5-chloro-2-(2-chlorobutyl)imidazole-4-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloro-2-(2-chlorobutyl)imidazole-4-carbaldehyde
• 英文别名: 5-chloro-2-(2-chlorobutyl)-1H-imidazole-4-carbaldehyde
• 化学式: C₈H₁₀Cl₂N₂O
• 分子量: 221.086
• InChiKey: PLLHTRLASLTUFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-戊烯腈 在 盐酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二丁醚 、 甲苯 为溶剂， 反应 9.0h， 生成 5-chloro-2-(2-chlorobutyl)imidazole-4-carbaldehyde
  参考文献：
  名称：

  Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde:  A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan

  摘要：

  Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl3/DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl3/DMF allowed development of several closely related syntheses of aldehyde 2.

  DOI：

  10.1021/jo9824910

文献信息

• Novel Syntheses of 2-Butyl-5-chloro-3<i>H</i>-imidazole-4-carbaldehyde:  A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan
  作者：Gareth J. Griffiths、Michael B. Hauck、René Imwinkelried、Jörg Kohr、Conrad A. Roten、Gerhard C. Stucky、Jacques Gosteli

  DOI：10.1021/jo9824910

  日期：1999.10.1

  Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl3/DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl3/DMF allowed development of several closely related syntheses of aldehyde 2.