(3S,6R)-3-acetoxy-6-hydroxy-α-ionone | 1001910-94-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S,6R)-3-acetoxy-6-hydroxy-α-ionone
• 英文别名: [(1S,4R)-4-hydroxy-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-yl] acetate
• CAS: 1001910-94-6
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: UXHJJZZJMILEFT-WHIKILRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (3S,6R)-3-acetoxy-6-hydroxy-α-ionone 在 甲醇 、 氢氧化钾 作用下， 生成 (±)-(3E)-4-[1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
  参考文献：
  名称：

  Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-α-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone

  摘要：

  A straightforward synthesis of both enantiomers of cis- and trans-3-acetoxy-6-hydroxy-alpha-ionone is described. The title compounds are prepared by resolution of the diastereoisomerically pure racemic 3,6-dihydroxy-alpha-ionone isomers. The latter process is based on two steps. The first is the enantio- and regioselective lipase-mediated acetylation of diols to afford the corresponding 3-acetoxy-derivatives. The second is the fractional crystallization of the latter compounds that increase their enantiomeric purity. These building blocks were used for the synthesis of both enantiomeric forms of the natural norterpenoids dehydrovomifoliol 3 and 8,9-dehydrotheaspirone 5. The latter compound is a natural flavor and its odor properties were evaluated by professional perfumers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.014
• 作为产物：
  描述：

  乙酸乙烯酯 、 (±)-(3E)-4-[1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one 在 lipase of Pseudomonas cepacia 作用下， 以 various solvent(s) 为溶剂， 以20%的产率得到(3S,6R)-3-acetoxy-6-hydroxy-α-ionone
  参考文献：
  名称：

  Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-α-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone

  摘要：

  A straightforward synthesis of both enantiomers of cis- and trans-3-acetoxy-6-hydroxy-alpha-ionone is described. The title compounds are prepared by resolution of the diastereoisomerically pure racemic 3,6-dihydroxy-alpha-ionone isomers. The latter process is based on two steps. The first is the enantio- and regioselective lipase-mediated acetylation of diols to afford the corresponding 3-acetoxy-derivatives. The second is the fractional crystallization of the latter compounds that increase their enantiomeric purity. These building blocks were used for the synthesis of both enantiomeric forms of the natural norterpenoids dehydrovomifoliol 3 and 8,9-dehydrotheaspirone 5. The latter compound is a natural flavor and its odor properties were evaluated by professional perfumers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.014