2-amino-4-cyano-1-cyclohexylpyrrole | 59661-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-amino-4-cyano-1-cyclohexylpyrrole
• 英文别名: 5-amino-1-cyclohexyl-1H-pyrrole-3-carbonitrile；1-Cyclohexyl-2-amino-4-cyanopyrrol；5-amino-1-cyclohexylpyrrole-3-carbonitrile
• CAS: 59661-26-6
• 化学式: C₁₁H₁₅N₃
• 分子量: 189.26
• InChiKey: RMOGWUVCIGMOAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吲哚-3-乙醛酸甲酯 、 2-amino-4-cyano-1-cyclohexylpyrrole 在 aluminum (III) chloride 作用下， 以 甲醇 为溶剂， 以40%的产率得到1-cyclohexyl-3-cyano-4-oxo-4,5-dihydro-1H-benzo[h]pyrrolo[2,3-c][2,6]naphthyridine
  参考文献：
  名称：

  3-Acylindoles as versatile starting materials for pyridine ring annulation: synthesis of 1-deazapurine isosteres

  摘要：

  The reaction of electron-rich aminoheterocycles with 3-acyl- and 3-formylindoles results in indole ring opening and cyclocondensation to give heteroannulated pyridines, which can be regarded as purine isosteres. The transformations reported herein represent rare examples of domino reactions, which include the cleavage of an indole moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.037
• 作为产物：
  描述：

  (2Z)-2-[(cyclohexylamino)methylidene]butanedinitrile 、 potassium ethoxide 生成 2-amino-4-cyano-1-cyclohexylpyrrole
  参考文献：
  名称：

  BRODRICK A.; WIBBERLEY D. G., J. CHEM. SOC. PERKIN TRANS. PART 1, , 1975, NO 19, 1910-1913

  摘要：

  DOI：

文献信息

• One-Pot, Three-Component Synthesis of 7-Azaindole Derivatives from N-Substituted 2-Amino-4-cyanopyrroles, Various Aldehydes, and Active Methylene Compounds
  作者：Marcelo Vilches-Herrera、Ingo Knepper、Nayane de Souza、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Viktor O. Iaroshenko

  DOI：10.1021/co300042v

  日期：2012.7.9

  practical route to 7-azaindole framework has been developed by one-pot, three-component cyclocondensation of N-substituted 2-amino-4-cyanopyrroles, various aldehydes, and active methylene compounds in ethanol or acetic acid at reflux. Reactions involving tetronic acid, indane-1,3-dione, dimedone, and 5-phenylcyclohexane-1,3-dione gave carbocyclic fused 7-azaindoles, whereas Meldrum’s acid, benzoylacetonitrile

  通过N-取代的2-氨基-4-氰基吡咯，各种醛和活性亚甲基化合物在回流下在乙醇或乙酸中的一锅，三组分环缩合，已经开发出一种有效且实用的通往7-氮杂吲哚骨架的途径。涉及tetronic酸，茚满-1,3-二酮，二酮和5-苯基环己烷-1,3-二酮的反应生成碳环稠合的7-氮杂吲哚，而Meldrum的酸，苯甲酰基乙腈和丙二腈则生成高度取代的7-氮杂吲哚衍生物，使该策略在面向多样性的综合（DOS）中非常有用。
• 3-(Dichloroacetyl)chromone; A New Building Block for the Synthesis of Formylated Purine Isosteres: Design and Synthesis of Fused α-(Formyl)pyridines
  作者：Viktor Iaroshenko、Peter Langer、Satenik Mkrtchyan、Gagik Ghazaryan、Ani Hakobyan、Aneela Maalik、Linda Supe、Alexander Villinger、Andrei Tolmachev、Dmytro Ostrovskyi、Vyacheslav Sosnovskikh、Tariel Ghochikyan

