(+)-(1R,4S)-4-Hydroxy-Δ⁸-p-menthen-3-on | 35736-67-5

• 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: (+)-(1R,4S)-4-Hydroxy-Δ⁸-p-menthen-3-on
• 英文别名: 5-ref-Methyl-2-trans-hydroxy-2-isopropenyl-cyclohexanon；(2S,5R)-2-hydroxy-5-methyl-2-prop-1-en-2-ylcyclohexan-1-one
• CAS: 35736-67-5
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: AALYQEIWIWMEAJ-SCZZXKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  cis R-(+)-pulegone oxide 在 对甲苯磺酸 作用下， 生成 (+)-(1R,4S)-4-Hydroxy-Δ⁸-p-menthen-3-on
  参考文献：
  名称：

  （-）-顺式-薄荷酚和（+）-普莱贡的染料敏化光氧合。用于添加的O- 2（1 Δ克）与烯丙基键双键。羟基或羰基†

  摘要：

  （-）-顺式-Pulegol（1）和（+）-pulegone（2）易于在溶液中进行染料敏化的光氧合时添加一摩尔的氧，几乎仅形成烯丙基氢过氧化物。

  DOI：

  10.1002/hlca.19710540714

文献信息

• Synthetic Chemistry with Fullerenes. Photooxygenation of Olefins
  作者：Hidetoshi Tokuyama、Eiichi Nakamura

  DOI：10.1021/jo00084a036

  日期：1994.3

  Under irradiation with visible or UV (>290 nm) light in the presence of molecular oxygen and a minute amount of fullerenes, olefins and dienes undergo ene and Diels-Alder reactions with singlet oxygen to give photooxygenation products. The regio- and stereoselectivities of the photooxygenation of beta-myrcene, (+)-pulegone, 4-methylpent-3-en-2-ol, and (+)-limonene were very similar to those observed in known singlet oxygen reactions, indicating that the fullerene-sensitized reaction generates free singlet oxygen. The efficiency of fullerenes and conventional sensitizers was qualitatively examined by using the Diels-Alder reaction between O-1(2) and furan-2-carboxylic acid as a probe. Among those examined, C-70 was found to be the most effective. The reaction was the fastest and completed with as little as 0.0001 equiv of C-70. C-60 and hematoporphyrin were found to be of similar efficiency. The methanofullerene 13, which lacks one olefinic conjugation in the C-60 core, was as good as C60 itself, but the aminofullerene 14, lacking six double bonds, was quite inferior. The fullerene carboxylic acid 15, which was previously shown to show considerable biochemical activity, was found to be capable of generating singlet oxygen in aqueous DMSO.
• Thermal and acid-catalyzed reactions of pulegone oxide
  作者：William Reusch、Donald F. Anderson、Calvin Keith Johnson

  DOI：10.1021/ja01020a037

  日期：1968.8
• Farbstoffsensibilisierte Photo-Oxygenierung von(−)-<i>cis</i>-Pulegol und (+)-Pulegon. Zur Addition von O₂(¹Δ_g) an Doppelbindungen mit allylständiger. Hydroxyl- oder Carbonyl-Gruppe
  作者：K. H. Schulte-Elte、M. Gadola、B. L. Müller

  DOI：10.1002/hlca.19710540714

  日期：1971.11.1

  (−)-cis-Pulegol (1) and (+)-pulegone (2) readily add one mole of oxygen on dyesensitized photo-oxygenation in solution, forming almost exclusively allyl hydroperoxides.

  （-）-顺式-Pulegol（1）和（+）-pulegone（2）易于在溶液中进行染料敏化的光氧合时添加一摩尔的氧，几乎仅形成烯丙基氢过氧化物。