(-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

Base Information

• Chemical Name: (-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone
• CAS No.: 252290-05-4
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.274
• Mol file: 252290-05-4.mol

Synonyms:(-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

Chemical Property of (-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone

There total 1 articles about (-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone 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: 60.0%

(4aS,5R)-3,4,4a,5,6,7-hexahydro-4a,5-dimethyl-2H-1-benzopyran-2-one (252290-09-8) + dimethyl methane phosphonate (756-79-6) → (-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone (252290-05-4) + 3-((1S,2R)-1,2-dimethyl-6-oxocyclohexyl)propionic acid (252290-08-7)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

(4aS,5R)-3,4,4a,5,6,7-hexahydro-4a,5-dimethyl-2H-1-benzopyran-2-one; In tetrahydrofuran; hexane; at -20 ℃; for 6h;

DOI:10.1021/jo034838r

Reference yield:

(-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone (252290-05-4) → Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-[2-((1R,4aS,5R,8aS)-4a,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethyl]-oxiranylmethyl ester

Guidance literature:

Multi-step reaction with 9 steps

1.1: LiBr; Ni(acac)2 / diethyl ether; toluene / 0.08 h / 0 °C

1.2: diethyl ether; toluene / 24 h / 20 °C

1.3: 72 percent / diethyl ether; toluene / 1.5 h / -20 - 20 °C

2.1: i-Pr₂EtN / CH₂Cl₂ / 4 h / 20 °C

3.1: 120 mg / DBU / tetrahydrofuran / 15 h / Heating

4.1: TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

4.2: KF / ethanol / 72 h / Heating

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

5.2: 79 percent / tetrahydrofuran; hexane / 16 h / Heating

6.1: 71 percent / CuCl; PdCl₂; oxygen / dimethylformamide; H₂O / 20 h / 45 °C

7.1: NaH / tetrahydrofuran / 2 h / 5 °C

7.2: tetrahydrofuran / 10 h / Heating

7.3: 22 mg / DIBALH / CH₂Cl₂; toluene / 0.75 h / -78 °C

8.1: 53 percent / D-(-)-diethyl tartrate; titanium(IV) isopropoxide; molecular sieves 4 Angstroem / tert-butyl hydroperoxide / CH₂Cl₂; decane / 20 h / -20 °C

9.1: DMAP / CH₂Cl₂ / 5 h / 20 °C

With titanium(IV) isopropylate; dmap; bis(acetylacetonate)nickel(II); n-butyllithium; diethyl (2S,3S)-tartrate; 4 A molecular sieve; oxygen; titanium tetrachloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; copper(l) chloride; lithium bromide; palladium dichloride; tert.-butylhydroperoxide; In tetrahydrofuran; diethyl ether; decane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: Sakurai reaction / 5.2: Wittig olefination / 6.1: Wacker reaction / 8.1: Sharpless asymmetric epoxidation;

DOI:10.1021/jo034838r

Reference yield:

(-)-(4aS,5R)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone (252290-05-4) → (1R,4aS,5R,8aS)-1-benzenesulfonylmethyl-2-methylene-4a,5,8a-trimethylperhydronaphthalene

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiBr; Ni(acac)2 / diethyl ether; toluene / 0.08 h / 0 °C

1.2: diethyl ether; toluene / 24 h / 20 °C

1.3: 72 percent / diethyl ether; toluene / 1.5 h / -20 - 20 °C

2.1: i-Pr₂EtN / CH₂Cl₂ / 4 h / 20 °C

3.1: 120 mg / DBU / tetrahydrofuran / 15 h / Heating

4.1: 67 percent / triethylamine / tetrahydrofuran / 24 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

5.2: 75 percent / tetrahydrofuran; hexane / 24 h / Heating

6.1: 98 percent / oxone(R) / methanol; H₂O / 16 h / 20 °C

With bis(acetylacetonate)nickel(II); n-butyllithium; oxone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; 5.2: Wittig olefination;

DOI:10.1021/jo034838r

upstream raw materials:

(4aS,5R)-3,4,4a,5,6,7-hexahydro-4a,5-dimethyl-2H-1-benzopyran-2-one

dimethyl methane phosphonate

Downstream raw materials:

(1S,4aS,5R,8aS)-1-phenylsulfanylmethyl-4a,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-one

(1R,4aS,5R,8aS)-2-methylene-1-phenylsulfanylmethyl-4a,5,8a-trimethylperhydronaphthalene

(1S,4aS,5R,8aS)-1-benzenesulfonylmethyl-4a,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-1H-naphthalen-2-one