(9ci)-4-乙基-1H-咪唑-2-胺 | 19552-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: (9ci)-4-乙基-1H-咪唑-2-胺
• 中文别名: 4-乙基-1H-咪唑基-2-胺
• 英文名称: 2-Amino-4(5)-ethylimidazole
• 英文别名: 4-ethyl-1(3)H-imidazol-2-ylamine；4-Aethyl-1(3)H-imidazol-2-ylamin；4-ethyl-2-aminoimidazole；4-Ethyl-1H-imidazol-2-amine；5-ethyl-1H-imidazol-2-amine
• CAS: 19552-53-5
• 化学式: C₅H₉N₃
• 分子量: 111.147
• InChiKey: RFDQETHJZZCIIU-UHFFFAOYSA-N

物化性质

• 沸点：
  302.3±35.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  (9ci)-4-乙基-1H-咪唑-2-胺 在 sodium ethanolate 、 potassium carbonate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-Chloro-2-ethyl-1-[[2-methyl-3-(trifluoromethyl)phenyl]methyl]imidazo[1,2-a]pyrimidin-5-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of imidazo[1,2-a]pyrimidin-5(1H)-ones as a novel series of beta isoform selective phosphatidylinositol 3-kinase inhibitors

  摘要：

  A series of PI3K-beta selective inhibitors, imidazo[1,2-a]-pyrimidin-5(1H)-ones, has been rationally designed based on the docking model of the more potent R enantiomer of TGX-221, identified by a chiral separation, in a PI3K-beta homology model. Synthesis and SAR of this novel chemotype are described. Several compounds in the series demonstrated potent growth inhibition in a PTEN-deficient breast cancer cell line MDA-MB-468 under anchorage independent conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.092
• 作为产物：
  描述：

  N-(4-乙基-1H-咪唑-2-基)乙酰胺 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以86%的产率得到(9ci)-4-乙基-1H-咪唑-2-胺
  参考文献：
  名称：

  A Simple and Practical Synthesis of 2-Aminoimidazoles

  摘要：

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

  DOI：

  10.1021/jo00103a021

文献信息

• Two Uncommon Amino Acids obtained from Roseothricin
  作者：Koji Nakanishi、Toshiko Ito、Mamoru Ohashi、Ichiro Morimoto、Yoshimasa Hirata

  DOI：10.1246/bcsj.27.539

  日期：1954.8

  Roseothricin has been hydrolysed to give two uncommon amino acids, viz., β,ε-diaminocapric acid (I, β-lysine), and 2-amino-4(or 5)-(1-carboxy-1-hydroxy-2-amino)-ethyl-2-imidazoline (II, roseonine) as the sole ninhydrin positive products.

  玫瑰丝菌素经水解可得到两种不常见的氨基酸，即 β,ε-二氨基癸酸（I, β-赖氨酸）和 2-氨基-4（或 5）-(1-羧基-1-羟基-2-氨基）-乙基-2-咪唑啉（II，玫瑰碱）为唯一的茚三酮阳性产品。
• Reactions of 2-aminoimidazoles with aldehydes. Hydroxyalkylation and cycloaddition.
  作者：Ying-zi Xu、Kenichi Yakushijin、David A. Horne

  DOI：10.1016/s0040-4039(00)61576-9

  日期：1993.10

  The reaction between 2-aminoimidazoles and aldehydes affords mono- and disubstituted hydroxyalkylaminoimidazoles and tetrahydropurine derivatives. The formation of the tetrahydropurine is believed to proceed via an intermolecular hetero [2+4] cycloaddition between 2-aminoimidazole and its corresponding Schiff base.
• A Simple and Practical Synthesis of 2-Aminoimidazoles
  作者：Thomas L. Little、Stephen E. Webber

  DOI：10.1021/jo00103a021

  日期：1994.12

  A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.
• Synthesis and structure–activity relationships of imidazo[1,2-a]pyrimidin-5(1H)-ones as a novel series of beta isoform selective phosphatidylinositol 3-kinase inhibitors
  作者：Hong Lin、Karl Erhard、Mary Ann Hardwicke、Juan I. Luengo、James F. Mack、Jeanelle McSurdy-Freed、Ramona Plant、Kaushik Raha、Cynthia M. Rominger、Robert M. Sanchez、Michael D. Schaber、Mark J. Schulz、Michael D. Spengler、Rosanna Tedesco、Ren Xie、Jin J. Zeng、Ralph A. Rivero

  DOI：10.1016/j.bmcl.2012.01.092

  日期：2012.3

  A series of PI3K-beta selective inhibitors, imidazo[1,2-a]-pyrimidin-5(1H)-ones, has been rationally designed based on the docking model of the more potent R enantiomer of TGX-221, identified by a chiral separation, in a PI3K-beta homology model. Synthesis and SAR of this novel chemotype are described. Several compounds in the series demonstrated potent growth inhibition in a PTEN-deficient breast cancer cell line MDA-MB-468 under anchorage independent conditions. (C) 2012 Elsevier Ltd. All rights reserved.