1-[2-(4-chlorophenyl)ethyl]-1H-imidazole | 56643-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[2-(4-chlorophenyl)ethyl]-1H-imidazole
• 英文别名: 1-(4-chlorophenethyl)-1H-imidazole；1-(4-chloro-phenethyl)-1H-imidazole；1-(4-Chlor-phenaethyl)-1H-imidazol；1H-Imidazole, 1-[2-(4-chlorophenyl)ethyl]-；1-[2-(4-chlorophenyl)ethyl]imidazole
• CAS: 56643-90-4
• 化学式: C₁₁H₁₁ClN₂
• 分子量: 206.675
• InChiKey: MOYFWXULYXUBOS-UHFFFAOYSA-N

物化性质

• 沸点：
  159-161 °C(Press: 0.1 Torr)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯苯乙醇 在 三溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 1-[2-(4-chlorophenyl)ethyl]-1H-imidazole
  参考文献：
  名称：

  Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a range of 4-substituted phenyl alkyl imidazole-based inhibitors of the enzyme complex 17α-hydroxylase/17,20-lyase (P45017α)

  摘要：

  We report the preliminary results of the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a number of phenyl alkyl imidazole-based compounds as inhibitors of the two components of 17 alpha-hydroxylase/17,20-lyase (P450(17 alpha)), that is, 17 alpha-hydroxylase (17 alpha-OHase) and 17,20-lyase (lyase). The results show that N-3-(4-bromophenyl) propyl imidazole (12) (IC50 = 2.95 mu M against 17 alpha-OHase and IC50 = 0.33 mu M against lyase) is the most potent compound within the current study, in comparison to ketoconazole (KTZ) (IC50 = 3.76 mu M against 17 alpha-OHase and IC50 = 1.66 mu M against lyase). Modelling of these compounds suggests that the length of the alkyl chain enhances the interaction between the inhibitor and the area of the active site corresponding to the C(3) area of the steroid backbone, thereby increasing potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.092

文献信息

• Syntheses of 1-substituted 1,2,4-triazoles, imidazoles and benzimidazoles
  作者：Abdollah Sharifian、Kaykavoos Parang、Hassan Zorrieh-Amirian、Mehrdad Nazarinia、Abbas Shafiee

  DOI：10.1002/jhet.5570310621

  日期：1994.11

  Substituted 2-phenethyl-1,2,4-triazoles, 1-phenethylimidazoles 3 and 1-phenethylbenzimidazoles 5 were synthesized from the reaction of compound 8 with tri-n-butyltin hydride in good yield. The reaction of substituted-2-phenethyl halide with 1H-1,2,4-triazoles, imidazoles and benzimidazoles gave a low yield. The yield was increased by the use of substituted-2-phenethyl p-toluensulfonate.

  取代的2-苯乙基-1,2,4-三唑，1- phenethylimidazoles 3和1- phenethylbenzimidazoles 5从化合物的反应合成8与三Ñ -butyltin氢化以良好的收率。取代的-2-苯乙基卤化物与1 H -1,2,4-三唑，咪唑和苯并咪唑的反应收率低。通过使用对甲苯磺酸取代的2-苯乙基酯提高产率。
• Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu₃SnH
  作者：Mairéad A. Clyne、Fawaz Aldabbagh

  DOI：10.1039/b512729g

  日期：——

  Six-membered photochemical cyclisations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. The decrease in yield of cyclisation products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the sigma-imidazol-2-yl radicals. The seven-membered

  与碘化氢化锡介导的反应相比，2-碘-N-（2-芳基乙基）咪唑的六元光化学环化在区域选择性上以更高的产率进行。芳基环上含有高度失活的取代基的5,6-二氢咪唑并[2,1-a]异喹啉环化产物的收率降低，证实了sigma-咪唑-2-基的亲电性质。七元环化仅在光化学条件下才能成功，因为氢化锡会发生自由基还原。5,6-二氢咪唑并[2,1-a]异喹啉在硝酸和硫酸的2和8位发生硝化。
• Studies of Imidazoles. VII. Substituted 1-Phenethylimidazoles and Related Compounds^*,1
  作者：W. N. CANNON、C. E. POWELL、R. G. JONES

  DOI：10.1021/jo01362a008

  日期：1957.11