trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate | 1111644-44-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate
• 英文别名: ethyl (E)-5-hydroxy-5-methyl-4-oxohex-2-enoate
• CAS: 1111644-44-0
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: FALOVRRNJUMSAK-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  反-3-(2-呋喃基)丙烯醛 、 trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate 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40%的产率得到(1S,2R,3R,5R)-ethyl-2-(furan-2-yl)-5-(2-hydroxypropan-2-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
• 作为产物：
  描述：

  ethyl 2,5-dihydroxy-5-methyl-4-oxohexanoate 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到trans-ethyl-4-oxo-5-hydroxy-5-methylhex-2-enoate
  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.