4-benzyloxy-2-(4-methyl-thiazol-2-yl)-1-(5,6,7,9-tetrahydro-pyrido[3,4-c]azepin-8-yl)-penta-2,4-dien-1-one | 216012-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 4-benzyloxy-2-(4-methyl-thiazol-2-yl)-1-(5,6,7,9-tetrahydro-pyrido[3,4-c]azepin-8-yl)-penta-2,4-dien-1-one
• 英文别名: 13-(4-Methyl-1,3-thiazol-2-yl)-15-phenylmethoxy-4,11-diazatricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,13-pentaen-12-one
• CAS: 216012-32-7
• 化学式: C₂₄H₂₁N₃O₂S
• 分子量: 415.516
• InChiKey: BFDXEPYHXFAUJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-2-(4-methyl-thiazol-2-yl)-1-(5,6,7,9-tetrahydro-pyrido[3,4-c]azepin-8-yl)-penta-2,4-dien-1-one 在 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 作用下， 以 吡啶 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 15-(2-Methoxyphenyl)-13-(4-methyl-1,3-thiazol-2-yl)-4,11-diazatricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,13-pentaen-12-one
  参考文献：
  名称：

  Synthesis of tricyclic pyridones by radical cyclization

  摘要：

  A general and novel route for the synthesis of tricyclic pyridones by 5-, 6- and 7-exo-trig radical cyclization is described. The use of Pd-catalyzed cross-coupling reactions to introduce functionality at the 5-position of a pyridone is also presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00652-8
• 作为产物：
  描述：

  苄氧基乙醛二乙基乙缩醛 在 盐酸 、 偶氮二异丁腈 、 五氯化磷 、 三正丁基氢锡 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 23.0h， 生成 4-benzyloxy-2-(4-methyl-thiazol-2-yl)-1-(5,6,7,9-tetrahydro-pyrido[3,4-c]azepin-8-yl)-penta-2,4-dien-1-one
  参考文献：
  名称：

  Synthesis of tricyclic pyridones by radical cyclization

  摘要：

  A general and novel route for the synthesis of tricyclic pyridones by 5-, 6- and 7-exo-trig radical cyclization is described. The use of Pd-catalyzed cross-coupling reactions to introduce functionality at the 5-position of a pyridone is also presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00652-8

文献信息

• Tricyclic pyridones as functionally selective human GABAAα2/3 receptor-ion channel ligands
  作者：James Crawforth、John R. Atack、Susan M. Cook、Karl R. Gibson、Alan Nadin、Andrew P. Owens、Andrew Pike、Michael Rowley、Alison J. Smith、Bindi Sohal、Francine Sternfeld、Keith Wafford、Leslie J. Street

  DOI：10.1016/j.bmcl.2004.01.057

  日期：2004.4

  A series of tricyclic pyridones has been evaluated as benzodiazepine site ligands with functional selectivity for the alpha(3) over the alpha(1) containing subtype of the human GABA(A) receptor ion channel. This investigation led to the identification of a high affinity, functionally selective, orally bioavailable benzodiazepine site ligand that demonstrated activity in rodent anxiolysis models and reduced sedation relative to diazepam. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of tricyclic pyridones by radical cyclization
  作者：Alan Nadin、Timothy Harrison

  DOI：10.1016/s0040-4039(99)00652-8

  日期：1999.5

  A general and novel route for the synthesis of tricyclic pyridones by 5-, 6- and 7-exo-trig radical cyclization is described. The use of Pd-catalyzed cross-coupling reactions to introduce functionality at the 5-position of a pyridone is also presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.