2,5-Cyclohexadien-1-one, 4-methyl-4-[2-[(1S,6R)-1-methyl-6-(1-methylethyl)-3-cyclohexen-1-yl]eth yl]-

Base Information

Chemical Name:2,5-Cyclohexadien-1-one, 4-methyl-4-[2-[(1S,6R)-1-methyl-6-(1-methylethyl)-3-cyclohexen-1-yl]eth yl]-
CAS No.:499797-46-5
Molecular Formula:C19H28O
Molecular Weight:272.431
Hs Code.:

Synonyms:

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Chemical Property of 2,5-Cyclohexadien-1-one, 4-methyl-4-[2-[(1S,6R)-1-methyl-6-(1-methylethyl)-3-cyclohexen-1-yl]eth yl]-

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Technology Process of 2,5-Cyclohexadien-1-one, 4-methyl-4-[2-[(1S,6R)-1-methyl-6-(1-methylethyl)-3-cyclohexen-1-yl]eth yl]-

There total 14 articles about 2,5-Cyclohexadien-1-one, 4-methyl-4-[2-[(1S,6R)-1-methyl-6-(1-methylethyl)-3-cyclohexen-1-yl]eth yl]- 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:

: 499797-48-7
(R)-7-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-5-methyl-heptan-2-ol

: 499797-46-5
4-[2-((1S,6R)-6-Isopropyl-1-methyl-cyclohex-3-enyl)-ethyl]-4-methyl-cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

4.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

5.1: 19 g / KOH / methanol / 5 h

6.1: LDA; PhSeBr / tetrahydrofuran / 1 h / -78 °C

6.2: m-CPBA / tetrahydrofuran / 1 h

7.1: 2.5 g / TBAF / tetrahydrofuran / 48 h / 50 °C

8.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

8.2: tetrahydrofuran; various solvent(s) / 0.5 h

8.3: 85 percent / HMPA / 24 h

9.1: 77 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

10.1: Bu₃SnH; AIBN / toluene / 6 h / Heating

10.2: 0.9 g / PCC; 3 Angstroem MS / CH₂Cl₂ / 0.5 h

With pyridine; potassium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); Phenylselenyl bromide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ol026820t

Reference yield:

: 80-57-9,1196-01-6
(-)-Verbenone

: 499797-46-5
4-[2-((1S,6R)-6-Isopropyl-1-methyl-cyclohex-3-enyl)-ethyl]-4-methyl-cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 15 steps

1.1: Mg; I₂ / tetrahydrofuran / 0.5 h

1.2: 80 percent / CuI / tetrahydrofuran / -50 - 20 °C

2.1: LiAlH₄ / diethyl ether / 0.25 h

3.1: 4.9 g / imidazole / dimethylformamide / 2.5 h

4.1: O₃ / CH₂Cl₂ / 4 h / -78 °C

5.1: 30.5 g / diethyl ether; tetrahydrofuran / 2 h / 0 °C

6.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

8.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

9.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

10.1: 19 g / KOH / methanol / 5 h

11.1: LDA; PhSeBr / tetrahydrofuran / 1 h / -78 °C

11.2: m-CPBA / tetrahydrofuran / 1 h

12.1: 2.5 g / TBAF / tetrahydrofuran / 48 h / 50 °C

13.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

13.2: tetrahydrofuran; various solvent(s) / 0.5 h

13.3: 85 percent / HMPA / 24 h

14.1: 77 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

15.1: Bu₃SnH; AIBN / toluene / 6 h / Heating

15.2: 0.9 g / PCC; 3 Angstroem MS / CH₂Cl₂ / 0.5 h

With pyridine; 1H-imidazole; potassium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); Phenylselenyl bromide; tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; ozone; magnesium; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 5.1: Grignard reaction;
DOI:10.1021/ol026820t

Reference yield:

: 455252-76-3
(1S,4S,5S)-4-((S)-3,7-Dimethyl-oct-6-enyl)-4,6,6-trimethyl-bicyclo[3.1.1]heptan-2-one

: 499797-46-5
4-[2-((1S,6R)-6-Isopropyl-1-methyl-cyclohex-3-enyl)-ethyl]-4-methyl-cyclohexa-2,5-dienone

Guidance literature:: Multi-step reaction with 14 steps

1.1: LiAlH₄ / diethyl ether / 0.25 h

2.1: 4.9 g / imidazole / dimethylformamide / 2.5 h

3.1: O₃ / CH₂Cl₂ / 4 h / -78 °C

4.1: 30.5 g / diethyl ether; tetrahydrofuran / 2 h / 0 °C

5.1: 93 percent / N-methylmorpholine N-oxide / RuCl₂(PPh₃)3 / acetone / 12 h

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

7.1: 92 percent / N-methylmorpholine N-oxide; OsO₄; pyridine / NaHCO₃ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 504000 h / 30 °C / pH 7

8.1: NaIO₄ / tetrahydrofuran / 4 h / 20 °C / pH 7

9.1: 19 g / KOH / methanol / 5 h

10.1: LDA; PhSeBr / tetrahydrofuran / 1 h / -78 °C

10.2: m-CPBA / tetrahydrofuran / 1 h

11.1: 2.5 g / TBAF / tetrahydrofuran / 48 h / 50 °C

12.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h

12.2: tetrahydrofuran; various solvent(s) / 0.5 h

12.3: 85 percent / HMPA / 24 h

13.1: 77 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

14.1: Bu₃SnH; AIBN / toluene / 6 h / Heating

14.2: 0.9 g / PCC; 3 Angstroem MS / CH₂Cl₂ / 0.5 h

With pyridine; 1H-imidazole; potassium hydroxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); Phenylselenyl bromide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; lithium diisopropyl amide; tris(triphenylphosphine)ruthenium(II) chloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 4.1: Grignard reaction;
DOI:10.1021/ol026820t