5-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]-1α-(4-methyl-3-pentenyl)-1,4aβ,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene

Base Information

Chemical Name:5-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]-1α-(4-methyl-3-pentenyl)-1,4aβ,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene
CAS No.:122934-76-3
Molecular Formula:C₂₅H₄₂O₂
Molecular Weight:374.607
Hs Code.:
Mol file:122934-76-3.mol

Synonyms:

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Chemical Property of 5-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]-1α-(4-methyl-3-pentenyl)-1,4aβ,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene

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Technology Process of 5-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]-1α-(4-methyl-3-pentenyl)-1,4aβ,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene

There total 21 articles about 5-[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl]-1α-(4-methyl-3-pentenyl)-1,4aβ,6-trimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalene 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: 86.0%

: 122934-75-2
4-<(1ξ,2ξ,4aS,5S,8aS)-(+)-Decahydro-1-hydroxy-2,5,8a-trimethyl-5-(4-methylpent-3-enyl)naphthalen-1-yl>butan-2-one Ethylene Acetal

: 122934-76-3
4-<(4aS,5S,8aS)-(+)-3,4,4a,5,6,7,8,8a-Octahydro-2,5,8a-trimethyl-5-(4-methylpent-3-enyl)naphthalen-1-yl>butan-2-one Ethylene Acetal

Guidance literature:: With pyridine; thionyl chloride; at 0 ℃; for 0.833333h;

Reference yield: 86.0%

: (2R,4aS,5S,8aS)-2,5,8a-Trimethyl-1-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-5-(4-methyl-pent-3-enyl)-decahydro-naphthalen-1-ol

: 122934-76-3
4-<(4aS,5S,8aS)-(+)-3,4,4a,5,6,7,8,8a-Octahydro-2,5,8a-trimethyl-5-(4-methylpent-3-enyl)naphthalen-1-yl>butan-2-one Ethylene Acetal

Guidance literature:: With pyridine; thionyl chloride; at 0 ℃;
DOI:10.1039/c39880000815

Reference yield:

: 41722-49-0
(S)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione

: 122934-76-3
4-<(4aS,5S,8aS)-(+)-3,4,4a,5,6,7,8,8a-Octahydro-2,5,8a-trimethyl-5-(4-methylpent-3-enyl)naphthalen-1-yl>butan-2-one Ethylene Acetal

Guidance literature:: Multi-step reaction with 14 steps

1: 89 percent / D-camphorsulphonic acid (D-CSA), ethylene glycol / 45 °C

2: 1.) liq. NH₃, Li, H₂O / 1.) THF, reflux, 50 min; 2.) THF, r.t., overnight

3: 100 percent / LiAlH₄ / diethyl ether / a) -45 deg C, 1 h, b) r.t., 1.5 h

4: 1.) BuLi / 1.) THF, hexane, 0 deg C, 30 min; 2.) 0 deg C, 30 min

5: Bu₃SnH, azobisisobutyronitrile (AIBN) / xylene / 150 °C

6: 1.) BH₃-THF; 2.) aq. NaOH, 30percent H₂O₂ / 1.) THF, a) 0 deg C, 20 min, b) r.t., 20 min; 2.) H₂O, a) 0 deg C, 20 min, b) r.t., 20 min

7: 1.) (COCl)2, DMSO; 2.) Et₃N / 1.) CH₂Cl₂, -65 to -43 deg C, 30 min; 2.) 1 h

8: 1.) BuLi / 1.) Et₂O, hexane, r.t., 30 min, 2.) Et₂O, r.t., 3 h

9: 99 percent / pyridinium toluene-p-sulphonate (PPTS) / acetone; H₂O / 4 h / Heating

10: 87 percent / 60percent NaH / tetrahydrofuran / 16 h / Ambient temperature

11: 1.) NaH / 1.) THF, r.t., 50 min; 2.) r.t., overnight

12: 72 percent / LiCl / hexamethylphosphoric acid triamide / 2 h / 130 °C

13: 1.) Mg, 1,2-dibromoethane / 1.) THF, ultrasonic irradiation, 5 min; 2.) reflux, 2 h

14: 86 percent / SOCl₂, pyridine / 0.83 h / 0 °C

With pyridine; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; borane-THF; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonia; water; dihydrogen peroxide; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; lithium; sodium hydride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; lithium chloride; D-camphorsulphonic acid (D-CSA); ethylene glycol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; acetone; xylene;