9-Tert-butyl-1-chloro-7-trimethylsilylchromeno[3,4-c]pyridin-5-one | 1448842-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9-Tert-butyl-1-chloro-7-trimethylsilylchromeno[3,4-c]pyridin-5-one
• 英文别名: 9-tert-butyl-1-chloro-7-trimethylsilylchromeno[3,4-c]pyridin-5-one
• CAS: 1448842-20-3
• 化学式: C₁₉H₂₂ClNO₂Si
• 分子量: 359.928
• InChiKey: XVGKKBGMPHUMKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  (4-叔-丁基苯基) N,N-二乙基氨基甲酸酯 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 20.67h， 生成 9-Tert-butyl-1-chloro-7-trimethylsilylchromeno[3,4-c]pyridin-5-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.