N-丁基嘧啶-2-胺 | 10132-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: N-丁基嘧啶-2-胺
• 英文名称: N-butylpyrimidin-2-amine
• 英文别名: 2-Butylamino-pyrimidin；2-(butylamino)pyrimidine
• CAS: 10132-28-2
• 化学式: C₈H₁₃N₃
• mdl: MFCD00956320
• 分子量: 151.211
• InChiKey: HSSUQMDTTMMOGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C(Solv: ligroine (8032-32-4))
• 沸点：
  261.1±23.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-丁基嘧啶-2-胺 在 4-二甲氨基吡啶 、 磷酸 、 一水合肼 作用下， 以 水 、 乙腈 为溶剂， 反应 5.25h， 生成 1-丁基-5-苯基咪唑-2-胺
  参考文献：
  名称：

  Structure−Activity Relationship of 4(5)-Aryl-2-amino-1H-imidazoles, N1-Substituted 2-Aminoimidazoles and Imidazo[1,2-a]pyrimidinium Salts as Inhibitors of Biofilm Formation by Salmonella Typhimurium and Pseudomonas aeruginosa

  摘要：

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.

  DOI：

  10.1021/jm1011148
• 作为产物：
  描述：

  2-<(1-benzotriazol-1-yl)butylamino>pyrimidine 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以98%的产率得到N-丁基嘧啶-2-胺
  参考文献：
  名称：

  Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila, Journal of the Chemical Society. Perkin transactions I, 1987, p. 805 - 810

  摘要：

  DOI：

文献信息

• Co(II) PCP Pincer Complexes as Catalysts for the Alkylation of Aromatic Amines with Primary Alcohols
  作者：Matthias Mastalir、Gerald Tomsu、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1021/acs.orglett.6b01647

  日期：2016.7.15

  Efficient alkylations of amines by alcohols catalyzed by well-defined Co(II) complexes are described that are stabilized by a PCP ligand (N,N′-bis(diisopropylphosphino)-N,N′-dimethyl-1,3-diaminobenzene) based on the 1,3-diaminobenzene scaffold. This reaction is an environmentally benign process implementing inexpensive, earth-abundant nonprecious metal catalysts and is based on the acceptorless alcohol

  描述了由定义明确的Co（II）配合物催化的醇对胺的有效烷基化作用，并通过PCP配体（基于N，N'-双（二异丙基膦基）-N，N'-二甲基-1,3-二氨基苯）稳定化在1,3-二氨基苯支架上 该反应是一种环境友好的方法，采用廉价的，富含地球的非贵金属催化剂，并且基于无受体醇脱氢概念。一系列伯醇和芳族胺以良好或优异的分离收率有效地转化为单-N-烷基化胺。
• Palladium-catalyzed remote C–H functionalization of 2-aminopyrimidines
  作者：Animesh Das、Akash Jana、Biplab Maji

  DOI：10.1039/d0cc00575d

  日期：——

  A straightforward strategy was developed for the arylation and olefination at the C5-position of the N-(alkyl)pyrimidin-2-amine core with readily available aryl halides and alkenes, respectively. This approach was highly regioselective, and the transformation was achieved based on two different (Pd(ii)/Pd(iv)) and (Pd(0)/Pd(ii)) catalytic cycles.

  针对N-（烷基）嘧啶-2-胺核心的C5-位的芳基化和烯化反应，开发了一种简单的策略，分别使用易得的芳基卤化物和烯烃。这种方法是高度区域选择性的，并且基于两个不同的（Pd（ii）/ Pd（iv））和（Pd（0）/ Pd（ii））催化循环实现了转化。
• Ag(i) complexes with alkylidene-bis(2-aminopyrimidines) as building units for discrete metallomacrocyclic frames. A structural and solution study
  作者：Angel García-Raso、Juan J. Fiol、Andrés Tasada、Francisca M. Albertí、Elies Molins、Manuel G. Basallote、María A. Máñez、María J. Fernández-Trujillo、David Sánchez

