arenarone

Base Information

• Chemical Name: arenarone
• CAS No.: 199180-36-4
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• Mol file: 199180-36-4.mol

Synonyms:arenarone

Chemical Property of arenarone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of arenarone

There total 19 articles about arenarone 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: 91.0%

2-((1R,2S,4aR,8aS)-1,2,4a-Trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-phenol (475301-85-0) → arenarone (199180-36-4)

Guidance literature:

With salcomine; oxygen; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0040-4039(02)01627-1

Reference yield: 33.0%

(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene (199180-35-3) → arenarone (199180-36-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4039(97)10075-2

Reference yield:

(-)-(4aR)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione (113666-06-1) → arenarone (199180-36-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 89 percent / p-TsOH / benzene / Heating

2: NaOMe / methanol / Heating

3: AcOH / ethanol / 15 °C

4: 1.) SOCl₂, pyridine, 2.) DIBAL / 1.) CH₂Cl₂, 0 deg C, 2.) toluene, -78 deg C

5: 99 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

6: hydroquinone / 1,2-dichloro-benzene / 180 °C

7: H₂ / Pd/C / CH₂Cl₂

8: 98 percent / LiAlH₄ / tetrahydrofuran / 0 °C

9: n-Bu₃P / tetrahydrofuran / Ambient temperature

10: 30percent H₂O₂ / 0 °C

11: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C to 0 deg C

12: 1.) n-BuLi / 1.) Et₂O, -78 deg C, 2.) Et₂O, -78 deg C

13: 88 percent / pyridine / 0 °C

14: 85 percent / H₂ / 10percent Pd/C / methanol / 3800 Torr / Ambient temperature

15: 83 percent / Zn, TiCl₄ / tetrahydrofuran / Ambient temperature

16: 33 percent / CAN / acetonitrile; H₂O / Ambient temperature

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; ammonium cerium(IV) nitrate; tributylphosphine; hydrogen; dihydrogen peroxide; sodium methylate; titanium tetrachloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; acetic acid; hydroquinone; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-benzene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(97)10075-2

upstream raw materials:

(1R,2S,4aR,8aS)-1-(2,5-Dimethoxy-benzyl)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalene

2-((1R,2S,4aR,8aS)-1,2,4a-Trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-phenol

cis-decaline

(4aS,5R,6S,8aR)-5-(2-Methoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

Downstream raw materials:

(+)-arenarol