5-chloro-2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one | 1093231-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-chloro-2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 5-chloro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 1093231-54-9
• 化学式: C₁₄H₁₃ClN₂O
• 分子量: 260.723
• InChiKey: ILDDRPMUYVAQHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one 在 盐酸羟胺 、 potassium hydrogencarbonate 作用下， 以 乙醇 、 水 为溶剂， 以70%的产率得到(Z)-5-chloro-2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one oxime
  参考文献：
  名称：

  Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials☆

  摘要：

  A series of novel (Z)- and (E)-2-imidazolo-/triazolo-methyl tetrahydronaphthyl oxime ethers (7-28) were synthesized as conformationally constrained analogues of oxiconazole and evaluated for antifungal and antibacterial activities. Many of these derivatives exhibited potent antibacterial activity and surprisingly none of them was active against fungal strains. The SAR studies showed that imidazole oxime ethers were more active than the corresponding triazole oxime ethers. Imidazole derivatives 8, 11, 12, 15, 18, 19, 21 and 23 exhibited high inhibitory activity with 1.56-0.39 mu g/mL MIC values against Klebsiella pneumoniae, Escherichia coli and Staphylococcus aureus. These compounds represent new structure scaffolds that can be further optimized to give new antibacterial agents with structures significantly different from those of existing classes of antibiotics. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.006
• 作为产物：
  描述：

  5-chloro-2-hydroxymethyl-2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以100%的产率得到5-chloro-2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Proline-catalyzed facile access to Mannich adducts using unsubstituted azoles

  摘要：

  A novel and facile method for the direct construction of C-C-N bond with unsubstituted azoles under Mannich conditions is developed for the first time. The reaction is catalyzed efficiently by.-proline to give the Mannich adducts 1a-10b in DMSO, whereas in water, insertion of two successive bonds, C-C-N and C-C-O occurred to give compounds 11a-20b. The latter are deformylated readily into the desired products 1a-10b Under basic conditions. Mechanistic aspects for the formation of these products are discussed. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.09.155

文献信息

• Proline-catalyzed facile access to Mannich adducts using unsubstituted azoles
  作者：Nagarapu Srinivas、Kalpana Bhandari

  DOI：10.1016/j.tetlet.2008.09.155

  日期：2008.12

  A novel and facile method for the direct construction of C-C-N bond with unsubstituted azoles under Mannich conditions is developed for the first time. The reaction is catalyzed efficiently by.-proline to give the Mannich adducts 1a-10b in DMSO, whereas in water, insertion of two successive bonds, C-C-N and C-C-O occurred to give compounds 11a-20b. The latter are deformylated readily into the desired products 1a-10b Under basic conditions. Mechanistic aspects for the formation of these products are discussed. (c) 2008 Elsevier Ltd. All rights reserved.
• Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials☆
  作者：Kalpana Bhandari、Nagarapu Srinivas、G.B. Shiva Keshava、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2008.01.006

  日期：2009.1

  A series of novel (Z)- and (E)-2-imidazolo-/triazolo-methyl tetrahydronaphthyl oxime ethers (7-28) were synthesized as conformationally constrained analogues of oxiconazole and evaluated for antifungal and antibacterial activities. Many of these derivatives exhibited potent antibacterial activity and surprisingly none of them was active against fungal strains. The SAR studies showed that imidazole oxime ethers were more active than the corresponding triazole oxime ethers. Imidazole derivatives 8, 11, 12, 15, 18, 19, 21 and 23 exhibited high inhibitory activity with 1.56-0.39 mu g/mL MIC values against Klebsiella pneumoniae, Escherichia coli and Staphylococcus aureus. These compounds represent new structure scaffolds that can be further optimized to give new antibacterial agents with structures significantly different from those of existing classes of antibiotics. (C) 2008 Elsevier Masson SAS. All rights reserved.