(-)-(1S,3S,4R,8S)-3-hydroxy-p-menthan-9-oic acid lactonediol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (-)-(1S,3S,4R,8S)-3-hydroxy-p-menthan-9-oic acid lactonediol
• 英文别名: (-)-(3S,3aR,6S,7aS)-hexahydro-3,6-dimethylbenzofuran-2(3H)-one；(3S,3aR,6S,7aS)-3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-3H-1-benzofuran-2-one
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: FGDINYRLQOKVQS-MAUMQABQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+)-(1S,3S,4R,8S)-p-menthane-3,9-diol 在 potassium permanganate 、 copper(II) sulfate 作用下， 反应 10.0h， 以55%的产率得到(-)-(1S,3S,4R,8S)-3-hydroxy-p-menthan-9-oic acid lactonediol
  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

• Sanghvi, Y. S.; Rao, A. S., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1377 - 1380
  作者：Sanghvi, Y. S.、Rao, A. S.

  DOI：——

  日期：——
• UTILISATION DE FURANONES A TITRE D'INGREDIENTS PARFUMANTS
  申请人：FIRMENICH SA

  公开号：EP0621892A1

  公开（公告）日：1994-11-02
• EP0621892B1
  申请人：——

  公开号：EP0621892B1

  公开（公告）日：1998-07-08
• [EN] USE OF FURANONES AS SCENTING INGREDIENTS<br/>[FR] UTILISATION DE FURANONES A TITRE D'INGREDIENTS PARFUMANTS
  申请人：——

  公开号：WO1994012143A2

  公开（公告）日：1994-06-09

  [EN] Furanones of formula (I), wherein R<1> and R<2> are the same and each represents a methyl radical, or R<1> and R<2> are different and each represents a hydrogen atom or a methyl radical, or else R<1> and R<2> together represent a methylene radical, are useful as scenting ingredients for the preparation of scenting compositions and scented articles in that they impart coumarin and balsamtype fragrances.
  [FR] Les furanones de formule (I) dans laquelle les symboles R1 et R2, pris séparément, sont identiques et représentent chacun un radical méthyle, ou sont différents et représentent chacun un atome d'hydrogène ou un radical méthyle, ou, pris ensemble, représentent un radical méthylène, sont utiles à titre d'ingrédients parfumants pour la préparation de compositions parfumantes et d'articles parfumés, auxquels elles confèrent des odeurs de type coumariné et balsamique.
• 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).