N-(2,6-dimethylphenyl)imidazole[1,2-a]pyridin-3-amine | 823806-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-(2,6-dimethylphenyl)imidazole[1,2-a]pyridin-3-amine
• 英文别名: N-(2,6-dimethylphenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 823806-51-5
• 化学式: C₁₅H₁₅N₃
• 分子量: 237.304
• InChiKey: BFHYVWBDMUQOOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 2,6-二甲基苯基异腈 、 乙醛酸 在 macroporous polystyrene carbonate resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 以71%的产率得到N-(2,6-dimethylphenyl)imidazole[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Glyoxylic Acid and MP-Glyoxylate:  Efficient Formaldehyde Equivalents in the 3-CC of 2-Aminoazines, Aldehydes, and Isonitriles

  摘要：

  Glyoxylic acid, either in solution or immobilized on MP-carbonate (MP-glyoxylate), participates in an uncatalyzed 3-CC with 2-aminoazines and isonitriles to afford novel 2-unsubstituted-3-amino-imidazoheterocycles. MP-glyoxylate serves as a particularly efficient and experimentally convenient formaldehyde equivalent and readily liberates products through decarboxylation/self-release from the resin. These examples furthermore constitute the first application in which MP-CO3 serves as a solid support for transformations involving carboxylic acids.

  DOI：

  10.1021/ol0478234

文献信息

• 3-AMINOIMIDAZO [1,2-A] PYRIDINE DERIVATIVES AS SGLT INHIBITORS
  申请人：MEDERSKI Werner

  公开号：US20110195991A1

  公开（公告）日：2011-08-11

  Novel compounds of the formula I, in which X, Y, R, R′, R 1 , R 1′ , R 1″ , R 2 , R 2′ , R 2″ , R 3 , R 3′ , R 4 , R 4′ and n have the meanings indicated in Patent Claim 1 , are suitable as antidiabetics

  化合物的新颖结构如公式I所示，其中X、Y、R、R′、R1、R1′、R1″、R2、R2′、R2″、R3、R3′、R4、R4′和n的含义如专利权利要求书中所示，适用于抗糖尿病药物。
• A Regioselective and High-Yielding Method for Formaldehyde Inclusion in the 3CC Groebke-Blackburn-Bienaymé Reaction: One-Step Access to 3-Aminoimidazoazines
  作者：Hong-yu Li、Anuj Sharma

  DOI：10.1055/s-0030-1260568

  日期：2011.6

  A regioselective, mild, convenient, and effective condition is developed for the inclusion of glyoxylic acid as formaldehyde equivalent in the 3CC reaction towards synthesis of 3-aminoalkyl imidazo-azines. In general, formaldehydes do not perform well with Ugi-type multicomponent sequences, and the method reported here is a regioselective and high-yielding one for the HCHO variant of Groebke-Blackburn-Bienaymé reaction.

  开发了一种区域选择性、温和、方便且有效的条件，用于在3CC反应中将乙醛酸作为甲醛等效物纳入，以合成3-氨基烷基咪唑类杂环化合物。一般而言，甲醛在Ugi型多组分反应中表现不佳，而此处报道的方法则是一种区域选择性高且产率高的Groebke-Blackburn-Bienaymé反应的HCHO变体。
• US8258151B2
  申请人：——

  公开号：US8258151B2

  公开（公告）日：2012-09-04
• Glyoxylic Acid and MP-Glyoxylate:  Efficient Formaldehyde Equivalents in the 3-CC of 2-Aminoazines, Aldehydes, and Isonitriles
  作者：Michael A. Lyon、Timothy S. Kercher

  DOI：10.1021/ol0478234

  日期：2004.12.1

  Glyoxylic acid, either in solution or immobilized on MP-carbonate (MP-glyoxylate), participates in an uncatalyzed 3-CC with 2-aminoazines and isonitriles to afford novel 2-unsubstituted-3-amino-imidazoheterocycles. MP-glyoxylate serves as a particularly efficient and experimentally convenient formaldehyde equivalent and readily liberates products through decarboxylation/self-release from the resin. These examples furthermore constitute the first application in which MP-CO3 serves as a solid support for transformations involving carboxylic acids.