(+)-(3S,4S)-p-mentha-1,8(10)diene-3,9-diol 9-acetate | 477717-65-0

• 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,4S)-p-mentha-1,8(10)diene-3,9-diol 9-acetate
• 英文别名: (+)-(1S,2S)-2-hydroxy-4-methyl-β-methylenecyclohex-3-eneethanol α-acetate；2-[(1S,2S)-2-hydroxy-4-methylcyclohex-3-en-1-yl]prop-2-enyl acetate
• CAS: 477717-65-0
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: BNZVOQBRWCOGCH-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4S)-p-mentha-1,8(10)diene-3,9-diol 9-acetate 在 Rh(H)(PEt₃)₃ 盐酸 、 氢氧化钾 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 39.0h， 生成 (-)-(3S,4S)-3,9-epoxy-p-mentha-1,8(9)-diene
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9
• 作为产物：
  描述：

  1-乙酰氧基-3-甲基-1,3-丁二烯 在 Pseudomonas cepacia lipase 、 甲基叔丁基醚 作用下， 以 苯 为溶剂， 反应 18.0h， 生成 (+)-(3S,4S)-p-mentha-1,8(10)diene-3,9-diol 9-acetate
  参考文献：
  名称：

  Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers

  摘要：

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).

  DOI：

  10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9

文献信息

• Enzyme-Mediated Preparation of Enantiomerically Pure p-Menthan- 3,9-diols and Their Use for the Synthesis of Natural p-Menthane Lactones and Ethers
  作者：Stefano Serra、Claudio Fuganti

  DOI：10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9

  日期：2002.8

  The diasiereoselective preparation of the p-menthane-3,9-diols (+/-)-12, (+/-)-13a, (+/-)-13b, and (+/-)-18 and the study of their enzymic resolution is described (Scheme 1). The corresponding enantiomer-enriched diols obtained by means of the lipase-mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p-menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e., of the enantiomeric form of 3-hydroxy-p-menthan-9-oic acid lactone 1, of mintlactone 2, of the 3,9-epoxy-p-menth-1,8(10)-diene 10, and of the pheromone vesperal 11 (Schemes 2 and 3).