1-(6-methoxyquinolin-3-yl)ethanone | 1396547-27-5

• 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: 1-(6-methoxyquinolin-3-yl)ethanone
• CAS: 1396547-27-5
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: AXMZEKYEGPHFDC-UHFFFAOYSA-N

物化性质

• 沸点：
  343.9±22.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-对甲苯磺酰基-2-甲酰基-4-甲氧基苯胺 、 3-丁炔-2-酮 在 三苯基膦 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 1.58h， 以92%的产率得到1-(6-methoxyquinolin-3-yl)ethanone
  参考文献：
  名称：

  One-Pot Phosphine-Catalyzed Syntheses of Quinolines

  摘要：

  In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the beta-phosphonium enoate alpha-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.

  DOI：

  10.1021/jo3015825

文献信息

• Selective reductive annulation reaction for direct synthesis of functionalized quinolines by a cobalt nanocatalyst
  作者：Rong Xie、Guang-Peng Lu、Huan-Feng Jiang、Min Zhang

  DOI：10.1016/j.jcat.2020.01.034

  日期：2020.3

  funcitonalized quinolines with the merits of broad substrate scope, good functional group tolerance, excellent hydrogen transfer selectivity, reusable earth-abundant metal catalyst, and operational simplicity. The developed chemistry paves the ways for further design of hydrogen transfer-mediated coupling reactions by developing heterogeneous catalysts with suitable supports.

  由于喹啉的广泛应用，对这类产品的选择性结构的寻找一直是科学界的一个有吸引力的主题。在此，通过开发新的N掺杂ZrO 2@C负载的钴纳米材料，已成功地用作有效的催化剂，用于通过炔烃和炔酮还原环氧化2-硝基芳基羰基。催化转化可以合成具有宽底物范围，良好的官能团耐受性，优异的氢转移选择性，可重复使用的富地球金属催化剂以及操作简便等优点的功能齐全的喹啉。通过开发具有合适载体的非均相催化剂，已开发的化学方法为进一步设计氢转移介导的偶联反应铺平了道路。
• [EN] N1/N2-LACTAM ACETYL-CoA CARBOXYLASE INHIBITORS<br/>[FR] INHIBITEURS DE LA N1/N2-LACTAME ACÉTYL-COA CARBOXYLASE
  申请人：PFIZER

  公开号：WO2012056372A1

  公开（公告）日：2012-05-03

  The invention provides a compound of Formula (I); or a pharmaceutically acceptable salt thereof; wherein G is Formula (II), Formula (III), Formula (IV) and Formula (V) R1, R2 and R3 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl-CoA carboxylase enzyme(s) in an animal.
• One-Pot Phosphine-Catalyzed Syntheses of Quinolines
  作者：San Khong、Ohyun Kwon

  DOI：10.1021/jo3015825

  日期：2012.9.21

  In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the beta-phosphonium enoate alpha-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.