Debromolaurinterol

Base Information

• Chemical Name: Debromolaurinterol
• CAS No.: 10539-88-5
• Molecular Formula: C15H20O
• Molecular Weight: 216.323
• DSSTox Substance ID: DTXSID401316129
• Nikkaji Number: J13.420A
• Wikidata: Q27135166
• Metabolomics Workbench ID: 64628
• Mol file: 10539-88-5.mol

Synonyms:Debromolaurinterol;10539-88-5;2-[(1S,2R,5R)-1,2-Dimethylbicyclo[3.1.0]hex-2-yl]-5-methylphenol;CHEBI:66556;DTXSID401316129;Phenol, 2-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]hex-2-yl]-5-methyl-;Q27135166;2-[(1R,4R,5S)-4,5-dimethyl-4-bicyclo[3.1.0]hexanyl]-5-methyl-phenol;2-[(1S,2R,5R)-1,2-dimethyl-2-bicyclo[3.1.0]hexanyl]-5-methylphenol

Chemical Property of Debromolaurinterol

Chemical Property:

• PSA: 20.23000
• LogP: 3.77830
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 216.151415257
• Heavy Atom Count: 16
• Complexity: 300

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)C2(CCC3C2(C3)C)C)O
• Isomeric SMILES: CC1=CC(=C(C=C1)[C@@]2(CC[C@H]3[C@@]2(C3)C)C)O

Technology Process of Debromolaurinterol

There total 14 articles about Debromolaurinterol 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:

6-iodo-3-methyl-phenol (35928-80-4) → debromo-laurinterol (10539-88-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 4-dimethylaminopyridine / benzene / 4 h / Ambient temperature

2: Pd(OAc)2, (o-Tol)3P, Bu₃N / dimethylformamide / 12 h / 120 °C

3: H₂ / Pd/C / ethanol / 12 h / Ambient temperature

4: 92 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

5: 86 percent / K₂CO₃ / acetonitrile / 8 h / Heating

6: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h 2.) -78 deg C -> 0 deg C, 20 min

7: 57 percent / methanol / 4 h / Heating

8: t-BuOK / 2-methyl-propan-2-ol / Heating; influence of various bases, solvents, temperature and reaction time on yield

9: H₂ / Pd/C / ethanol / 12 h / Ambient temperature

With dmap; palladium diacetate; lithium aluminium tetrahydride; oxalyl dichloride; tributyl-amine; potassium tert-butylate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1998.485

Reference yield:

1,2-dimethylcyclopent-2-ene carboxylic acid (84884-01-5) → debromo-laurinterol (10539-88-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) (+)-dehydroabiethylamine

2: Et₃N / tetrahydrofuran / 0.25 h / Ambient temperature

3: 4-dimethylaminopyridine / benzene / 4 h / Ambient temperature

4: Pd(OAc)2, (o-Tol)3P, Bu₃N / dimethylformamide / 12 h / 120 °C

5: H₂ / Pd/C / ethanol / 12 h / Ambient temperature

6: 92 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

7: 86 percent / K₂CO₃ / acetonitrile / 8 h / Heating

8: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h 2.) -78 deg C -> 0 deg C, 20 min

9: 57 percent / methanol / 4 h / Heating

10: t-BuOK / 2-methyl-propan-2-ol / Heating; influence of various bases, solvents, temperature and reaction time on yield

11: H₂ / Pd/C / ethanol / 12 h / Ambient temperature

With dmap; palladium diacetate; lithium aluminium tetrahydride; oxalyl dichloride; tributyl-amine; leelamine; potassium tert-butylate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1998.485

Reference yield:

(S)-1,2-Dimethyl-cyclopent-2-enecarboxylic acid (210559-93-6) → debromo-laurinterol (10539-88-5)

Guidance literature:

Multi-step reaction with 10 steps

1: Et₃N / tetrahydrofuran / 0.25 h / Ambient temperature

2: 4-dimethylaminopyridine / benzene / 4 h / Ambient temperature

3: Pd(OAc)2, (o-Tol)3P, Bu₃N / dimethylformamide / 12 h / 120 °C

4: H₂ / Pd/C / ethanol / 12 h / Ambient temperature

5: 92 percent / LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

6: 86 percent / K₂CO₃ / acetonitrile / 8 h / Heating

7: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h 2.) -78 deg C -> 0 deg C, 20 min

8: 57 percent / methanol / 4 h / Heating

9: t-BuOK / 2-methyl-propan-2-ol / Heating; influence of various bases, solvents, temperature and reaction time on yield

10: H₂ / Pd/C / ethanol / 12 h / Ambient temperature

With dmap; palladium diacetate; lithium aluminium tetrahydride; oxalyl dichloride; tributyl-amine; potassium tert-butylate; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; tris-(o-tolyl)phosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1246/cl.1998.485

upstream raw materials:

laurinterol

(1S,2R,5R)-2-(2-Benzyloxy-4-methyl-phenyl)-1,2-dimethyl-bicyclo[3.1.0]hexane

6-iodo-3-methyl-phenol

1,2-dimethylcyclopent-2-ene carboxylic acid

Downstream raw materials:

2-Methoxy-4-methyl-1-(1,2,3-trimethyl-cyclopent-2-enyl)-benzene

2-Methoxy-4-methyl-1-(4,5,5-trimethyl-cyclopent-1-enyl)-benzene

laurinterol acetate

(1S,2R,5R)-2-(2-Methoxy-4-methyl-phenyl)-1,2-dimethyl-bicyclo[3.1.0]hexane

Refernces