3,4-dimethoxyphenyl(quinolin-3-yl)methanone | 1187164-00-6

• 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: 3,4-dimethoxyphenyl(quinolin-3-yl)methanone
• 英文别名: (3,4-Dimethoxyphenyl)(quinolin-3-yl)methanone；(3,4-dimethoxyphenyl)-quinolin-3-ylmethanone
• CAS: 1187164-00-6
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: GMVZHKQFCTYIFB-UHFFFAOYSA-N

物化性质

• 沸点：
  475.6±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(2-甲酰基苯基)-4-甲基苯磺酰胺 、 1-(3,4-dimethoxyphenyl)prop-2-yn-1-one 在 三苯基膦 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 1.58h， 以93%的产率得到3,4-dimethoxyphenyl(quinolin-3-yl)methanone
  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

• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODE-GENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Sheridan Joseph M.

  公开号：US20140031547A1

  公开（公告）日：2014-01-30

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• CASEIN KINASE 1delta (CK 1delta) INHIBITORS AND THEIR USE IN THE TREATMENT OF NEURODEGENERATIVE DISEASES SUCH AS TAUOPATHIES
  申请人：Electrophoretics Limited

  公开号：US20160354375A1

  公开（公告）日：2016-12-08

  The invention relates to pharmaceutical compositions comprising casein kinase 1 delta (CK1δ) and to the use of said inhibitors in the treatment of neurodegenerative disorders such as Alzheimer's disease.
• 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.