3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one

Base Information

• Chemical Name: 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one
• CAS No.: 223103-66-0
• Molecular Formula: C₂₂H₂₆OS
• Molecular Weight: 338.514
• Mol file: 223103-66-0.mol

Synonyms:3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one

Chemical Property of 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one

There total 7 articles about 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one 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: 80.0%

3-Isobutoxy-1-(2-methyl-allyl)-6-((E)-4-phenylsulfanyl-hexa-3,5-dienyl)-cyclohex-2-enol → 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one (223103-66-0)

Guidance literature:

With lithium perchlorate; acetic acid; In ethyl acetate; at 0 ℃; for 2h;

DOI:10.1021/jo9824192

Reference yield: 13.0%

3-Isobutoxy-1-(2-methyl-allyl)-6-((E)-4-phenylsulfanyl-hexa-3,5-dienyl)-cyclohex-2-enol → 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one (223103-66-0) + 8bβ-(2-methyl-allyl)-8-phenylsulfanyl-2,2aβ,3,4,5aβ,6,8aα,8bβ-octahydro-1H-acenaphthylene-5-one + 5α-isobutoxy-10-methyl-8-phenylsulfanyl-2,2aβ,3,4,5aβ,6,8aα,8bβ-octahydro-1H-5β,8bβ-prop-9-enoacenaphthylene + 5α-isobutoxy-10-methyl-8-phenylsulfanyl-2,2aβ,3,4,5aβ,6,8aα,8bβ-octahydro-1H-5β,8bβ-prop-10-enoanoacenaphthylene + 5α-isobutoxy-10-methyl-8-phenylsulfanyl-2,2aβ,3,4,5aβ,6,8aα,8bβ-octahydro-1H-5β,8bβ-propanoanoacenaphthylen-10-ylidene

Guidance literature:

With lithium perchlorate; trifluoroacetic acid; In diethyl ether; at 0 ℃; for 1h; Product distribution; other catalysts, temperature; intramolecular cycloaddition;

DOI:10.1021/jo9824192

Reference yield:

3-isobutoxycyclohex-2-en-1-one (23074-59-1) → 3-(3-methyl-allyl)-4-(4-phenylsulfanyl-hexa-3(E),5-dienyl)-2-cyclohexen-1-one (223103-66-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 10 h

2: 99 percent / TBAF / tetrahydrofuran / 0 - 20 °C

3: 1.) vinylmagnesium bromide, 2.) 1,1'-(azodicarbonyl)dipiperidine / 1.) THF, -78 deg C, 30 min, 2) THF, -78 deg C to 0 deg C, 3 h

4: 1.) 9-borabicyclo<3.3.1>nonane / 1.) THF, 35 deg C, 12 h, 2.) THF, 0 deg C, 3 h

5: 96 percent / TMEDA / tetrahydrofuran / 0.25 h / -78 °C

6: 80 percent / LiClO₄, glacial AcOH / ethyl acetate / 2 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 9-borabicyclo[3.3.1]nonane dimer; N,N,N,N,-tetramethylethylenediamine; vinyl magnesium bromide; tetrabutyl ammonium fluoride; lithium perchlorate; acetic acid; 1,1'-azodicarbonyl-dipiperidine; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo9824192

upstream raw materials:

3-isobutoxycyclohex-2-en-1-one

3-(4-isobutoxy-2-oxo-cyclohexen-3-enyl)-propionaldehyde

6-(3-hydroxy-propyl)-3-isobutoxy-2-cyclohexen-1-one

6-<3-(tert-butyldimethylsilyloxy)-propyl>-3-isobutoxy-2-cyclohexen-1-one