cotarnine与巴比妥酸及其N-烷基巴比妥酸和1,3-二甲基-2-硫代类似物在强迫条件下反应，以产生螺旋环系统。在第一步中形成了加成物，进一步转化包括骨架重排（一种T反应）及随后的脱氨反应。N-甲基cotarnine与1,3-二甲基巴比妥酸的反应类似。对螺旋环产物的性质进行了研究。它们在CH酸和芳香部位上进行了进一步修饰。

  DOI：

  10.1007/s10600-008-0013-0
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 1,3-二氧杂环戊烯并[4,5-g]异喹啉-5-醇,5,6,7,8-四氢-4-甲氧基-6-甲基- 以 氯仿 为溶剂， 反应 0.03h， 以86%的产率得到5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1,3-dimethylbarbituric acid
  参考文献：
  名称：

  摘要：

  The reaction of barbituric acid and its N-substituted derivatives and 2-thio analogs with cotarnine forms 5-(4-methoxy-6-methyl-5,6,7,8-tetrahildro-2H-1,3-methylenedioxy-[4,5-g]isoquinolinyl-1)barbituric acids, a new class of zwitter-ions, the structure of which was studied by H-1 and C-13 NMR spectroscopy and mass spectrometry. The prepared compounds exist in solution as stable intermolecular associates and have a complicated H-bonded structure.

  DOI：

  10.1023/a:1014821016904

文献信息

• ——
  作者：K. A. Krasnov、V. G. Kartsev、V. N. Khrustalev

  DOI：10.1023/a:1020983527851

  日期：——

  6-Methyl-4-methoxy-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol (cotarnine) and its derivatives, namely, 5-dihydrocotamyl-1,3-dimethylbarbituric acid, dihydro-cotarnylnitromethane, and dihydrocotarnylphenylacetonitrile, react with an excess of 1,3-dimethylbarbituric acid to give its 5,5-spiro derivative. The structure of the latter was proved by X-ray diffraction analysis A possible reaction mechanism was discussed.
• Krasnov; Kartsev; Khrustalev, Russian Chemical Bulletin, 2003, vol. 52, # 3, p. 705 - 709
  作者：Krasnov、Kartsev、Khrustalev

  DOI：——

  日期：——