(1S,3R,4S)-1-hydroxy isomenthol | 58342-65-7

• 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: (1S,3R,4S)-1-hydroxy isomenthol
• 英文别名: 1α-hydroxy-l-menthol；(-)-(1S,3R,4S)-1-hydroxymenthol；(1S,3R,4S)-1-methyl-4-propan-2-ylcyclohexane-1,3-diol
• CAS: 58342-65-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: IIZCEIWXLSJQFP-AEJSXWLSSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  274.2±8.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 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：

  (1S,3R,4S)-1-hydroxy isomenthol 、 乙酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 (1R,2S,5S)-5-hydroxy-2-isopropyl-5-methylcyclohexyl acetate
  参考文献：
  名称：

  Lytic Activity of l-Menthol Derivatives against the Snow Blight Disease Fungus, Micronectriella nivalis

  摘要：

  Lytic activity of l-menthol (1) derivatives [(-)-(1S,3R,4S,6S)-6-hydroxymenthol (2), (-)-(1S,3R,4S)-1-hydroxymenthol (3), and (+)-(1S,3R,4R,6S)-6,8-dihydroxymenthol (4)] against the snow blight disease fungus, Micronectriella nivalis was investigated. Compounds 2, 3, and 4 had 85.0, 63.9, and 81.9% lytic activity, respectively, at a concentration of 0.2 mg/mL. The activity of each of the three compounds increased in a dose-response manner. To study the structure-activity relationship, acetyl esters of 1-4 [(-)-menthyl acetate (1Ac), (-)-6-hydroxymenthyl diacetate (2Ac), (-)-1-hydroxymenthyl 3-monoacetate (3Ac), and (-)-6,8-dihydroxymenthyl 3,6-diacetate (4Ac)] were synthesized with yields of 80.2-99.8% and were also assayed. The acetyl esters of 1Ac, 2Ac, 3Ac, and 4Ac had 51.2, 91.5, 66.0, and 95.2% lytic activity, respectively, at a concentration of 0.2 mg/mL, and these compounds showed further high lytic activity compared with the alcohols of 1-4. These acetyl esters also showed higher lytic activity as their concentration was increased. Of particular interest is the fact that 2Ac and 4Ac both had higher lytic activity at 0.05-0.2 mg/mL compared with copper 8-hydroxyquinolate, a standard chemical widely used to control snow blight. This is the first report on lytic activity of I-menthol derivatives.

  DOI：

  10.1021/jf0210831
• 作为产物：
  描述：

  (1S,3R,4S)-1-hydroxy isopulegol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以98%的产率得到(1S,3R,4S)-1-hydroxy isomenthol
  参考文献：
  名称：

  1-羟基新异薄荷醇和1-羟基新异薄荷醇的对映选择性制备

  摘要：

  阿对映选择性过程为（1制备中所述- [R，3 - [R，4 - [R）-1-羟基异胡薄荷醇3和（1 - [R，3小号，4 - [R）-1-羟基neoisopulegol 4在从香叶醇开始4个步骤。其对映体（1小号，3小号，4小号）-1-羟基异胡薄荷醇5和（1 - [R，3小号，4 - [R）-1-羟基neoisopulegol 5类似地制备。这些化合物被转化为1-羟基新异薄荷醇7、8和1-羟基异薄荷醇9、10。这些化合物大多数具有感官特性。

  DOI：

  10.1016/s0957-4166(97)00222-x

文献信息

• Preparation of biologically active substances and animal and microbial metabolites from menthols, cineoles and kauranes
  作者：Yoshinori Asakawa、Reiko Matsuda、Motoo Tori、Toshihiro Hashimoto

  DOI：10.1016/0031-9422(88)83033-4

  日期：1988.1

  and their structures elucidated by NMR spectroscopy. Some hydroxylated menthols showed plant growth inhibitory and strong mosquito repellent activity. Among the hydroxylated cineoles, microbial and animal metabolites of cineoles were included. From ent-kauranes, a plant growth inhibitory diterpene alcohol, (−)-16α-hydroxy kaurane was obtained along with 16α-kauran-13α-ol.

