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

Base Information

• Chemical Name: 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene
• CAS No.: 54154-45-9
• Molecular Formula: C₁₉H₂₆O
• Molecular Weight: 270.415
• Mol file: 54154-45-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene 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: 92.0%

2-[(3S,4S)-3-(4-methoxyphenyl)-4-{2-[(triethylsilyl)oxy]propan-2-yl}cyclohexylidene]ethyl picolinate + methylmagnesium bromide (75-16-1) → 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene (54154-45-9)

Guidance literature:

methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; zinc(II) iodide; In tetrahydrofuran; at 0 ℃; for 0.5h;

2-[(3S,4S)-3-(4-methoxyphenyl)-4-{2-[(triethylsilyl)oxy]propan-2-yl}cyclohexylidene]ethyl picolinate; In tetrahydrofuran; at -78 ℃; for 1h; regioselective reaction;

DOI:10.1002/chem.201303538

Reference yield:

2-((1S,2S,4R)-2-(4-methoxyphenyl)-4-methyl-4-vinylcyclohexyl)propan-2-ol → 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene (54154-45-9)

Guidance literature:

With thionyl chloride; In pyridine; at -10 ℃; for 0.5h;

DOI:10.1016/j.tet.2015.02.092

Reference yield:

(1R,5R)-(+)-β-pinene (127-91-3,25719-60-2) → 1-methoxy-4-((1S,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene (54154-45-9)

Guidance literature:

Multi-step reaction with 10 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

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; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 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:

(S,E)-1-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-4-methoxybenzene

methylmagnesium bromide

(1R,5R)-(+)-β-pinene

nopinone

Downstream raw materials:

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

1-((1S,2R,5R)-2-Isopropyl-5-methyl-5-vinyl-cyclohexyl)-4-methoxy-benzene

1-((R)-2-Isopropyl-5-methyl-5-vinyl-cyclohex-1-enyl)-4-methoxy-benzene