[(4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl]methyl acetate

Base Information

• Chemical Name: [(4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl]methyl acetate
• CAS No.: 936001-98-8
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.273
• DSSTox Substance ID: DTXSID60558138
• Mol file: 936001-98-8.mol

Synonyms:936001-98-8;[(4R)-1-hydroxy-4-prop-1-en-2-ylcyclohex-2-en-1-yl]methyl acetate;[(4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl]methyl acetate;((4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl)methyl acetate;DTXSID60558138

Chemical Property of [(4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl]methyl acetate

Chemical Property:

• PSA: 46.53000
• LogP: 1.82290
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 210.125594432
• Heavy Atom Count: 15
• Complexity: 293

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of [(4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl]methyl acetate

There total 7 articles about [(4R)-1-Hydroxy-4-(prop-1-en-2-yl)cyclohex-2-en-1-yl]methyl acetate 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: 54.0%

→ [(1R,4R)-1-hydroxy-4-(prop-1-en-2-yl)cyclohex-2-enyl]methyl acetate (123806-59-7,936001-98-8)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; pyridine; at 65 ℃; Cooling with ice;

Reference yield: 53.0%

[(1R,2S,4S)-1-hydroxy-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexyl]methyl acetate (1605281-09-1) → [(1S,4S)-1-hydroxy-4-(prop-1-en-2-yl)cyclohex-2-enyl]methyl acetate (1605281-10-4,936001-98-8)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; pyridine; at 65 ℃; Cooling with ice;

Reference yield:

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol (190718-78-6) → [(1S,4S)-1-hydroxy-4-(prop-1-en-2-yl)cyclohex-2-enyl]methyl acetate (1605281-10-4,936001-98-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.17 h

1.2: 14 h

2.1: sodium tetrahydroborate / ethanol / 1 h / 20 °C

2.2: 65 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 25 °C / Inert atmosphere

4.1: pyridine / 20 °C / Cooling with ice; Inert atmosphere

5.1: dihydrogen peroxide / tetrahydrofuran; pyridine / 65 °C / Cooling with ice

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; dihydrogen peroxide; In tetrahydrofuran; pyridine; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

(-)-perillyl alcohol

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol

(S)-tert-butyldimethyl[(4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methoxy]silane

(1R,2S,4S)-1-[(tert-butyldimethylsilyloxy)methyl]-2-(phenylselanyl)-4-(prop-1-en-2-yl)cyclohexanol

Downstream raw materials:

2-[(1S,6S)-3-(acetoxymethyl)-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentylresorcinol

Refernces