1-(3-Hydroxy-2-methyl-3-phenylprop-2-yl)-imidazol | 24155-53-1

• 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-(3-Hydroxy-2-methyl-3-phenylprop-2-yl)-imidazol
• 英文别名: 2-(1H-imidazol-1-yl)-2-methyl-1-phenylpropan-1-ol；2-imidazol-1-yl-2-methyl-1-phenyl-propan-1-ol；I(2),I(2)-Dimethyl-I+/--phenyl-1H-imidazole-1-ethanol；2-imidazol-1-yl-2-methyl-1-phenylpropan-1-ol
• CAS: 24155-53-1
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: QNJYGLHYCGQIMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-(3-Hydroxy-2-methyl-3-phenylprop-2-yl)-imidazol 反应 15.0h， 以79%的产率得到(R,S)-1-Acetoxy-2-(1-imidazolyl)-2-methyl-1-phenylpropane
  参考文献：
  名称：

  Effects of anti-ecdysteroid azole analogues of metyrapone on the larval development of the fleshfly,Neobellieria bullata

  摘要：

  AbstractBased on our previous finding that PIM (phenyl‐imidazolyl‐metyra‐pon; 2‐(1‐imidazolyl)‐2‐methyl‐1‐phenylpropan‐1‐one, 1) is a strong inhibitor of ecdysone 20‐monooxygenase (IC50 = 7.89 × 10−7 M) from the fleshfly, Neobellieria bullata (Parker) and has also a good toxic action in vivo against this insect, 17 imidazole and 1,2,4‐triazole analogues of metyrapone were synthesized and evaluated for their action against N. bullata larvae in terms of toxicity, length of larval development, weight of the puparium as well as special symptoms, i.e. malformations of the anterior and posterior spiracles, and of the mandibles. The introduction of p‐methoxy (LC50 = 49 mg kg−1 in diet) or p‐chloro (LC50 = 97 mg kg−1) substituents on the benzene ring of PIM resulted in a significant increase in toxicity compared to that of metyrapone (LC50 = 561 mg kg−1) and PIM (LC50 = 148 mg kg−1). The hybridization state of the carbon atom adjacent to the benzene ring was not an important factor for toxicity because the acetoxy derivative (13) was almost as toxic as PIM. At least one methyl group was required on the carbon atom adjacent to the azole ring to maintain activity, while an ethyl group (4) enhanced the toxic effect. At the applied doses some compounds including metyrapone itself, extended the duration of the larval development. Only metyrapone and PIM decreased the puparium weight. Several derivatives induced lethal malformations of mandibles as well as the anterior and posterior spiracles.

  DOI：

  10.1002/ps.2780440304
• 作为产物：
  描述：

  2-溴-2-甲基苯丙酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 1-(3-Hydroxy-2-methyl-3-phenylprop-2-yl)-imidazol
  参考文献：
  名称：

  手性三齿配体的钌配合物催化的大体积酮的对映选择性加氢和转移加氢

  摘要：

  报道了对一类新型三齿-Ru配合物催化的叔烷基酮的对映选择性加氢的研究。与广泛研究的[RuCl 2（diphos）（二伯胺）]配合物相比，这种新型的氢化催化剂可将这些反应性较低的笨重酮平稳还原，其ee最高可达94％ 。相同的催化剂体系还可以选择性地还原其他潜在有问题的底物，例如庞大的杂环酮。通常对于加压氢化催化剂，在转移氢化条件下可以获得相似的对映选择性。转移氢化比压力氢化稍慢，但是这个缺点很容易克服，因为我们发现上述酮的微波加速转移氢化在约90°C的20分钟内发生，其选择性与在压力下获得的选择性相似。氢化系统。

  DOI：

  10.1002/chem.200801929