(4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-acetonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-acetonitrile
• 英文别名: (4-Methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isochinolin-5-yl)-phenyl-acetonitril；(4-Methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)(phenyl)acetonitrile；2-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-phenylacetonitrile
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: ZFNRSRSOZRYKBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-二甲基巴比妥酸 、 (4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-acetonitrile 在 异丁酰胺 、 三乙胺 作用下， 反应 0.33h， 以35%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：

  摘要：

  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.

  DOI：

  10.1023/a:1020983527851
• 作为产物：
  描述：

  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- 、 苯乙腈 在 甲醇 作用下， 生成 (4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-phenyl-acetonitrile
  参考文献：
  名称：

  XLIV.—异喹啉生物碱类的合成实验。第三部分 脱水cotarnineine苯乙酮等的组成，以及cotarnine的一些新缩合产物的描述

  摘要：

  DOI：

  10.1039/ct9130300361

文献信息

• Freund, Chemische Berichte, 1904, vol. 37, p. 3334
  作者：Freund

  DOI：——

  日期：——
• ——
  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.
• XLIV.—Synthetical experiments in the group of the isoquinoline alkaloids. Part III. The constitution of anhydrocotarnineacetophenone, etc., together with an account of some new condensation products of cotarnine
  作者：Edward Hope、Robert Robinson

  DOI：10.1039/ct9130300361

  日期：——