(S)-(+)-5-acetoxy-2-cyclopentenone | 737806-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-(+)-5-acetoxy-2-cyclopentenone
• 英文别名: [(1S)-2-oxocyclopent-3-en-1-yl] acetate
• CAS: 737806-84-7
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: IAQZQUFZWSAUCE-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(+)-5-acetoxy-2-cyclopentenone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以100%的产率得到(S)-(+)-2-acetoxycyclopentanone
  参考文献：
  名称：

  Chemoenzymatic synthesis of α′- and α-acetoxylated cyclic ketones

  摘要：

  alpha,beta-Unsaturated and saturated cyclic ketones were selectively oxidized at the alpha'- and alpha-positions using Mn(OAc)(3) and Pb(OAc)(4), respectively, resulting in high chemical yields. The resultant racemic alpha'- and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha'- and alpha-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of alpha'-acetoxy-alpha,beta-unsaturated cyclic ketones were determined by transforming them into the corresponding saturated alpha-acetoxy cyclic ketones of known absolute configuration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.019
• 作为产物：
  描述：

  (2-oxocyclopent-3-en-1-yl) acetate 在 ammonium sulfate 、 phosphate buffer 、 pig liver esterase 作用下， 反应 5.0h， 以45%的产率得到(S)-(+)-5-acetoxy-2-cyclopentenone
  参考文献：
  名称：

  Chemoenzymatic synthesis of α′- and α-acetoxylated cyclic ketones

  摘要：

  alpha,beta-Unsaturated and saturated cyclic ketones were selectively oxidized at the alpha'- and alpha-positions using Mn(OAc)(3) and Pb(OAc)(4), respectively, resulting in high chemical yields. The resultant racemic alpha'- and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha'- and alpha-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of alpha'-acetoxy-alpha,beta-unsaturated cyclic ketones were determined by transforming them into the corresponding saturated alpha-acetoxy cyclic ketones of known absolute configuration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.019

文献信息

• Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives
  作者：Fazilet Devrim Özdemirhan、Murat Çelik、Selin Atlı、Cihangir Tanyeli

  DOI：10.1016/j.tetasy.2006.01.004

  日期：2006.1

  α′-acetoxy α,β-unsaturated cyclopentanone and cyclohexanone have been resolved into the corresponding enantiomerically enriched α′-hydroxylated and acetoxylated compounds with 96–97% ee via PLE hydrolysis. Stereoselectivity in the palladium(II)-catalyzed reaction between the enantiomerically enriched α′-acetoxylated compounds and diazomethane has been investigated. In the α′-acetoxylated cyclopentenone

  外消旋的α'-乙酰氧基α，β-不饱和环戊酮和环己酮已通过PLE水解分解为相应的对映体富集的具有96-97％ee的α'-羟基化和乙酰氧基化的化合物。研究了对映体富集的α'-乙酰氧基化化合物与重氮甲烷之间在钯（II）催化反应中的立体选择性。在α'-乙酰氧基化的环戊烯酮中，优先的环丙烷化反应以反形式发生，而α'-乙酰氧基化的环己烯酮提供顺式和反式产物（syn：anti，61：36％）。通过NOE实验确定产物的相对构型。