  DOI：10.1055/s-0030-1258364

  日期：2011.2

  The first synthesis of 3-(dichloroacetyl)chromone from 3-(dimethylamino)-1-(2-hydroxyphenyl)propen-1-one and dichloroacetyl chloride is described. The reaction of electron-rich aminoheterocycles with 3-(dichloroacetyl)chromone provides a set of diverse fused pyridines bearing the CHCl2-substituent at the α-position of the pyridine core. Subsequent hydrolysis leads to the formation of annulated α-(formyl)pyridines

  描述了由3-（二甲基氨基）-1-（2-羟基苯基）丙烯-1-酮和二氯乙酰氯首次合成3-（二氯乙酰基）色酮。富电子的氨基杂环与3-（二氯乙酰基）色酮的反应提供了一组不同的稠合吡啶，其在吡啶核的α-位带有CHCl 2-取代基。随后的水解导致环状的α-（甲酰基）吡啶的形成。 3-（二氯乙酰基）色酮-4 H -1-苯并吡喃-4-酮-杂环胺-稠合吡啶-环化反应
• 2,3-Unsubstituted chromones and their enaminone precursors as versatile reagents for the synthesis of fused pyridines
  作者：Viktor O. Iaroshenko、Satenik Mkrtchyan、Ashot Gevorgyan、Mariia Miliutina、Alexander Villinger、Dmytro Volochnyuk、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1039/c1ob06494k

  日期：——

  A divergent and regioselective approach to fused pyridines was developed through formal [3 + 3] cyclocondensations from simple 2,3-unsubstituted chromones or their enaminone precursors.

  通过简单的 2,3-未取代色酮或其烯胺酮前体的正式 [3 + 3] 环缩合反应，开发出了一种不同的、具有区域选择性的方法来制备融合吡啶。
• 3-Methoxalylchromone—a novel versatile reagent for the regioselective purine isostere synthesis
  作者：Satenik Mkrtchyan、Viktor O. Iaroshenko、Sergii Dudkin、Ashot Gevorgyan、Marcelo Vilches-Herrera、Gagik Ghazaryan、Dmitriy M. Volochnyuk、Dmytro Ostrovskyi、Zeeshan Ahmed、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1039/c0ob00379d

  日期：——

  The first synthesis of 3-methoxalylchromone was described. The reaction of the latter with electron-rich aminoheterocycles afforded a set of heteroannelated pyridines bearing a CO2Me substituent located at the α-position of the pyridine core.

  首次描述了 3-甲氧基苯丙酮的合成。后者与富含电子的氨基杂环反应后，得到了一组杂环吡啶，其吡啶核心的δ位上带有 CO2Me 取代基。
• 4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins
  作者：Viktor O. Iaroshenko、Friedrich Erben、Satenik Mkrtchyan、Ani Hakobyan、Marcelo Vilches-Herrera、Sergii Dudkin、Alina Bunescu、Alexander Villinger、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1016/j.tet.2011.08.030

  日期：2011.10

  4-chloro-3-(methoxalyl)coumarins react with electron-rich aminoheterocycles, dimethyl 1,3-acetonedicarboxylate, hydrazines, alkyl thioglycolates, and methyl sarcosinate to give a variety of 3,4-heteroannulated coumarins. The starting materials were prepared by the reaction of 4-hydroxycoumarin with trifluoroacetic anhydride and methyl 2-chloro-2-oxoacetate in the presence of trimethylsilylchloride.

  4-氯-3-（三氟乙酰基）-和4-氯-3-（甲氧烷基）香豆素与富含电子的氨基杂环，1,3-丙酮二羧酸二甲酯，肼，烷基硫代乙醇酸酯和肌氨酸甲酯合成各种3， 4异环化香豆素。在三甲基甲硅烷基氯的存在下，通过4-羟基香豆素与三氟乙酸酐和2-氯-2-氧代乙酸甲酯的反应制备起始原料。报道了NMR研究和X射线晶体学分析。