2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one | 95987-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 2-(imidazol-1-ylmethyl)-1-tetralone；2-(imidazol-1-ylmethyl)-3,4-dihydro-2H-naphthalen-1-one
• CAS: 95987-34-1
• 化学式: C₁₄H₁₄N₂O
• 分子量: 226.278
• InChiKey: MTKYOLUCLMKQLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 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：

  2-imidazol-1-ylmethyl-3,4-dihydro-2H-naphthalen-1-one 在 palladium on activated charcoal 高氯酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 30.0 ℃ 、500.0 kPa 条件下， 以52%的产率得到2-(imidazol-1-ylmethyl)-tetralin
  参考文献：
  名称：

  作为 P450 芳香族、P450 17 和 P450 TxA2 抑制剂的唑取代四氢萘的合成和评价

  摘要：

  寻找用于治疗雌激素和雄激素依赖性癌症以及预防转移的潜在药物、四氢萘酮、四氢萘和在苯核上带有 OCH3 取代基和咪唑 - 4 - 基、咪唑 - 1- 的二氢萘基或 1,2,4-三唑-1-基取代基在 2-位合成，在环之间有和没有 C1-间隔物（化合物 2-26）。在体外测试了这些化合物对三种靶酶 P450 arom（人胎盘微粒体）、P450 17（大鼠睾丸微粒体）和 P450 TxA2（柠檬酸化人全血）的抑制作用。为了检查选择性，在体外进一步测试了一些化合物对 P450 18（牛肾上腺线粒体）、P450 see（牛肾上腺线粒体）和皮质激素形成（醛固酮、皮质酮；ACTH 刺激的大鼠肾上腺组织）的抑制。体内，

  DOI：

  10.1002/ardp.19963290506
• 作为产物：
  描述：

  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

• 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.
• A New Application of Mannich Bases
  作者：D. F. Rane、A. G. Fishman、R. E. Pike

  DOI：10.1055/s-1984-30938

  日期：——
• RANE, D. F.;FISHMAN, A. G.;PIKE, R. E., SYNTHESIS, BRD, 1984, N 8, 694-695
  作者：RANE, D. F.、FISHMAN, A. G.、PIKE, R. E.

  DOI：——

  日期：——