(5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Base Information

Chemical Name:(5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
CAS No.:517916-38-0
Molecular Formula:C₁₄H₂₀O₂
Molecular Weight:220.312
Hs Code.:

Synonyms:(5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

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Chemical Property of (5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

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Technology Process of (5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

There total 1 articles about (5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone 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: 97.0%

: 78-85-3,25120-30-3
2-methylpropenal

: 2244-16-8,6485-40-1
(S)-p-mentha-6,8-dien-2-one

: 517916-38-0
(5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: (S)-p-mentha-6,8-dien-2-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

2-methylpropenal; In tetrahydrofuran; hexane; at -78 ℃; for 4h;

With acetic acid; In tetrahydrofuran; hexane; at -78 - 20 ℃;
DOI:10.1021/ol034052f

Reference yield: 70.0%

: 105-36-2
ethyl bromoacetate

: 517916-38-0
(5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

: 517916-39-1
[(R)-1-((1S,6S)-6-Isopropenyl-3-methyl-2-oxo-cyclohex-3-enyl)-2-methyl-allyloxy]-acetic acid ethyl ester

Guidance literature:: With 2,6-dimethylpyridine; silver(l) oxide; In N,N-dimethyl-formamide; at 4 ℃; for 168h;
DOI:10.1021/ol034052f

Reference yield:

: 517916-38-0
(5S,6S)-6-[(1R)-1-hydroxy-2-methylallyl]-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

: C₂₅H₃₂N₂O₅S

Guidance literature:: Multi-step reaction with 4 steps

1: 70 percent / silver(I) oxide; 2,6-lutidine / dimethylformamide / 168 h / 4 °C

2: 87 percent / potassium hexamethyldisilazide / toluene; diethyl ether / -78 °C

3: 75 percent / pyridinium chlorochromate; silica gel / CH₂Cl₂; toluene / 24 h / 20 °C

4: aq. ethanol / 0.67 h / Heating

With 2,6-dimethylpyridine; silica gel; potassium hexamethylsilazane; pyridinium chlorochromate; silver(l) oxide; In diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Williamson etherification;
DOI:10.1021/ol034052f