2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane

Base Information

• Chemical Name: 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane
• CAS No.: 54154-46-0
• Molecular Formula: C₁₉H₂₆O₂
• Molecular Weight: 286.414
• Mol file: 54154-46-0.mol

Synonyms:

Chemical Property of 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane

There total 13 articles about 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane 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:

1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene (54154-45-9) → 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane (54154-46-0)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 5 ℃; for 1h; Cooling with ice;

DOI:10.1002/chem.201303538

Reference yield:

2-[(3S,4S)-3-(4-methoxyphenyl)-4-{2-[(triethylsilyl)oxy]propan-2-yl}cyclohexylidene]ethyl picolinate → 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane (54154-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(I) bromide dimethylsulfide complex; zinc(II) iodide / tetrahydrofuran / 0.5 h / 0 °C

1.2: 1 h / -78 °C

2.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 5 °C / Cooling with ice

With copper(I) bromide dimethylsulfide complex; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.201303538

Reference yield:

(1R,5R)-(+)-β-pinene (127-91-3,25719-60-2) → 2-[(1S,2S,4R)-2-(4-Methoxy-phenyl)-4-methyl-4-vinyl-cyclohexyl]-2-methyl-oxirane (54154-46-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: rhodium(III) chloride hydrate; sodium periodate / tetrachloromethane; acetonitrile; water / 2 h / 20 °C

2.1: selenium(IV) oxide; sulfuric acid / methanol / 5 h / 20 °C / Cooling with ice

3.1: dihydrogen peroxide; pyridine / dichloromethane / 20 °C / Cooling with ice

4.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 2 h / -78 - -50 °C

5.1: boron trifluoride diethyl etherate / acetic anhydride / 20 °C / Cooling with ice

6.1: sodium hydride; methanol / mineral oil / 0.5 h / 20 °C

7.1: lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 0 °C

7.2: 20 °C

8.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 0.5 h / 20 °C

9.1: 2-chloro-1-methyl-pyridinium iodide; triethylamine; dmap / dichloromethane / 20 °C / Cooling with ice

10.1: copper(I) bromide dimethylsulfide complex; zinc(II) iodide / tetrahydrofuran / 0.5 h / 0 °C

10.2: 1 h / -78 °C

11.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 5 °C / Cooling with ice

With pyridine; methanol; dmap; selenium(IV) oxide; sodium periodate; copper(l) iodide; copper(I) bromide dimethylsulfide complex; rhodium(III) chloride hydrate; sulfuric acid; boron trifluoride diethyl etherate; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; zinc(II) iodide; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; acetic anhydride; acetonitrile; mineral oil;

DOI:10.1002/chem.201303538

upstream raw materials:

1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene

(1R,5R)-(+)-β-pinene

nopinone

(-)-Apoverbenone