(S)-5-acetoxy-3-methoxycyclopent-2-en-1-one | 462094-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-acetoxy-3-methoxycyclopent-2-en-1-one
• 英文别名: [(1S)-4-methoxy-2-oxocyclopent-3-en-1-yl] acetate
• CAS: 462094-13-9
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: JLSSDDKIPWWYGS-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-acetoxy-3-methoxycyclopent-2-en-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 4-羟基-(4S)-2-环戊烯-1-酮
  参考文献：
  名称：

  A new and efficient chemoenzymatic access to both enantiomers of 4-hydroxycyclopent-2-en-1-one

  摘要：

  A chemoenzymatic synthesis of both enantiomers of pharmacologically interesting 4-hydroxycyclopent-2-en-1-one in three steps starting from 3-methoxycyclopent-2-en-1-one is described. Manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclopent-2-en-1-one in high enantiomeric excess. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00168-4
• 作为产物：
  描述：

  (+/-)-5-acetoxy-3-methoxycyclopent-2-en-1-one 在 Amano PS 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 反应 24.0h， 以45%的产率得到(R)-5-hydroxy-3-methoxycyclopent-2-en-1-one
  参考文献：
  名称：

  A new and efficient chemoenzymatic access to both enantiomers of 4-hydroxycyclopent-2-en-1-one

  摘要：

  A chemoenzymatic synthesis of both enantiomers of pharmacologically interesting 4-hydroxycyclopent-2-en-1-one in three steps starting from 3-methoxycyclopent-2-en-1-one is described. Manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha-acetoxy enone affords acetoxy enone 3 and hydroxy enone 4 with high enantiomeric excesses and in good yields. The reduction of the acetoxy and hydroxy enones furnished both enantiomers of 4-hydroxycyclopent-2-en-1-one in high enantiomeric excess. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00168-4