2-(hydroxy-pyridin-3-yl-methyl)cyclohex-2-enone | 1013935-82-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxy-pyridin-3-yl-methyl)cyclohex-2-enone
• 英文别名: 2-[(S)-hydroxy(pyridin-3-yl)methyl]cyclohex-2-en-1-one
• CAS: 1013935-82-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: AGYPTVFKGLACPM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 2-环己烯-1-酮 在 三乙烯二胺 、 (R)-1,1'-(3,3'-bis(3,5-bis(trifluoromethyl)phenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diyl)-bis(3-(3,5-bis-trifluoromethyl)phenyl)thiourea 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 2-(hydroxy-pyridin-3-yl-methyl)cyclohex-2-enone 、 2-(hydroxy-pyridin-3-yl-methyl)cyclohex-2-enone
  参考文献：
  名称：

  Asymmetric Morita-Baylis-Hillman Reaction of Arylaldehydes with 2-Cyclohexen-1-one Catalyzed by Chiral Bis(Thio)urea and DABCO

  摘要：

  Novel bis(thio)urea organocatalysts were synthesized from axially chiral (R)-(-)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diamine (H-8-BINAM), and their catalytic abilities have been examined in the Morita-Baylis-Hillman reaction of 2-cyclohexen-1-one or 2-cyclopenten-1-one with a wide range of aromatic aldehydes in combination with DABCO. The best result was achieved in the reaction of 3-fluorobenzaldehyde with 2-cyclohexen-1-one to give the desired Morita-Baylis-Hillman product in 79% yield and 88% ee.

  DOI：

  10.1021/ol7028806