ethyl 1-(phenyl-3-dihydroxyboranyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate | 694489-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 1-(phenyl-3-dihydroxyboranyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate
• 英文别名: ethyl 1-(3-phenylboronic acid)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate；1-[3-(Dihydroxyboryl)phenyl]-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid ethyl ester；[3-(3-ethoxycarbonyl-4-oxo-1,8-naphthyridin-1-yl)phenyl]boronic acid
• CAS: 694489-60-6
• 化学式: C₁₇H₁₅BN₂O₅
• 分子量: 338.127
• InChiKey: YMVFANMSFGZNRT-UHFFFAOYSA-N

物化性质

• 熔点：
  273 °C
• 沸点：
  569.9±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 1-(phenyl-3-dihydroxyboranyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate 在 bis(η3-allyl-μ-chloropalladium(II)) sodium hydroxide 、 三叔丁基膦 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 8.0h， 生成 1-{3-[6-(1-hydroxy-1-methylethyl)-1-oxidopyridin-3-yl]phenyl}-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylic acid
  参考文献：
  名称：

  Practical application of new catalytic methods: a concise synthesis of a potent PDE IV inhibitor

  摘要：

  An efficient synthesis of a potent PDE IV inhibitor 1 is described. The synthesis is highlighted by two practical and efficient catalytic reactions: a highly selective catalytic palladium rnediated carbonylation of the pyridine side chain and an efficient palladiumcatalyzed Suzuki-Miyaura coupling of a chi oropyridi ne-N-oxide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.143
• 作为产物：
  描述：

  2-氯烟酰氯 、 3-(N,N-二甲基氨基)丙烯酸乙酯 、 3-氨基苯基硼酸盐酸盐 在 三乙胺 、 potassium phosphate 作用下， 以 甲苯 、 N,N-二甲基乙酰胺 为溶剂， 反应 23.0h， 以78%的产率得到ethyl 1-(phenyl-3-dihydroxyboranyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxylate
  参考文献：
  名称：

  Practical application of new catalytic methods: a concise synthesis of a potent PDE IV inhibitor

  摘要：

  An efficient synthesis of a potent PDE IV inhibitor 1 is described. The synthesis is highlighted by two practical and efficient catalytic reactions: a highly selective catalytic palladium rnediated carbonylation of the pyridine side chain and an efficient palladiumcatalyzed Suzuki-Miyaura coupling of a chi oropyridi ne-N-oxide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.143

文献信息

• Method of preparing inhibitors of phosphodiesterase-4
  申请人：——

  公开号：US20040102472A1

  公开（公告）日：2004-05-27

  In one aspect, the present invention is directed to a one pot method of preparing intermediates of Formula V, which are useful in making inhibitors of phosphodiesterase-4: 1 The present invention is also directed to a method of preparing phosphodiesterase inhibitors comprising the Formula 2

  在一个方面，本发明涉及一种制备Formula V中间体的一锅法，该中间体在制备磷酸二酯酶-4抑制剂时非常有用： 另外，本发明还涉及一种制备磷酸二酯酶抑制剂的方法，包括Formula 2。
• 4-oxo-1-(3-substituted phenyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide phosphodiesterase-4 inhibitor and a method of preparing same
  申请人：Dube Daniel

  公开号：US20070099951A1

  公开（公告）日：2007-05-03

  The invention is directed to a compound of the structural formula (22) crystal form of structural formulae (21) and its free acid, pharmaceutical compositions comprising these compounds and methods of preparing and using these compounds.

  该发明涉及结构式（22）晶体形式的化合物，结构式（21）及其游离酸，包括这些化合物的药物组合物以及制备和使用这些化合物的方法。
• 4-Oxo-1-3-Substituted Phenyl-1,4-Dihydro-1,8-Napthyridene-3-Carboxamide Phosphodiesterase-4 Inhibitor and a Method of Preparing Same
  申请人：Cameron Mark

  公开号：US20090105479A1

  公开（公告）日：2009-04-23

  The invention is directed to a compound of the structural formula (22) (22) crystal form of structural formulae (21) and its free acid, pharmaceutical compositions comprising these compounds and methods of preparing and using these compounds.

  该发明涉及结构式（22）的化合物，结构式（21）的晶型及其游离酸，包括这些化合物的药物组合物以及制备和使用这些化合物的方法。
• Practical application of new catalytic methods: a concise synthesis of a potent PDE IV inhibitor
  作者：Jennifer Albaneze-Walker、Jerry A. Murry、Arash Soheili、Scott Ceglia、Shawn A. Springfield、Charles Bazaral、Peter G. Dormer、David L. Hughes

  DOI：10.1016/j.tet.2005.03.143

  日期：2005.6

  An efficient synthesis of a potent PDE IV inhibitor 1 is described. The synthesis is highlighted by two practical and efficient catalytic reactions: a highly selective catalytic palladium rnediated carbonylation of the pyridine side chain and an efficient palladiumcatalyzed Suzuki-Miyaura coupling of a chi oropyridi ne-N-oxide. (c) 2005 Elsevier Ltd. All rights reserved.