2-(1-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol

• 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-(1-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
• 英文别名: 2-hydroxy-β,4-dimethylcyclohexaneethanol；menthol；p-menthane-3,9-diol；9-Hydroxy-(-)-menthol
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: BINZTUGHCIRHLP-UHFFFAOYSA-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：

  2-(1-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol 在 N-甲基咪唑 、 2,2'-联吡啶 、 四(乙腈)三氟甲磺酸铜(I) 、 ABNO 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到Alpha,4-二甲基-2-羟基环己烷乙酸-Γ-内酯
  参考文献：
  名称：

  用于二醇的有氧氧化内酯化的高效和选择性 Cu/硝酰基催化方法

  摘要：

  Cu/硝酰基催化剂已被鉴定为在使用环境空气作为氧化剂的温和反应条件下促进二醇的高效和选择性有氧氧化内酯化。反应的化学选择性和区域选择性可以通过改变硝酰基助催化剂的特性来调节。Cu/ABNO 催化剂体系 (ABNO = 9-氮杂双环 [3.3.1]nonan-N-oxyl) 与对称二醇和受阻不对称二醇表现出优异的反应性，而 Cu/TEMPO 催化剂体系 (TEMPO = 2,2,6, 6-四甲基-1-哌啶基-N-氧基）对受阻较小的不对称二醇的氧化显示出优异的化学和区域选择性。这些催化剂体系与所有类型的醇（苄醇、烯丙基、脂肪醇）相容，介导 1,4-、1,5- 和一些 1,6-二醇的有效内酯化，并耐受不同的官能团，

  DOI：

  10.1021/jacs.5b01036
• 作为产物：
  描述：

  薄荷脑 在 双氧水 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 1.0h， 以95.64 g的产率得到2-(1-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
  参考文献：
  名称：

  [EN] HYDROBORATION-OXIDATION PROCESS
  [FR] PROCÉDÉ D'HYDROBORATION-OXYDATION

  摘要：

  本发明涉及有机合成领域，更具体地涉及通过化合物II的氢硼化-氧化反应制备化合物I的方法。

  公开号：

  WO2021175864A1

文献信息

• STEREOSELECTIVE SYNTHESIS OF PERHYDRO-3,6-DIALKYL-2-BENZO[B]FURANONES AND ANALOGS
  申请人：International Flavors & Fragrances Inc.

  公开号：US20200377466A1

  公开（公告）日：2020-12-03

  Synthetic methods of preparing perhydro-3,6-dimethyl-2-benzo[b]furanones, in particular dihydromintlactone, and analogs through reaction of dehydrogenation of menthanediols and analogs with a base in the presence of (carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II) as catalyst in good stereoselectivity and yields under stereochemistry controlled conditions are disclosed.

  本发明揭示了一种通过对蒎烷二醇及其类似物进行脱氢反应，与碱在(carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II)催化剂的存在下，以良好的立体选择性和产率控制条件下，合成过氢化3,6-二甲基-2-苯并[b]呋喃酮类化合物，特别是二氢薄荷内酯及其类似物的合成方法。
• STEREOSELECTIVE PREPARATION OF PERHYDRO-3,6-DIMETHYL-2-BENZO[B]FURANONES
  申请人：International Flavors & Fragrances Inc.

  公开号：EP3744717A1

  公开（公告）日：2020-12-02

  Synthetic methods and processes for preparation of perhydro-3,6-dimethyl-2-benzo[b]furanones, in particular dihydromintlactone, and analogs through reaction of dehydrogenation of menthanediols and analogs with a base in the presence of (carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II) as catalyst in good stereoselectivity and yields under stereochemistry controlled conditions are disclosed.

  本发明公开了在立体化学受控条件下，以羰基氯氢[双-(2-二苯基膦乙基)胺]钌(II)为催化剂，通过门冬烷二醇和类似物与碱的脱氢反应，制备全氢-3,6-二甲基-2-苯并[b]呋喃酮，特别是二氢薄荷内酯和类似物的合成方法和工艺，具有良好的立体选择性和收率。
• Stereoselective synthesis of perhydro-3,6-dialkyl-2-benzo[b]furanones and analogs
  申请人：International Flavors & Fragrances Inc.

  公开号：US10995080B2

  公开（公告）日：2021-05-04

  Synthetic methods of preparing perhydro-3,6-dimethyl-2-benzo[b]furanones, in particular dihydromintlactone, and analogs through reaction of dehydrogenation of menthanediols and analogs with a base in the presence of (carbonylchlorohydrido[bis-(2-diphenylphosphinoethyl)amine]ruthenium(II) as catalyst in good stereoselectivity and yields under stereochemistry controlled conditions are disclosed.

  本发明公开了在立体化学受控条件下，以羰基氯氢[双-(2-二苯基膦乙基)胺]钌(II)为催化剂，通过门冬烷二醇和类似物与碱的脱氢反应制备全氢-3,6-二甲基-2-苯并[b]呋喃酮，特别是二氢薄荷内酯和类似物的合成方法，具有良好的立体选择性和收率。
• 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.
• RIECHSTOFFALKOHOL FREISETZENDES POLYSILOXAN
  申请人：Evonik Degussa GmbH

  公开号：EP1888668A1

  公开（公告）日：2008-02-20