(4-amino-2-methylquinolin-3-yl)methanol | 75353-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (4-amino-2-methylquinolin-3-yl)methanol
• 英文别名: amino-4 hydroxymethyl-3 methyl-2 quinoleine；4-amino-3-hydroxymethyl-2-methylquinoline
• CAS: 75353-57-0
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: DBJOVOJZLWALLL-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  410.1±40.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-amino-2-methylquinolin-3-yl)methanol 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到4-amino-2-methylquinoline-3-carbaldehyde
  参考文献：
  名称：

  Godard, Alain; Queguiner, Guy, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 465 - 473

  摘要：

  DOI：
• 作为产物：
  描述：

  amino-4 methyl-2 quinoleinecarboxylate de methyle-3 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到(4-amino-2-methylquinolin-3-yl)methanol
  参考文献：
  名称：

  Godard, Alain; Queguiner, Guy, Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 465 - 473

  摘要：

  DOI：

文献信息

• Interesting Results of Catalytic Hydrogenation of 3-(2-Nitrophenyl)isoxazoles and 3-(Nitrophenyl)-4,5-dihydroisoxazoles
  作者：S. Batra、V. Singh、S. Madapa、G. Yadav、P. Maulik

  DOI：10.1055/s-2006-942388

  日期：2006.6

  hydrogenolysis of substituted 3-(2-nitrophenyl)isoxazoles, irrespective of substitution on the isoxazole ring, invariably leads to reduction of the nitro to the amino group with concomitant regiospecific ring closure to yield substituted 4-aminoquinolines. In contrast similar hydrogenation of 3-(2-, 3-, and 4-nitrophenyl)-4,5-dihydroisoxazoles (2-isoxazolines) results in reduction of the nitro group only

  取代的 3-(2-硝基苯基) 异恶唑的钯碳辅助氢解，无论异恶唑环上的取代如何，都会导致硝基还原为氨基，同时伴随区域特异性闭环产生取代的 4-氨基喹啉。相比之下，类似的 3-(2-、3- 和 4-硝基苯基)-4,5-二氢异恶唑 (2-异恶唑啉) 的氢化导致硝基还原，仅保留二氢异恶唑环，得到相应的 3- (氨基苯基)-4,5-二氢异恶唑。
• A Structure-Based Design Approach to the Development of Novel, Reversible AChE Inhibitors
  作者：Caroline Doucet-Personeni、Philip D. Bentley、Rodney J. Fletcher、Adrian Kinkaid、Gitay Kryger、Bernard Pirard、Anne Taylor、Robin Taylor、John Taylor、Russell Viner、Israel Silman、Joel L. Sussman、Harry M. Greenblatt、Terence Lewis

  DOI：10.1021/jm010826r

  日期：2001.9.1

  Chimeras of tacrine and m-(N,N,N-Trimethylammonio)trifluoroacetophenone (1) were designed as novel, reversible inhibitors of acetylcholinesterase. On the basis of the X-ray structure of the apoenzyme, a molecular modeling study determined the favored attachment positions on the 4-aminoquinoline ring (position 3 and the 4-amino nitrogen) and the favored lengths of a polymethylene link between the two moieties (respectively 5-6 and 4-5 sp(3) atoms). Seven compounds matching these criteria were synthesized, and their inhibitory potencies were determined to be in the low nanomolar range. Activity data for close analogues lacking some of the postulated key features showed that our predictions were correct. In addition, a subsequent crystal structure of acetylcholinesterase complexed with the most active compound 27 was in good agreement with our model. The design strategy is therefore validated and can now be developed further.
• GODARD A.; QUEGUINER G., J. HETEROCYCLIC. CHEM., 1980, 17, NO 3, 465-473
  作者：GODARD A.、 QUEGUINER G.

  DOI：——

  日期：——