(1R,2S,4R)-1,2-epoxy-p-menthane-4-ol | 22555-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2S,4R)-1,2-epoxy-p-menthane-4-ol
• 英文别名: 1R,4S-terpinen-4-ol-epoxide；(1S,3S,6R)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptan-3-ol；(1S,3S,6R)-6-methyl-3-propan-2-yl-7-oxabicyclo[4.1.0]heptan-3-ol
• CAS: 22555-56-2
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: JLNJUKBAHGGNLB-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R)-1,2-epoxy-p-menthane-4-ol 在 硫酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 2(S)-Hydroxy-1(S),4(R)-cineol
  参考文献：
  名称：

  Stereospecific Transformation of Terpinen-4-ol to Dihydropinol

  摘要：

  A simple transformation of terpinen-4-ol (1) to dihydropinol (4) is described. S-Terpinen-4-ol was stereospecifically oxidized with vanadyl diacac to cis-terpinen-4-ol-epoxide (2). Reduction with LiAlD4 afforded the unexpected 1R-deutero-2S,4S-dihydroxy menthane (3) which was cyclized in acid to 4.

  DOI：

  10.1080/00397919608004590
• 作为产物：
  描述：

  (+)-4-萜品醇 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 三乙胺 作用下， 以 甲苯 为溶剂， 以85%的产率得到(1R,2S,4R)-1,2-epoxy-p-menthane-4-ol
  参考文献：
  名称：

  Stereospecific Transformation of Terpinen-4-ol to Dihydropinol

  摘要：

  A simple transformation of terpinen-4-ol (1) to dihydropinol (4) is described. S-Terpinen-4-ol was stereospecifically oxidized with vanadyl diacac to cis-terpinen-4-ol-epoxide (2). Reduction with LiAlD4 afforded the unexpected 1R-deutero-2S,4S-dihydroxy menthane (3) which was cyclized in acid to 4.

  DOI：

  10.1080/00397919608004590

文献信息

• Sustainable catalytic protocols for the solvent free epoxidation and <i>anti</i>-dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H₂O₂ as oxidant
  作者：William B. Cunningham、Joshua D. Tibbetts、Marc Hutchby、Katarzyna A. Maltby、Matthew G. Davidson、Ulrich Hintermair、Pawel Plucinski、Steven D. Bull

  DOI：10.1039/c9gc03208h

  日期：——

  tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to

  使用含水H 2 O 2的钨基多金属氧酸盐催化剂作为一种良性氧化剂，作为一种良性氧化剂，已用于多种生物可再生萜烯底物的三取代烯烃键的无溶剂催化环氧化。该环氧化方案已经按比例放大以产生以克为单位的氧化柠檬烯，3-氧化烯和α-pine烯，并且催化剂被循环使用三次以生成3-氧化烯。萜烯底物的反应性较低的二取代烯烃键的环氧化可通过在50°C下进行催化环氧化反应来实现。已经开发出能够使未处理的粗硫酸盐松节油直接环氧化以提供3-氧化烯，α-pine烯氧化物和β-pine烯氧化物的方法。用非均相酸催化剂（Amberlyst-15）处理粗环氧产品（无需后处理）可得到纯净的环氧化合物水解，得到相应的萜烯-抗二醇类，收率高。
• Stereoselective trans-dihydroxylation of terpinen-4-ol: synthesis of some stereoisomers of p-menthane-1,2,4-triol
  作者：Ioan Cristea、Erika Kozma、Carmen Batiu

  DOI：10.1016/s0957-4166(02)00207-0

  日期：2002.6

  A high level of trans-stereoselectivity in the dihydroxylation of the homoallylic alcohol, terpinen-4-ol 1 (R=H) has been achieved. Thus, the enantiomeric triols 2a and 2b were separately synthesized in high yield and with high stereoselectivity by trans-dihydroxylation of the enantiomeric (4S)-terpinen-4-ol 1a (R = H), and (4R)-terpinen-4-ol 1b (R=H), respectively, using hydrogen peroxide as oxidant and V2O5; as catalyst. In the same way, the enantiomeric triols 3a and 3b were obtained from the enantiomeric (4S)-terpinen-4-yl tosylate 1a (R=tosyl) and (4R)-terpinen-4-yl tosylate 1b (R=tosyl), respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.