(1S,2R,3R,5R)-ethyl-5-(2-hydroxypropan-2-yl)-2-(naphthalen-1-yl)-7-oxo-6-oxabicyclo[3.2.0]heptane-3-carboxylate | 1111644-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2R,3R,5R)-ethyl-5-(2-hydroxypropan-2-yl)-2-(naphthalen-1-yl)-7-oxo-6-oxabicyclo[3.2.0]heptane-3-carboxylate
• 英文别名: ethyl (1S,2R,3R,5R)-5-(2-hydroxypropan-2-yl)-2-naphthalen-1-yl-7-oxo-6-oxabicyclo[3.2.0]heptane-3-carboxylate
• CAS: 1111644-62-2
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: FDPIWZRXLBWUDQ-OZQHCQBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate 、 3-[1]naphthyl-acrylaldehyde 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45%的产率得到(1S,2R,3R,5R)-ethyl-5-(2-hydroxypropan-2-yl)-2-(naphthalen-1-yl)-7-oxo-6-oxabicyclo[3.2.0]heptane-3-carboxylate
  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

文献信息

• Stereodivergency of Triazolium and Imidazolium-Derived NHCs for Catalytic, Enantioselective Cyclopentane Synthesis
  作者：Juthanat Kaeobamrung、Jeffrey W. Bode

  DOI：10.1021/ol802739d

  日期：2009.2.5

  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.