(6R,7S,9R)-7-hydroxy-γ-dihydroionol | 908297-93-8

• 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: (6R,7S,9R)-7-hydroxy-γ-dihydroionol
• 英文别名: (1S,3R)-1-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]butane-1,3-diol
• CAS: 908297-93-8
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: KGVONLLQOAAEQZ-GRYCIOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6R,7S,9R)-7-hydroxy-γ-dihydroionol 在 吡啶 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 (R)-(-)-γ-damascone
  参考文献：
  名称：

  Synthesis of the enantiomeric forms of α- and γ-damascone starting from commercial racemic α-ionone

  摘要：

  A straightforward synthesis of both enantiomers of alpha- and gamma-damascone is described. The title compounds were prepared by a divergent pathway starting from the enantiomeric forms of (6RS,7SR,9RS)-7-hydroxy-7,8-dihydro-alpha-ionol and of (6RS,7SR,9RS)-7hydroxy-7.8-dihydro-gamma-ionol. These building blocks were obtained from racemic alpha-ionone in four and five steps, respectively. The 7-hydroxy group was introduced by regio- and diastereoselective epoxidation of the conjugated double bond followed by reductive opening of the oxirane ring. The hydroxy-ketone obtained was reduced diastereo selectively to trans-alpha-diol that could be converted to the trans-gamma-diol by photochemical isomerization. Both diols were then resolved by lipase-mediated acetylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.024
• 作为产物：
  描述：

  Acetic acid (1S,3R)-3-acetoxy-1-((R)-2,2-dimethyl-6-methylene-cyclohexyl)-butyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 (6R,7S,9R)-7-hydroxy-γ-dihydroionol
  参考文献：
  名称：

  Synthesis of the enantiomeric forms of α- and γ-damascone starting from commercial racemic α-ionone

  摘要：

  A straightforward synthesis of both enantiomers of alpha- and gamma-damascone is described. The title compounds were prepared by a divergent pathway starting from the enantiomeric forms of (6RS,7SR,9RS)-7-hydroxy-7,8-dihydro-alpha-ionol and of (6RS,7SR,9RS)-7hydroxy-7.8-dihydro-gamma-ionol. These building blocks were obtained from racemic alpha-ionone in four and five steps, respectively. The 7-hydroxy group was introduced by regio- and diastereoselective epoxidation of the conjugated double bond followed by reductive opening of the oxirane ring. The hydroxy-ketone obtained was reduced diastereo selectively to trans-alpha-diol that could be converted to the trans-gamma-diol by photochemical isomerization. Both diols were then resolved by lipase-mediated acetylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.05.024

文献信息

• Synthesis of the enantiomeric forms of α- and γ-damascone starting from commercial racemic α-ionone
  作者：Stefano Serra、Claudio Fuganti

  DOI：10.1016/j.tetasy.2006.05.024

  日期：2006.6

  A straightforward synthesis of both enantiomers of alpha- and gamma-damascone is described. The title compounds were prepared by a divergent pathway starting from the enantiomeric forms of (6RS,7SR,9RS)-7-hydroxy-7,8-dihydro-alpha-ionol and of (6RS,7SR,9RS)-7hydroxy-7.8-dihydro-gamma-ionol. These building blocks were obtained from racemic alpha-ionone in four and five steps, respectively. The 7-hydroxy group was introduced by regio- and diastereoselective epoxidation of the conjugated double bond followed by reductive opening of the oxirane ring. The hydroxy-ketone obtained was reduced diastereo selectively to trans-alpha-diol that could be converted to the trans-gamma-diol by photochemical isomerization. Both diols were then resolved by lipase-mediated acetylation. (c) 2006 Elsevier Ltd. All rights reserved.