4a(2H)-Naphthalenemethanol,5-ethenyl-1,3,4,7,8,8a-hexahydro-1,1-dimethyl-,(4aS,8aR)-(9CI)

Base Information

Chemical Name:4a(2H)-Naphthalenemethanol,5-ethenyl-1,3,4,7,8,8a-hexahydro-1,1-dimethyl-,(4aS,8aR)-(9CI)
CAS No.:796047-24-0
Molecular Formula:C₁₅H₂₄O
Molecular Weight:220.355
Hs Code.:
Mol file:796047-24-0.mol

Synonyms:4a(2H)-Naphthalenemethanol,5-ethenyl-1,3,4,7,8,8a-hexahydro-1,1-dimethyl-,(4aS,8aR)-(9CI)

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Chemical Property of 4a(2H)-Naphthalenemethanol,5-ethenyl-1,3,4,7,8,8a-hexahydro-1,1-dimethyl-,(4aS,8aR)-(9CI)

Chemical Property:

PSA：20.23000
LogP:3.69760

Purity/Quality:

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Technology Process of 4a(2H)-Naphthalenemethanol,5-ethenyl-1,3,4,7,8,8a-hexahydro-1,1-dimethyl-,(4aS,8aR)-(9CI)

There total 5 articles about 4a(2H)-Naphthalenemethanol,5-ethenyl-1,3,4,7,8,8a-hexahydro-1,1-dimethyl-,(4aS,8aR)-(9CI) 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: 98.0%

: tert-butyl-(1,1-dimethyl-5-vinyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-ylmethoxy)-dimethyl-silane

: 796047-24-0
((4aS,8aR)-1,1-Dimethyl-5-vinyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-yl)-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2004.08.161

Reference yield:

: 219861-72-0
4a-(<oxy>methyl)-5-methoxy-1-methyl-4,4a,7,8-tetrahydro-2(3H)-naphthalenone

: 796047-24-0
((4aS,8aR)-1,1-Dimethyl-5-vinyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-yl)-methanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Li; t-BuOH / liquid ammonia / -78 °C

1.2: NaBH₄ / methanol / 0 °C

2.1: NaH; CS₂; HMPA / imidazole / Heating

2.2: MeI

2.3: 94 percent / n-Bu₃SnH; AIBN / xylene / Heating

3.1: tetrahydrofuran / 0 °C

3.2: BaSO₄; H₂; quinoline / Pd / methanol

4.1: 75 percent / CuSO₄ / xylene / Heating

5.1: 98 percent / TBAF / tetrahydrofuran

With carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; lithium; sodium hydride; copper(II) sulfate; tert-butyl alcohol; 1H-imidazole; In tetrahydrofuran; ammonia; xylene; 2.1: Barton-McCombie radical deoxygenation;
DOI:10.1016/j.tetlet.2004.08.161

Reference yield:

: (2R,4aR,8aR)-4a-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methoxy-1,1-dimethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-ol

: 796047-24-0
((4aS,8aR)-1,1-Dimethyl-5-vinyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-yl)-methanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH; CS₂; HMPA / imidazole / Heating

1.2: MeI

1.3: 94 percent / n-Bu₃SnH; AIBN / xylene / Heating

2.1: tetrahydrofuran / 0 °C

2.2: BaSO₄; H₂; quinoline / Pd / methanol

3.1: 75 percent / CuSO₄ / xylene / Heating

4.1: 98 percent / TBAF / tetrahydrofuran

With carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; sodium hydride; copper(II) sulfate; 1H-imidazole; In tetrahydrofuran; xylene; 1.1: Barton-McCombie radical deoxygenation;
DOI:10.1016/j.tetlet.2004.08.161