(S)-(-)-1-(butanoyloxy)-2-cyclopentene | 151948-58-2

• 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: (S)-(-)-1-(butanoyloxy)-2-cyclopentene
• CAS: 151948-58-2
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: METLASQRHQWPFO-MRVPVSSYSA-N

物化性质

• 沸点：
  194.1±29.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-(butanoyloxy)-2-cyclopentene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 2-环戊烯-1-醇 、 (S)-(-)-2-cyclopentenol
  参考文献：
  名称：

  Substrate modification to increase the enantioselectivity of hydrolases. A route to optically-active cyclic allylic alcohols.

  摘要：

  The esterase-catalyzed resolution of the cyclic allylic acetates - 1-acetyloxy-2-cyclopentene, 1-acetyloxy-2-cyclohexene, and 1-acetyloxy-2-cycloheptene - was not enantioselective. We hypothesized that this inefficiency stems from the similarity in size of the substituents at the stereocenter (CH2-CH2 vs. CH=CH). To increase the enantioselectivity, we resolved precursors to these cyclic allylic alcohols: esters of trans-2-bromocycloalkanols (C5, C6, C7). These esters had a larger difference in the size of the substituents (CH2 vs. CHBr) at the stereocenter and were efficiently resolved by both cholesterol esterase and lipase from Pseudomonas cepacia (Amano P, PCL). A synthetic-scale resolution with PCL yielded the (1S,2S)-1-butanoyloxy-2-bromocycloalkanes in >98% ee. Heating with DBU to eliminate HBr, followed by reduction with LiAlH4 to cleave the ester, yielded the allylic alcohols: (S)-(-)-2-cyclopenten-1-ol (65% ee), (S)-(-)-2-cyclohexen-1-ol (>99% ee), and (S)-(-)-2-cyclohepten-1-ol (>98% ee).

  DOI：

  10.1016/s0957-4166(00)80126-3
• 作为产物：
  描述：

  trans-α-bromocyclopentanol butyrate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 10.0h， 以80%的产率得到(S)-(-)-1-(butanoyloxy)-2-cyclopentene
  参考文献：
  名称：

  Substrate modification to increase the enantioselectivity of hydrolases. A route to optically-active cyclic allylic alcohols.

  摘要：

  The esterase-catalyzed resolution of the cyclic allylic acetates - 1-acetyloxy-2-cyclopentene, 1-acetyloxy-2-cyclohexene, and 1-acetyloxy-2-cycloheptene - was not enantioselective. We hypothesized that this inefficiency stems from the similarity in size of the substituents at the stereocenter (CH2-CH2 vs. CH=CH). To increase the enantioselectivity, we resolved precursors to these cyclic allylic alcohols: esters of trans-2-bromocycloalkanols (C5, C6, C7). These esters had a larger difference in the size of the substituents (CH2 vs. CHBr) at the stereocenter and were efficiently resolved by both cholesterol esterase and lipase from Pseudomonas cepacia (Amano P, PCL). A synthetic-scale resolution with PCL yielded the (1S,2S)-1-butanoyloxy-2-bromocycloalkanes in >98% ee. Heating with DBU to eliminate HBr, followed by reduction with LiAlH4 to cleave the ester, yielded the allylic alcohols: (S)-(-)-2-cyclopenten-1-ol (65% ee), (S)-(-)-2-cyclohexen-1-ol (>99% ee), and (S)-(-)-2-cyclohepten-1-ol (>98% ee).

  DOI：

  10.1016/s0957-4166(00)80126-3