  DOI：10.1039/b508260a

  日期：——

  Alkylidene-bis(2-aminopyrimidines) (pyr2Cx, x = 2–5) are useful ligands to interact with Ag(I) yielding discrete metallocycles. Crystal structures of the [(pyr2C2)Ag(NO3)]2 and [(H-pyr2C4)Ag(NO3)2]2 have been isolated where each macrocyclic moiety interacts with their surroundings through weak interactions, yielding 3D discrete structures, On the other hand, the solution study shows that the equilibrium constants for the formation of Ag(pyr2Cx)+ complexes are higher than the literature values for Ag(I) complexes with single pyrimidines, although the differences could be explained by invoking the solid-state structures of the Ag(I)–pyr2Cx complexes.

  烯叉双(2-氨基嘧啶)(pyr2Cx, x = 2–5)是有用的配体，能与Ag(I)生成离散的金属环。分离得到了[(pyr2C2)Ag(NO3)]2和[(H-pyr2C4)Ag(NO3)2]2的晶体结构，其中每个大环部分都通过弱相互作用与其周围环境相互作用，形成三维离散结构。另一方面，溶液研究显示，Ag(pyr2Cx)+配合物的形成平衡常数高于已知文献中单嘧啶Ag(I)配合物的值，尽管这种差异可以通过考虑Ag(I)-pyr2Cx配合物的固态结构来解释。
• Air Stable Iron(II) PNP Pincer Complexes as Efficient Catalysts for the Selective Alkylation of Amines with Alcohols
  作者：Matthias Mastalir、Berthold Stöger、Ernst Pittenauer、Michael Puchberger、Günter Allmaier、Karl Kirchner

  DOI：10.1002/adsc.201600689

  日期：2016.12.7

  A series of well‐defined iron(II) complexes of the types [Fe(PNP)Br2] and [Fe(PNP)(CO)Br2] with PNP pincer ligands based on triazine and pyridine backbones were prepared and fully characterized. These complexes were tested as catalysts for the alkylation of amines by alcohols. The high‐spin complexes [Fe(PNP)Br2] are catalytically inactive. The low‐spin complexes [Fe(PNP)(CO)Br2] bearing a carbonyl

  制备了一系列具有明确定义的铁（II）配合物，其类型为[Fe（PNP）Br 2 ]和[Fe（PNP）（CO）Br 2 ]，具有基于三嗪和吡啶骨架的PNP钳形配体。测试了这些络合物作为胺被醇烷基化的催化剂。高自旋络合物[Fe（PNP）Br 2 ]具有催化活性。带有羰基共配体的低自旋络合物[Fe（PNP）（CO）Br 2 ]有效地和选择性地将伯醇以及芳族和苄基胺选择性地转化为单N烷基化胺，分离率高至优异。给出了机械的建议。
• 用于相变存储材料的氨基嘧啶Ge(Ⅱ)前质体 及其制备方法
  申请人：江南大学

  公开号：CN104341355B

  公开（公告）日：2017-02-08

  本发明涉及一种用于相变存储材料的氨基嘧啶Ge(II)前质体，该前质体以氨基嘧啶及其衍生物为配体，依以下方法制备：(1)将氨基密啶及其衍生物溶解在反应溶剂中，‑78～0℃搅拌条件下加入烷基锂溶液，氨基嘧啶或其衍生物与烷基锂摩尔比1.0∶1.0～1.2，恢复室温继续搅拌至固体产生，过滤得到锂盐；(2)将步骤(1)得到的锂盐与甲苯混合，‑78～0℃条件下以锂盐与金属锗摩尔比2.0∶1.0～1.2滴加到二氯化锗的甲苯溶液中，升温至室温；(3)将步骤(2)得到的混合物过滤浓缩，滤渣用二氯甲烷提取，收集滤液，‑50～0℃低温结晶，得到所述的氨基嘧啶Ge(II)前质体。本发明合成方法简单，制备的前质体热稳定性高，挥发性好，成膜性能优良，是制备相变存储材料潜在的重要前质体。