N-(2-bromoethyl)propanamide | 1081542-04-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-bromoethyl)propanamide
• CAS: 1081542-04-2
• 化学式: C₅H₁₀BrNO
• 分子量: 180.044
• InChiKey: FFXCHTSFULCCJK-UHFFFAOYSA-N

物化性质

• 熔点：
  93 °C(Solv: benzene (71-43-2))
• 沸点：
  293.6±23.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-bromoethyl)propanamide 在 trimethylsilyl polyphosphate 作用下， 以 二氯甲烷 为溶剂， 反应 1.38h， 生成 1-(4-chlorophenyl)-2-ethyl-4,5-dihydro-1H-imidazol
  参考文献：
  名称：

  Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1H-imidazoles

  摘要：

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.

  DOI：

  10.1080/00397911.2011.552155
• 作为产物：
  描述：

  2-溴乙胺氢溴酸盐 、 丙酸酐 生成 N-(2-bromoethyl)propanamide
  参考文献：
  名称：

  Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1H-imidazoles

  摘要：

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.

  DOI：

  10.1080/00397911.2011.552155

文献信息

• An Efficient Synthesis of 1-Acyl-3-arylimidazolidines Catalyzed by Montmorillonite K-10 Clay under Microwave Irradiation
  作者：Alejandra Salerno、Isabel Perillo、María Verónica Corona、María Cristina Caterina

  DOI：10.3987/com-08-11565

  日期：——

  The synthesis of 1-acyl-3-arylimidazolidines were performed by reaction of N-acyl-N -arylethylenediamines with formaldehyde and Montmorillonite clay K-10 as a catalyst under microwave irradiation. INTRODUCTION Tetrahydroimidazoles (imidazolidines) are cyclic aminals of pharmacological interest due to the bioactivity shown by some members which is closely related to the substitution type. The most studied

  1-酰基-3-芳基咪唑烷类化合物的合成是通过N-酰基-N-芳基乙二胺与甲醛和蒙脱土K-10作为催化剂在微波辐射下反应进行的。引言 四氢咪唑类（咪唑烷类）是具有药理学意义的环状缩醛胺，因为一些成员表现出的生物活性与取代类型密切相关。研究最多的化合物是那些带有烷基或芳基的 N,N-二取代化合物，有时会被官能化。因此，文献中已经描述了大量具有多种特性的这些化合物，例如雌激素活性和乳腺肿瘤抑制、抗炎和镇痛活性。还报告了杀菌剂、杀菌剂和抗病毒活性。另一方面，由于咪唑烷的疏水性，它们可用于增加前药形式的生物活性前体的生物利用度，并且它们已被用作药理活性乙二胺或羰基化合物的载体。它们还与辅酶 N,N-亚甲基四氢叶酸密切相关，后者在甲醛的氧化水平上参与单碳转移。从化学的角度来看，这类化合物的合成和研究令人感兴趣，它们是具有乙二胺结构单元的环状和非环状化合物的合成中间体。因此，咪唑烷的脱氢导致 4,5-二氢-1H-咪唑盐和它们选择性还原为
• Synthesis and Synthetic Applications of 1-Aryl-2-alkyl-4,5-dihydro-1<i>H</i>-imidazoles
  作者：Ana M. Reverdito、Isabel A. Perillo、Alejandra Salerno

  DOI：10.1080/00397911.2011.552155

  日期：2012.7.15

  An easy synthesis of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles 1 by cyclo-condensation of N-acyl-N'-arylethylenediamines 2 is described. Such precursors were synthesized by aminolysis of the corresponding N-(2-bromoethyl)amides 3. Cyclizations were performed using trimethylsilyl polyphosphate as a mild dehydrating agent, under microwave irradiation. Chemical properties of 1-aryl-2-alkyl-4,5-dihydro-1H-imidazoles, typical of the amidine system, were studied. Reduction of dihydroimidazoles with sodium cyanoborohydride leads regiospecifically to N-alkyl-N'-arylethylenediamines 4, and nucleophilic attack to methyl iodide leads to the corresponding 1-aryl-2-alkyl-3-methyl-4,5-dihydro-1H-imidazolium salts 5.