(4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

Base Information

Chemical Name:(4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone
CAS No.:931103-82-1
Molecular Formula:C₁₉H₁₈O₄S
Molecular Weight:342.416
Hs Code.:

Synonyms:(4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

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Chemical Property of (4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

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Technology Process of (4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

There total 4 articles about (4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone 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: 66.0%

: 931103-73-0
(4R,SR)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfinyl)methyl]cyclohexa-2,5-dienone

: 931103-82-1
(4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

: 3-(3,4-epoxy-3-methylbut-1-ynyl)-4-hydroxy-4-[(p-tolylsulfonyl)methyl]-cyclohexa-2,5-dienone

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;
DOI:10.1002/chem.200601330

Reference yield:

: 6-bromo-4-hydroxy-5-(3-methyl-but-3-en-1-ynyl)-4-(toluene-4-sulfinylmethyl)-cyclohex-2-enone

: 931103-82-1
(4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 2 steps

1: 2.3 g / LiBr; Li₂CO₃ / dimethylformamide / 1 h / 100 °C

2: 66 percent / meta-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

With lithium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200601330

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 931103-82-1
(4R)-4-hydroxy-3-(3-methylbut-3-en-1-ynyl)-4-[(p-tolylsulfonyl)methyl]cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: hexane; tetrahydrofuran / 2 h / -78 °C

1.3: 76 percent / aq. oxalic acid / tetrahydrofuran / 2 h

2.1: 2.3 g / LiBr; Li₂CO₃ / dimethylformamide / 1 h / 100 °C

3.1: 66 percent / meta-chloroperbenzoic acid / CH₂Cl₂ / 0 °C

With n-butyllithium; lithium carbonate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/chem.200601330