1,4-epidioxy-p-menth-2-one (1R,4S,6R) | 114612-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1,4-epidioxy-p-menth-2-one (1R,4S,6R)
• 英文别名: trans-(3R,6S)-epidioxy-p-menthene；(+)-(1R,4S,7R)-7-isopropyl-5-methyl-2,3-dioxabicyclo[2.2.2]oct-5-ene；(3R,4R)-3,6-epidioxy-p-menth-1-ene；(3R,4R)-3,6-Epidioxy-p-menth-1-en；(1R,4S,7R)-5-methyl-7-propan-2-yl-2,3-dioxabicyclo[2.2.2]oct-5-ene
• CAS: 114612-55-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: PAGUSKCEKZOQHZ-UTLUCORTSA-N

物化性质

• 沸点：
  189.9±20.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-epidioxy-p-menth-2-one (1R,4S,6R) 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以39%的产率得到(3R,4R,6S)-3,6-dihydroxymenth-1-ene
  参考文献：
  名称：

  Oxygenated bisabolanes from Alpinia densibracteata

  摘要：

  Seven novel oxygenated bisabolane sesquiterpenes and four oxygenated menthane monoterpenes have been isolated from the dichloromethane extract of Alpinia densibracteata in addition to known bisabolanes and menthanes. The structures of these compounds were established by NMR spectroscopy and by some chemical transformations. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0031-9422(96)00863-1
• 作为产物：
  描述：

  水芹烯 在 氧气 、 亚甲兰 、 异丙醇 作用下， 生成 1,4-epidioxy-p-menth-2-one (1R,4S,6R)
  参考文献：
  名称：

  Schenck et al., Justus Liebigs Annalen der Chemie, 1953, vol. 584, p. 125,149

  摘要：

  DOI：

文献信息

• Konkurrenz von Endoperoxid- und Hydroperoxid-Bildung bei der Umsetzung von Singulett-Sauerstoff mit cyclischen, konjugierten Dienen. Teil I
  作者：Rudolf Matusch、Gerhard Schmidt

  DOI：10.1002/hlca.19890720107

  日期：1989.2.1

  Competition of Endoperoxide and Hydroperoxide Formation in the Reaction of Singlet Oxygen with Cyclic, Conjugated Dienes

  单线态氧与环状共轭二烯反应中内过氧化物和氢过氧化物的竞争
• Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols
  作者：Peter Valente、Thomas D. Avery、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo8020506

  日期：2009.1.2

  1,4-Disubstituted 2,3-dioxabicyclo[2.2.2]oct-5-enes were dihydroxylated with osmium tetroxide to yield diols anti to the peroxide linkage in a highly selective manner. Reduction of the peroxide bond furnished cyclohexane-1,2,3,4-tetraols with toxocarol relative stereochemistry in excellent yield. This new methodology was employed to synthesize the natural product (1S,2R,3S,4R,5R)-2-methyl-5-(propa

  用四氧化将1，4-二取代的2，3-二氧杂双环[2.2.2]辛-5-烯二羟基化，以高度选择性的方式产生抗过氧化物键合的二醇。过氧化物键的还原提供了具有相对产率的甲苯甲酚相对立体化学的环己烷-1,2,3,4-四醇。该新方法用于合成天然产物（1 S，2 R，3 S，4 R，5 R）-2-甲基-5-（丙-2-基）环己烷-1,2,3,4- （R的短序列中的tetrol（1））-α-水芹烯。此外，在研究2,3-二氧杂双环[2.2.2]辛烷-5,6-二醇的化学过程中，发现了迄今未知的重排，其对于合成1,4-二羰基包括光学富集的合成子具有广泛的适用性。 。还报道了适用于这种重排的广泛的机械研究。
• Photo-oxidation of α-phellandrene: The formation of cyclohexadienyl hydroperoxides and their reduction to arene 1,4-hydrates
  作者：Robert Atkins、Howard A.J. Carless

  DOI：10.1016/s0040-4039(00)96872-2

  日期：1987.1

  Dye-sensitised photo-oxidation of α-phellandrene (3) yields, besides the expected endoperoxides, the cyclohexadienyl hydroperoxides (6) and (7); reduction of these latter gives the unstable arene 1,4-hydrates (9) and (10).

  α-水芹烯（3）的染料敏化光氧化除产生预期的内过氧化物外，还产生环己二烯基过氧化氢（6）和（7）。减少后者，得到不稳定的芳烃1,4-水合物（9）和（10）。
• Comparative analysis of three Australian finger lime (Citrus australasica) cultivars: Identification of unique citrus chemotypes and new volatile molecules
  作者：Estelle Delort、Alain Jaquier、Erik Decorzant、Christian Chapuis、Alessandro Casilli、Eric Frérot

  DOI：10.1016/j.phytochem.2014.10.023

  日期：2015.1

  The volatile constituents of the peel of three cultivars of Australian finger lime (Citrus australasica) were investigated: Alstonville, Judy's Everbearing and Durham's Emerald. Both qualitative and quantitative GC-MS analyses were performed on their peel solvent extract. The results showed that the unique phenotypes of finger lime are also correlated to unique molecular compositions. Each cultivar revealed a different chemotype: limonene/sabinene for cv. Alstonville, limonene/citronellal/isomenthone for cv. Judy's Everbearing, and limonene/citronellal/ citronellol for cv. Durham's Emerald. To the best of our knowledge, these chemotypes have never been reported in any other citrus species. Furthermore, the amounts of some volatile constituents (gamma-terpinene, alpha-pinene, beta-pinene, citral), which are generally the major constituents besides limonene in lime species, were surprisingly low in the three cultivars. Comparative GC-MS analysis also showed that some volatile molecules tended to be specific to one cultivar and could therefore be considered as markers. Moreover six molecules were reported for the first time in a citrus extract and confirmed by synthesis. Heart-cutting enantioselective two-dimensional GC-MS was performed to determine the enantiomeric distribution of the major chiral constituents. The combined data on three finger lime cultivars gives evidence of their divergence from other citrus species. (C) 2014 Elsevier Ltd. All rights reserved.
• Matusch, Rudolf; Schmidt, Gerhard, Angewandte Chemie, 1988, vol. 100, # 5, p. 729 - 730
  作者：Matusch, Rudolf、Schmidt, Gerhard

  DOI：——

  日期：——