2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

Base Information

Chemical Name:2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone
CAS No.:1026602-48-1
Molecular Formula:C₃₁H₄₆O₃
Molecular Weight:466.704
Hs Code.:

Synonyms:2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

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Chemical Property of 2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

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Technology Process of 2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

There total 25 articles about 2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone 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:

: 38419-75-9
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

: 1026602-48-1
2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

Guidance literature:: Multi-step reaction with 16 steps

1.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C

2.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

2.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

3.1: 17 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

4.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating

5.1: 96 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 20 °C

6.1: 87 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

7.1: 98 percent / AlMe₃ / toluene; CH₂Cl₂ / 24 h / 0 - 20 °C

8.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -78 - -10 °C

9.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C

10.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C

11.1: 92 percent / NiCl₂*xH₂O; NaBH₄ / methanol / 3 h / 0 °C

12.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C

13.1: 198 mg / Na-Hg / methanol / 20 °C

14.1: 93 percent / TBAF / tetrahydrofuran / 48 h / Heating

15.1: 83 percent / Li-naphthalenide / tetrahydrofuran / 1 h / -78 °C

16.1: PhI(OAc)2 / 1,2-dichloro-ethane / 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; thionyl chloride; sodium amalgam; pyridine-SO₃ complex; [bis(acetoxy)iodo]benzene; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; lithium 1-naphthalenide; triethylamine; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo010154c

Reference yield:

: 564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5
(3aR)-(+)-sclareolide

: 1026602-48-1
2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

Guidance literature:: Multi-step reaction with 17 steps

1.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C

3.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

3.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

4.1: 17 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

5.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating

6.1: 96 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 20 °C

7.1: 87 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: 98 percent / AlMe₃ / toluene; CH₂Cl₂ / 24 h / 0 - 20 °C

9.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -78 - -10 °C

10.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C

11.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C

12.1: 92 percent / NiCl₂*xH₂O; NaBH₄ / methanol / 3 h / 0 °C

13.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C

14.1: 198 mg / Na-Hg / methanol / 20 °C

15.1: 93 percent / TBAF / tetrahydrofuran / 48 h / Heating

16.1: 83 percent / Li-naphthalenide / tetrahydrofuran / 1 h / -78 °C

17.1: PhI(OAc)2 / 1,2-dichloro-ethane / 1 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; thionyl chloride; sodium amalgam; pyridine-SO₃ complex; [bis(acetoxy)iodo]benzene; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; lithium 1-naphthalenide; triethylamine; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo010154c

Reference yield:

: 378197-91-2
(4aS,8aS,1R,2R)-1-(2-(tert-butyldiphenylsilyloxy)ethyl)-2,5,5,8a-tetramethylperhydro-2-naphthalenol

: 1026602-48-1
2-[(E)-(7R,8R)-8-Hydroxy-3,7-dimethyl-9-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-non-2-enyl]-[1,4]benzoquinone

Guidance literature:: Multi-step reaction with 15 steps

1.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

1.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

2.1: 17 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

3.1: 98 percent / TBAF / tetrahydrofuran / 1 h / Heating

4.1: 96 percent / Et₃N; SO₃*Py / dimethylsulfoxide / 1 h / 20 °C

5.1: 87 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: 98 percent / AlMe₃ / toluene; CH₂Cl₂ / 24 h / 0 - 20 °C

7.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / -78 - -10 °C

8.1: 99 percent / DIBALH / tetrahydrofuran / 0.5 h / -78 °C

9.1: 70 percent / NaH / tetrahydrofuran / 2 h / 20 °C

10.1: 92 percent / NiCl₂*xH₂O; NaBH₄ / methanol / 3 h / 0 °C

11.1: 76 percent / LDA / tetrahydrofuran / 4 h / -78 - 0 °C

12.1: 198 mg / Na-Hg / methanol / 20 °C

13.1: 93 percent / TBAF / tetrahydrofuran / 48 h / Heating

14.1: 83 percent / Li-naphthalenide / tetrahydrofuran / 1 h / -78 °C

15.1: PhI(OAc)2 / 1,2-dichloro-ethane / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; thionyl chloride; sodium amalgam; pyridine-SO₃ complex; [bis(acetoxy)iodo]benzene; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; lithium 1-naphthalenide; triethylamine; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene;
DOI:10.1021/jo010154c