2-[[(1S,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol

Base Information

• Chemical Name: 2-[[(1S,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol
• CAS No.: 87764-13-4
• Molecular Formula: C21H30O2
• Molecular Weight: 314.4617
• NSC Number: 613793
• DSSTox Substance ID: DTXSID10420038
• Wikidata: Q82231292
• Mol file: 87764-13-4.mol

Synonyms:arenarol

Chemical Property of 2-[[(1S,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol

Chemical Property:

• Vapor Pressure: 1.02E-08mmHg at 25°C
• Boiling Point: 450.1°Cat760mmHg
• Flash Point: 200.3°C
• PSA: 40.46000
• Density: 1.08g/cm³
• LogP: 5.43910
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 459

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C1(C)CC3=C(C=CC(=C3)O)O)CCCC2=C)C
• Isomeric SMILES: CC1CC[C@]2([C@@H]([C@@]1(C)CC3=C(C=CC(=C3)O)O)CCCC2=C)C

Technology Process of 2-[[(1S,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol

There total 35 articles about 2-[[(1S,4aS,8aR)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]benzene-1,4-diol 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: 82.0%

Arenarone (87764-16-7,106190-06-1,129445-46-1) → (+/-)-Arenarol (87764-13-4,106190-05-0,129443-87-4)

Guidance literature:

With sodium dithionite; In tetrahydrofuran; for 0.0833333h;

DOI:10.1021/jo00121a030

Reference yield: 76.0%

arenarone (199180-36-4) → (+)-arenarol (87764-13-4)

Guidance literature:

With sodium dithionite; In tetrahydrofuran; water; at 20 ℃;

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

Reference yield:

(-)-(4aR)-1,4a-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione (113666-06-1) → (+)-arenarol (87764-13-4)

Guidance literature:

Multi-step reaction with 17 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

17: 75 percent / Na₂S₂O₄ / tetrahydrofuran; H₂O / Ambient temperature

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; sodium dithionite; 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:

arenarone

cis-decaline

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

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

Downstream raw materials:

dimethyl arenarol

arenarol diacetate

Aureol

(+)-5-epi-aureol