rac-6-acetoxy-4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-6-acetoxy-4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-one
• 英文别名: (5-oxo-4,6,7,8-tetrahydro-1,3-benzodioxin-6-yl) acetate
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: XZLQCMDMMATLHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-6-acetoxy-4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-one 在 锂硼氢 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以86%的产率得到(-)-4-acetoxy-2-hydroxymethyl-2-cyclohex-2-en-1-one
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one starting from cyclohexane-1,3-dione is described. Cyclohexane-1,3-dione was converted into 4,6,7,8-tetrahydrobenzo[1,3]dioxin-5-one and then manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of cc-acetoxy enone afforded the acetoxy enone and hydroxy enone with high enantiomeric excesses and in good yields. The reduction of the acetoxy enones furnished both enantiomers of 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one in high enantiomeric excess. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.028
• 作为产物：
  描述：

  manganese triacetate 、 4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-one 以 溶剂黄146 、 苯 为溶剂， 以92%的产率得到rac-6-acetoxy-4,6,7,8-tetrahydro-5H-1,3-benzodioxin-5-one
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one

  摘要：

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one starting from cyclohexane-1,3-dione is described. Cyclohexane-1,3-dione was converted into 4,6,7,8-tetrahydrobenzo[1,3]dioxin-5-one and then manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of cc-acetoxy enone afforded the acetoxy enone and hydroxy enone with high enantiomeric excesses and in good yields. The reduction of the acetoxy enones furnished both enantiomers of 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one in high enantiomeric excess. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.07.028

文献信息

• Chemoenzymatic synthesis of both enantiomers of 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one
  作者：Ayhan S. Demir、Deniz Senocak

  DOI：10.1016/j.tetasy.2004.07.028

  日期：2004.9

  A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one starting from cyclohexane-1,3-dione is described. Cyclohexane-1,3-dione was converted into 4,6,7,8-tetrahydrobenzo[1,3]dioxin-5-one and then manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of cc-acetoxy enone afforded the acetoxy enone and hydroxy enone with high enantiomeric excesses and in good yields. The reduction of the acetoxy enones furnished both enantiomers of 4-acetoxy-2-hydroxymethyl-cyclohex-2-en-1-one in high enantiomeric excess. (C) 2004 Elsevier Ltd. All rights reserved.

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