5-Methoxy-3-[(Z)-10-pentadecen-1-yl]phenol

Base Information

• Chemical Name: 5-Methoxy-3-[(Z)-10-pentadecen-1-yl]phenol
• CAS No.: 137786-94-8
• Molecular Formula: C22H36O2
• Molecular Weight: 332.527
• Mol file: 137786-94-8.mol

Synonyms:Belamcandol B;

Chemical Property of 5-Methoxy-3-[(Z)-10-pentadecen-1-yl]phenol

Chemical Property:

• PSA: 29.46000
• LogP: 6.81050
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

BelamcandolB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Belamcandol B is a compound isolated from the seeds of B. Chinensis. and known to be an starting compound in the synthesis of 5-lipoxygenase inhibitors.

Technology Process of 5-Methoxy-3-[(Z)-10-pentadecen-1-yl]phenol

There total 8 articles about 5-Methoxy-3-[(Z)-10-pentadecen-1-yl]phenol 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%

1,3-dimethoxy-5-<(Z)-10'-pentadecenyl>benzene (34809-61-5) → belamcandol B (137786-94-8)

Guidance literature:

With sodium hydride; ethanethiol; In N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1248/cpb.41.561

Reference yield:

1-(tetrahydro-2-pyranyloxy)-9-decene (67136-13-4) → belamcandol B (137786-94-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) O₃, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, from -78 deg C to RT

2: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h

3: 91 percent / H₂ / 10percent Pd/C / ethanol / 12 h

4: 94 percent / p-toluenesulfonic acid, H₂O / tetrahydrofuran / 18 h / Ambient temperature

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

6: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h

7: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating

With n-butyllithium; oxalyl dichloride; potassium tert-butylate; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; ethanethiol; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.41.561

Reference yield:

9-((tetrahydro-2H-pyran-2-yl)oxy)nonan-1-al (70863-80-8) → belamcandol B (137786-94-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, hexane, RT, 15 min, 2.) THF, hexane, RT, 18 h

2: 91 percent / H₂ / 10percent Pd/C / ethanol / 12 h

3: 94 percent / p-toluenesulfonic acid, H₂O / tetrahydrofuran / 18 h / Ambient temperature

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

5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, 1 h

6: 91 percent / ethanethiol, NaH / dimethylformamide / 3 h / Heating

With n-butyllithium; oxalyl dichloride; potassium tert-butylate; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; ethanethiol; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.41.561

upstream raw materials:

1,3-dimethoxy-5-<(Z)-10'-pentadecenyl>benzene

1-(tetrahydro-2-pyranyloxy)-9-decene

9-((tetrahydro-2H-pyran-2-yl)oxy)nonan-1-al

9-Decen-1-ol

Downstream raw materials:

maesanin

dimethoxymaesanin

belamcandaphenol

1,4-dihydroxy-2-methoxy-6-<(Z)-10'-pentadecenyl>benzene

Refernces