(Z)-2-butyl-4-(dimethylaminomethylene)-2-imidazolin-5-one | 168900-00-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-butyl-4-(dimethylaminomethylene)-2-imidazolin-5-one
• 英文别名: (4Z)-2-butyl-4-(dimethylaminomethylidene)-1H-imidazol-5-one
• CAS: 168900-00-3
• 化学式: C₁₀H₁₇N₃O
• 分子量: 195.264
• InChiKey: PLIWOXYHWDLZPN-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-butyl-4-(dimethylaminomethylene)-2-imidazolin-5-one 在 三氯氧磷 作用下， 反应 1.5h， 以88%的产率得到咪唑醛
  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
• 作为产物：
  描述：

  戊腈 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 二丁醚 、 甲苯 为溶剂， 反应 147.0h， 生成 (Z)-2-butyl-4-(dimethylaminomethylene)-2-imidazolin-5-one
  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

• Verfahren zur Herstellung von 2-substituierten 5-Chlorimidazol-4-carbaldehyden
  申请人：LONZA AG

  公开号：EP0653422A1

  公开（公告）日：1995-05-17

  Es wird ein neues Verfahren zur Herstellung von 2-subst. 5-Chlorimidazol-4-carbaldehyden der allgemeinen Formel beschrieben. Dabei wird ein Glycinesterhydrohalogenid mit einem Imidsäureester zu einem 2-subst. 3,5-Dihydroimidazol-4-on ringgeschlossen, mit einem N,N-subst. Formamidacetal in das N,N-subst. Aminomethylenimidazolinon überführt und schliesslich chloriert. Die 5-Chlorimidazol-4-carbaldehyde sind wichtige Zwischenprodukte in der Herstellung von blutdrucksenkenden Pharmazeutika.

  制备通式为 2-取代基-5-氯咪唑-4-羧醛的新工艺通式为 5-氯咪唑-4-甲醛的新工艺 的新工艺。在这一工艺中，甘氨酸酯氢卤化物与咪唑酸酯环状闭合，形成 2-亚甲基-3,5-二氢咪唑-4-酮，并带有一个 N-叔丁氧羰基。3,5-二氢咪唑-4-酮，并将 N,N-亚甲基甲酰胺缩醛转化为 N,N-亚甲基甲酰胺。甲酰胺缩醛转化为 N,N-亚甲基咪唑酰胺。氨基亚甲基咪唑啉酮，最后氯化。 5-chloroimidazole-4-carbaldehydes 是生产抗高血压药物的重要中间体。
• US5486617A
  申请人：——

  公开号：US5486617A

  公开（公告）日：1996-01-23
• US5536841A
  申请人：——

  公开号：US5536841A

  公开（公告）日：1996-07-16
• 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.