(1R,2R,3S)-diethyl 4-oxo-2-phenylcyclopentane-1,3-dicarboxylate | 1111644-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S)-diethyl 4-oxo-2-phenylcyclopentane-1,3-dicarboxylate
• CAS: 1111644-92-8
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: UKIDVUMHDDBGMO-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (1R,2R,3S,4R)-diethyl-4-hydroxy-4-(2-hydroxypropan-2-yl)-2-phenylcyclopentane-1,3-dicarboxylate 在 高碘酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以85%的产率得到(1R,2R,3S)-diethyl 4-oxo-2-phenylcyclopentane-1,3-dicarboxylate
  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