(1S,4R)-1-Hydroxy-2-oxolimonene

Base Information

• Chemical Name: (1S,4R)-1-Hydroxy-2-oxolimonene
• CAS No.: 24047-73-2
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• DSSTox Substance ID: DTXSID40332115
• Nikkaji Number: J1.121.167D
• Wikidata: Q27104438
• Metabolomics Workbench ID: 28130
• Mol file: 24047-73-2.mol

Synonyms:(1S,4R)-1-Hydroxy-2-oxolimonene;(1S,4R)-1-hydroxymenth-8-en-2-one;(1S,4R)-1-hydroxylimonen-2-one;24047-73-2;SCHEMBL2932755;CHEBI:38249;DTXSID40332115;LMPR0102090042;(1S,4R)-1-hydroxy-p-menth-8-en-2-one;Q27104438

Chemical Property of (1S,4R)-1-Hydroxy-2-oxolimonene

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=C)C1CCC(C(=O)C1)(C)O
• Isomeric SMILES: CC(=C)[C@@H]1CC[C@](C(=O)C1)(C)O

Technology Process of (1S,4R)-1-Hydroxy-2-oxolimonene

There total 1 articles about (1S,4R)-1-Hydroxy-2-oxolimonene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S,2S,4R)-limonene-1,2-diol (1946-00-5,13833-08-4,38630-75-0,39067-95-3,39903-99-6,39904-01-3,39904-04-6,39904-09-1,39904-12-6,57457-97-3,59121-74-3,59121-75-4,59121-76-5,59121-77-6,59121-82-3,76740-41-5) → (2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone (24047-73-2,7086-80-8)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; for 12h; Reflux;

DOI:10.1016/j.tetasy.2009.08.009

Reference yield: 99.0%

(2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone (24047-73-2,7086-80-8) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,5R)-2-((tert-butyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.08.009

Reference yield:

(2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone (24047-73-2,7086-80-8) → (1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol (1431536-56-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: -78 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

4.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ol400754e

upstream raw materials:

(1S,2S,4R)-limonene-1,2-diol

Downstream raw materials:

(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

(1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol