3-甲氧基-2-(3,4,5-三甲氧基苄基)丙腈 | 30078-01-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-甲氧基-2-(3,4,5-三甲氧基苄基)丙腈
• 英文名称: 3-Methoxy-2-<3.4.5-trimethoxy-benzyl>-acrylnitril
• 英文别名: 3-methoxy-2-(3,4,5-trimethoxybenzyl)propiononitrile；3-Methoxy-2-[(3,4,5-trimethoxyphenyl)methyl]prop-2-enenitrile
• CAS: 30078-01-4
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: QJTWJBLWEVAMDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2926909090

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 3-甲氧基-2-(3,4,5-三甲氧基苄基)丙腈
  参考文献：
  名称：

  Syntheses of antibacterial 2,4-diamino-5-benzylpyrimidines. Ormetoprim and trimethoprim

  摘要：

  A general and mild method for the synthesis of 2,4-diamino-5-benzylpyrimidines was achieved by the Friedel-Crafts reaction between 2-(methoxymethylene)-3-methoxypropanenitrile (10) and an activated aromatic substrate followed by treatment with guanidine. The method is illustrated by a synthesis of ormetoprim (2) in 75% overall yield from 3,4-dimethoxytoluene (12). Efficient syntheses of trimethoprim (1) and 2 were also accomplished via prior base-catalyzed 1,3-prototropic isomerization of cinnamonitriles 19 and 20, respectively, followed by condensation with guanidine. 12 was prepared from 3-bromo-4-methoxytoluene by a Cu(I)-catalyzed displacement of bromine by methoxide and 4,5-dimethoxy-2-methylbenzaldehyde was obtained from 12 in 87% yield by a pyridine-catalyzed Vilsmeier reaction using DMF-POCl3.

  DOI：

  10.1021/jo00039a006