2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone | 623531-70-4

• 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: 2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone
• 英文别名: 9-hydroxy-p-menthan-3-one；2-(1-Hydroxypropan-2-yl)-5-methylcyclohexan-1-one
• CAS: 623531-70-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: OVVORYLZOZFTDP-UHFFFAOYSA-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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  2-(2-Benzyloxy-1-methyl-ethyl)-5-methyl-cyclohexanone 在 palladium on activated charcoal 氢气 作用下， 以 various solvent(s) 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 8.0h， 以90%的产率得到2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone
  参考文献：
  名称：

  Hydrogenation and Hydrogenolysis with Pd/C in Poly(Ethylene Glycol) (PEG): A Practical and Recyclable Medium

  摘要：

  研究发现，PEG（400）中的 Pd/C 是一种可重复使用的高效反应介质，可用于氢化和氢解反应。催化剂和 PEG 均可在四次运行中有效循环使用，且活性不会明显降低。

  DOI：

  10.1055/s-2003-45007

文献信息

• Novel Cyclic Oxygenated Compounds Having Cooling, Fragrance, and Flavor Properties, and Uses Thereof
  申请人：Selifonov Sergey

  公开号：US20070274928A1

  公开（公告）日：2007-11-29

  Compositions that include compounds capable of producing a cooling sensory effect such as certain hydroxy-ketones and hydroxy-aldehyde compounds, their cyclic semi-ketals and semiacetals, and other derivatives thereof. The compounds impart a refreshing and cooling sensation of long duration and high potency, and thus are useful in a variety of formulations, including consumer products such as mouth formulations, food and beverage products, tobacco and smoking articles, fragrances, toiletries, ointments, and the like.

  这段话的意思是：包括某些羟基酮和羟基醛化合物、它们的环状半酮和半缩醛以及其他衍生物在内的化合物，可以产生冷却感官效应的组合物。这些化合物具有长时间和高效的清爽和冷却感觉，因此在各种配方中非常有用，包括消费品如口腔制剂、食品和饮料制品、烟草和吸烟用品、香水、化妆品、药膏等。
• In Vivo Studies on the Metabolism of the Monoterpene Pulegone in Humans Using the Metabolism of Ingestion-Correlated Amounts (MICA) Approach:  Explanation for the Toxicity Differences between (<i>S</i>)-(−)- and (<i>R</i>)-(+)-Pulegone
  作者：Wolfgang Engel

  DOI：10.1021/jf034702u

  日期：2003.10.1

  The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and alpha,alpha,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans.
• Hydrogenation and Hydrogenolysis with Pd/C in Poly(Ethylene Glycol) (PEG): A Practical and Recyclable Medium
  作者：S. Chandrasekhar、T. Shyamsunder、G. Chandrashekar、Ch. Narsihmulu

  DOI：10.1055/s-2003-45007

  日期：——

  Pd/C in PEG (400) has been found to be an efficient ­reusable reaction medium for hydrogenation and hydrogenolysis. Both the catalyst and PEG were recycled efficiently over four runs without appreciable loss of activity.

  研究发现，PEG（400）中的 Pd/C 是一种可重复使用的高效反应介质，可用于氢化和氢解反应。催化剂和 PEG 均可在四次运行中有效循环使用，且活性不会明显降低。