9-Oxa-4-azatetracyclo[8.8.0.02,7.011,16]octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one | 1448842-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 9-Oxa-4-azatetracyclo[8.8.0.02,7.011,16]octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one
• 英文别名: 9-oxa-4-azatetracyclo[8.8.0.02,7.011,16]octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one
• CAS: 1448842-28-1
• 化学式: C₁₆H₉NO₂
• 分子量: 247.253
• InChiKey: YVQBIYDSIRTCNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-naphthyl N,N-diethylcarbamate 在 盐酸 、 四(三苯基膦)钯 、 四甲基乙二胺 、 仲丁基锂 、 sodium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 34.5h， 生成 、 9-Oxa-4-azatetracyclo[8.8.0.02,7.011,16]octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one
  参考文献：
  名称：

  Combined Directed Metalation – Suzuki-Miyaura Cross Coupling Strategies. Synthesis of Isomeric Chromenopyridinones and Related Annulated Analogues

  摘要：

  A general strategy encompassing a Directed ortho Metalation (DoM) - Suzuki-Miyaura cross coupling and Directed remote Metalation (DreM) sequence for the synthesis of 5H-chromeno[4,3-c]pyridin-5-ones 5a-j, 5H-chromeno[3,4-b]pyridin-5-ones 6a-j, 5H-chromeno[3,4-c]pyridin-5-ones 13a-d, 12H-benzo[7,8]chromenopyridin-12-ones 16a-c, 17a-c, and pyrido[31,41:4,5]pyrano[2,3-e]indazol-5(111)-one analogues 18, 28 is reported. Thus, using the powerful directed metalation group properties of aryl O-carbamates 9a-h, 14a-c metalation-boronation followed by Suzuki-Miyaura coupling with 3-bromopyridine affords a variety of azabiaryls 7a-i, 8a-b, 12a-c, 15a-c which, upon DreM reaction leads to several series of chromenopyridinones 5a-j, 6a-j, 13a-d and pyridonaphthopyrones 16a-c, 17a-c. The synthesis of an unusual pyridopyranoindazolone 18 is also described.

  DOI：

  10.3987/com-12-s(n)131

文献信息

• Combined Directed Metalation – Suzuki-Miyaura Cross Coupling Strategies. Synthesis of Isomeric Chromenopyridinones and Related Annulated Analogues
  作者：Victor Snieckus、Ricarda E. Miller、Roman Sommer、Hope Fan、Ulrich Groth

  DOI：10.3987/com-12-s(n)131

  日期：——

  A general strategy encompassing a Directed ortho Metalation (DoM) - Suzuki-Miyaura cross coupling and Directed remote Metalation (DreM) sequence for the synthesis of 5H-chromeno[4,3-c]pyridin-5-ones 5a-j, 5H-chromeno[3,4-b]pyridin-5-ones 6a-j, 5H-chromeno[3,4-c]pyridin-5-ones 13a-d, 12H-benzo[7,8]chromenopyridin-12-ones 16a-c, 17a-c, and pyrido[31,41:4,5]pyrano[2,3-e]indazol-5(111)-one analogues 18, 28 is reported. Thus, using the powerful directed metalation group properties of aryl O-carbamates 9a-h, 14a-c metalation-boronation followed by Suzuki-Miyaura coupling with 3-bromopyridine affords a variety of azabiaryls 7a-i, 8a-b, 12a-c, 15a-c which, upon DreM reaction leads to several series of chromenopyridinones 5a-j, 6a-j, 13a-d and pyridonaphthopyrones 16a-c, 17a-c. The synthesis of an unusual pyridopyranoindazolone 18 is also described.