Butyl-(2-phenyl-imidazo[1,2-a]pyrazin-3-yl)-amine | 438185-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Butyl-(2-phenyl-imidazo[1,2-a]pyrazin-3-yl)-amine
• 英文别名: N-butyl-2-phenylimidazo[1,2-a]pyrazin-3-amine
• CAS: 438185-92-3
• 化学式: C₁₆H₁₈N₄
• 分子量: 266.346
• InChiKey: KQIKQQVGQVPDIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴氯苯 、 Butyl-(2-phenyl-imidazo[1,2-a]pyrazin-3-yl)-amine 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以53%的产率得到N-(n-butyl)-6-(4-chlorophenyl)-2-phenylimidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  C–H Bond Functionalization Under Metalation–Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-a]pyrazine

  摘要：

  Concerted metalation deprotonation (CMD) approach with appropriate proton shuttle precursor, base, and solvent (PivOH-K2CO3-toluene) has rendered a regioselective Pd-catalyzed C6-arylation of 3-aminoimidazo[1,2-a]pyrazine, a therapeutically relevant scaffold accessible by multicomponent reaction. The arylation of this heteroarene suffers from competing C5 and C2'-arylation reactions, while the developed process has virtually eliminated these competing arylations. Density functional calculations for CMD C-H activation at C6, C5, C8, and C2' sites imply that the energy barrier with distortion energy penalty as major contributing component influences the regioselectivity.

  DOI：

  10.1021/jo301065s
• 作为产物：
  描述：

  氨基吡嗪 、 异腈基正丁烷 、 苯甲醛 在 cation exchange resin 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 Butyl-(2-phenyl-imidazo[1,2-a]pyrazin-3-yl)-amine
  参考文献：
  名称：

  新的三组分缩合反应并行合成3-氨基咪唑并[1,2-a]吡啶和吡嗪

  摘要：

  三氟甲磺酸scan催化2-氨基吡啶，醛和异腈之间的三组分缩合反应，得到3-氨基咪唑并[1,2-a]吡啶的衍生物。氨基吡嗪反应类似。通过在离子交换树脂上平行合成和纯化以高收率制备的杂环库在氨基上进行进一步反应。

  DOI：

  10.1016/s0040-4039(98)00653-4

文献信息

• [DE] SUBSTANZBIBLIOTHEK ENTHALTEND BICYCLISCHE IMIDAZO-5-YL-AMINE UND/ODER BICYCLISCHE IMIDAZO-3-YL-AMINE<br/>[EN] SUBSTANCE LIBRARY CONTAINING BICYCLIC IMIDAZO-5-YL-AMINES AND/OR BICYCLIC IMIDAZO-3-YL-AMINES<br/>[FR] BIBLIOTHEQUE DE SUBSTANCES CONTENANT DES IMIDAZO-5-YL-AMINES BICYCIQUES ET/OU DES IMIDAZO-3-YL-AMINES BICYCLIQUES
  申请人：GRUENENTHAL GMBH

  公开号：WO2001027119A2

  公开（公告）日：2001-04-19

  Substanzbibliothek enthaltend bicyclische Imidazo-5-yl-amine und/oder bicyclische Imidazo-3-yl-amine der allgemeinen Formeln (I) bzw. (II), ein Verfahren zur Herstellung dieser Substanzbibliothek sowie die Verwendung von Substanzen aus dieser Substanzbibliothek zur Herstellung eines Arzneimittels zur Behandlung von Schmerz.
• Parallel synthesis of 3-aminoimidazo[1,2-a]pyridines and pyrazines by a new three-component condensation
  作者：Christopher Blackburn、Bing Guan、Paul Fleming、Kazumi Shiosaki、Shirling Tsai

  DOI：10.1016/s0040-4039(98)00653-4

  日期：1998.5

  A three-component condensation reaction between 2-aminopyridine, an aldehyde and an isonitrile catalyzed by scandium triflate affords derivatives of 3-aminoimidazo[1,2-a]pyridine; aminopyrazine reacts similarly. A library of heterocycles, prepared in high yield by parallel synthesis and purification on an ion-exchange resin, was subjected to further reactions at the amino group.

  三氟甲磺酸scan催化2-氨基吡啶，醛和异腈之间的三组分缩合反应，得到3-氨基咪唑并[1,2-a]吡啶的衍生物。氨基吡嗪反应类似。通过在离子交换树脂上平行合成和纯化以高收率制备的杂环库在氨基上进行进一步反应。
• C–H Bond Functionalization Under Metalation–Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-<i>a</i>]pyrazine
  作者：Sankar K. Guchhait、Somnath Kandekar、Maneesh Kashyap、Nikhil Taxak、Prasad V. Bharatam

  DOI：10.1021/jo301065s

  日期：2012.9.21

  Concerted metalation deprotonation (CMD) approach with appropriate proton shuttle precursor, base, and solvent (PivOH-K2CO3-toluene) has rendered a regioselective Pd-catalyzed C6-arylation of 3-aminoimidazo[1,2-a]pyrazine, a therapeutically relevant scaffold accessible by multicomponent reaction. The arylation of this heteroarene suffers from competing C5 and C2'-arylation reactions, while the developed process has virtually eliminated these competing arylations. Density functional calculations for CMD C-H activation at C6, C5, C8, and C2' sites imply that the energy barrier with distortion energy penalty as major contributing component influences the regioselectivity.