(+)-(1S,3S,4R,8S)-p-menthane-3,9-diol | 167355-29-5

• 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: (+)-(1S,3S,4R,8S)-p-menthane-3,9-diol
• 英文别名: (+)-(βS,1R,2S,4S)-2-hydroxy-β,4-dimethylcyclohexaneethanol；(1S,2R,5S)-2-[(2S)-1-hydroxypropan-2-yl]-5-methylcyclohexan-1-ol
• CAS: 167355-29-5
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: BINZTUGHCIRHLP-JLIMGVALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (+)-(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
• 作为产物：
  描述：

  异胡薄荷醇 在 Pseudomonas cepacia lipase 、 甲基叔丁基醚 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (+)-(1S,3S,4R,8S)-p-menthane-3,9-diol
  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

• A method for the selective oxidation of 1,4-diols to lactols
  作者：E.J Corey、Anandan Palani

  DOI：10.1016/0040-4039(95)00571-s

  日期：1995.5

  Solutions of o-iodoxybenzoic acid in dimethyl sulfoxide at 23 °C effect the highly selective oxidation of a number of 1,4-bisprimary or 1,4-primary-secondary diols to γ-lactols, permitting a conversion which could not previously be accomplished in one step.

  在23°C下，邻碘氧基苯甲酸在二甲基亚砜中的溶液可将多种1,4-双伯或1,4-伯-仲二醇高度选择性地氧化为γ-内酯，从而实现了以前无法实现的转化一步。
• Asymmetric synthesis of dihydroartemisinic acid through intramolecular Stetter reaction
  作者：Rohan Kalyan Rej、Ranjan Kumar Acharyya、Samik Nanda

  DOI：10.1016/j.tet.2016.06.066

  日期：2016.8

  short and concise formal synthesis of enantiopure dihydroartemisinic acid from (R)-citronellal is described in this article. Intramolecular version of asymmetric Stetter reaction using Rovis aminoindane based NHC catalyst was explored to access the core substituted cyclohexanone framework which on functional group manipulation and late stage ring closing metathesis (RCM) reaction afforded an advanced intermediate

  本文描述了从（R）香茅醛中简短而简洁的形式合成对映体纯的二氢青蒿酸。探索了使用基于Rovis氨基茚满的NHC催化剂的分子内版本的不对称Stetter反应，以访问核心取代的环己酮骨架，该骨架在官能团操作和后期闭环复分解（RCM）反应的作用下提供了二氢青蒿酸的高级中间体。
• 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：——