(3aS,5S,6R,6aS)-5-(4-bromophenyl)-3a-hydroxy-3,3-dimethyl-6-phenylhexahydro-1H-cyclopenta[c]furan-1-one | 1111644-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3aS,5S,6R,6aS)-5-(4-bromophenyl)-3a-hydroxy-3,3-dimethyl-6-phenylhexahydro-1H-cyclopenta[c]furan-1-one
• 英文别名: (3aS,5S,6R,6aS)-5-(4-bromophenyl)-3a-hydroxy-3,3-dimethyl-6-phenyl-4,5,6,6a-tetrahydrocyclopenta[c]furan-1-one
• CAS: 1111644-65-5
• 化学式: C₂₁H₂₁BrO₃
• 分子量: 401.3
• InChiKey: UGFXINZCARBPKR-IKVWTGGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-hydroxy-1-(4-bromophenyl)-4-methylpent-1-en-3-one 、 肉桂醛 在 (5aR,10bS)-5a,10b-dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 16.25h， 以50%的产率得到(3aS,5S,6R,6aS)-5-(4-bromophenyl)-3a-hydroxy-3,3-dimethyl-6-phenylhexahydro-1H-cyclopenta[c]furan-1-one
  参考文献：
  名称：

  Stereodivergency of Triazolium and Imidazolium-Derived NHCs for Catalytic, Enantioselective Cyclopentane Synthesis

  摘要：

  Chiral triazolium- and imidazolium-derived N-heterocyclic carbene catalysts promote the direct annulation of alpha,beta-unsaturated aldehydes and achiral alpha-hydroxy enones to afford cyclopentane-fused lactones with high enantioselectivity. Remarkably, otherwise structurally identical imidazolium and triazolium precatalysts afford different major products. These studies provide both an efficient entry to valuable chiral structures and a dramatic demonstration of stereodivergency of chiral imidazolium versus triazolium-derived N-heterocyclic carbene catalysts.

  DOI：

  10.1021/ol802739d