  摘要 间氯过苯甲酸或干臭氧氧化了六种单萜类化合物 l-薄荷醇、l-乙酸薄荷酯、异薄荷醇、新薄荷醇、1,4-桉树脑和 1,8-桉树脑和一种双萜烃 ent-kaurene。得到各种羟基化产物及其核磁共振谱阐明的结构。一些羟基化薄荷醇显示出植物生长抑制和强烈的驱蚊活性。在羟基化桉树脑中，包括桉树脑的微生物和动物代谢物。从 ent-kaurane 中获得了植物生长抑制性二萜醇 (-)-16α-羟基 kaurane 以及 16α-kauran-13α-ol。
• Amine Organocatalysis of Remote, Chemoselective C(sp³)–H Hydroxylation
  作者：Philip L. Hahn、Jared M. Lowe、Yubo Xu、Kevin L. Burns、Michael K. Hilinski

  DOI：10.1021/acscatal.2c00392

  日期：2022.4.15

  simple catalytic strategy for achieving high yielding and highly selective remote hydroxylation of compounds bearing oxidation-sensitive functional groups such as alcohols, ethers, carbamates, and amides. By employing hexafluoroisopropanol as the solvent in the absence of water, a proposed hydrogen-bonding effect leads to, among other advantages, as high as ≥99:1 chemoselectivity for remote aliphatic

  我们介绍了一种使用仲胺作为催化剂的恶氮丙啶介导的 C-H 羟基化的有机催化方法。我们还展示了这种操作简单的催化策略在实现带有氧化敏感官能团（如醇、醚、氨基甲酸酯和酰胺）的化合物的高产率和高选择性远程羟基化方面的优势。通过在不存在水的情况下使用六氟异丙醇作为溶剂，所提出的氢键效应除其他优势外，对 2° 醇的远程脂肪族羟基化具有高达 ≥ 99:1 的化学选择性，这是一个未解决的合成挑战，通常复杂化大量的酒精氧化。反应机制的初步研究表明，氧氮丙啶盐作为活性氧化剂的形成和 C-H 氧化步骤通过协同插入或氢原子转移/自由基反弹以立体有择的方式进行。此外，初步结果表明位点选择性会受到胺催化剂结构的影响。
• Biotransformation of one monoterpene by sporulated surface cultures of<i>Aspergillus niger</i>and<i>Penicillium</i>sp.
  作者：Akbar Esmaeili、Shirin Sharafian、Shila Safaiyan、Shamsali Rezazadeh、Abdolhossein Rustaivan

  DOI：10.1080/14786410802547341

  日期：2009.7.20

  In this study, biotransformation of menthol by sporulated surface culture of Aspergillus niger and Penicillium sp. was studied. The main bioconversion product obtained from menthol of A. niger was cis-p-menthan-7-ol and the main products obtained by surface Penicillium sp. were limonene, p-cymene and -terpinene using sporulated surface culture. The pathways involved in the biotransformation of menthol by A. niger and Penicillium sp. to main products are also discussed.
• ASAKAWA, YOSHINORI;MATSUDA, REIKO;TORI, MOTOO;HASHIMOTO, TOSHIHIRO, PHYTOCHEMISTRY, 27,(1988) N 12, C. 3861-3869
  作者：ASAKAWA, YOSHINORI、MATSUDA, REIKO、TORI, MOTOO、HASHIMOTO, TOSHIHIRO

  DOI：——

  日期：——
• Enantioselective preparation of 1-hydroxy neoisopulegol and 1-hydroxy neoisomenthol
  作者：Abdellatif Fkyerat、Raffaele Tabacchi

  DOI：10.1016/s0957-4166(97)00222-x

  日期：1997.7

  steps starting from geraniol. Their enantiomers (1S,3S,4S)-1-hydroxy isopulegol 5 and (1R,3S,4R)-1-hydroxy neoisopulegol 5 were prepared analogously. These compounds were converted to 1-hydroxy neoisomenthol 7, 8 and 1-hydroxy isomenthol 9, 10. Most of these compounds possess an organoleptic property.

  阿对映选择性过程为（1制备中所述- [R，3 - [R，4 - [R）-1-羟基异胡薄荷醇3和（1 - [R，3小号，4 - [R）-1-羟基neoisopulegol 4在从香叶醇开始4个步骤。其对映体（1小号，3小号，4小号）-1-羟基异胡薄荷醇5和（1 - [R，3小号，4 - [R）-1-羟基neoisopulegol 5类似地制备。这些化合物被转化为1-羟基新异薄荷醇7、8和1-羟基异薄荷醇9、10。这些化合物大多数具有感官特性。