| 1619235-79-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• CAS: 1619235-79-8
• 化学式: C₂₂H₂₇N₃O₂
• 分子量: 365.475
• InChiKey: DHMZXFVTMIAAGL-CAQIIQHBSA-N

物化性质

• 沸点：
  560.7±50.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.12
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以71.429%的产率得到
  参考文献：
  名称：

  Synthesis of (−)-Pseudotabersonine, (−)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow

  摘要：

  Natural product modification with photo-redox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.

  DOI：

  10.1021/ja506170g
• 作为产物：
  描述：

  21α-cyano-16α-(methoxycarbonyl)cleavamine 在 [4,4′-di-tert-butyl-2,2′-bipyridine-κ²N¹,N^1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-pyridin-2-yl-κN]phenyl-κC¹}iridium(III) 、 palladium 10% on activated carbon 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.42h， 生成
  参考文献：
  名称：

  Synthesis of (−)-Pseudotabersonine, (−)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow

  摘要：

  Natural product modification with photo-redox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.

  DOI：

  10.1021/ja506170g