Malabaricone A

Base Information

• Chemical Name: Malabaricone A
• CAS No.: 63335-23-9
• Molecular Formula: C21H26O3
• Molecular Weight: 326.436
• NSC Number: 287966
• DSSTox Substance ID: DTXSID70314727
• Nikkaji Number: J19.528F
• Wikidata: Q82067019
• Pharos Ligand ID: ADTXYYHPZ71L
• Metabolomics Workbench ID: 123023
• ChEMBL ID: CHEMBL1254269
• Mol file: 63335-23-9.mol

Synonyms:malabaricone A

Chemical Property of Malabaricone A

Chemical Property:

• Vapor Pressure: 3.75E-10mmHg at 25°C
• Melting Point: 80-82 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 488.1°Cat760mmHg
• PKA: 7.48±0.35(Predicted)
• Flash Point: 263.1°C
• PSA: 57.53000
• Density: 1.11g/cm³
• LogP: 5.25390
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 326.18819469
• Heavy Atom Count: 24
• Complexity: 339

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

MalabariconeA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCCCCCCCC(=O)C2=C(C=CC=C2O)O

Technology Process of Malabaricone A

There total 13 articles about Malabaricone A 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: 89.0%

(E)-1-(2-Benzyloxy-6-hydroxyphenyl)-9-phenyl-2-nonen-1-one (133839-74-4) → 1-(2',6'-dihydroxyphenyl)-9-phenylnonan-1-one (63335-23-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetone; for 6h; under 2574.3 Torr; Ambient temperature;

DOI:10.1248/cpb.39.18

Reference yield: 68.0%

3-Hydroxy-2-(9-phenyl-nonanoyl)-cyclohex-2-enone (134071-05-9) → 1-(2',6'-dihydroxyphenyl)-9-phenylnonan-1-one (63335-23-9)

Guidance literature:

With mercury(II) diacetate; sodium acetate; In acetic acid; at 120 - 125 ℃; 2-3 h;

DOI:10.1055/s-1990-27107

Reference yield:

1-bromo-6-benzyloxyhexane (54247-27-7) → 1-(2',6'-dihydroxyphenyl)-9-phenylnonan-1-one (63335-23-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / 2 h / 140 °C

2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min

3: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature

4: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min

5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min

6: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating

7: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; potassium tert-butylate; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In ethanol; acetone; benzene;

DOI:10.1248/cpb.39.18

upstream raw materials:

3-Hydroxy-2-(9-phenyl-nonanoyl)-cyclohex-2-enone

(E)-1-(2-Benzyloxy-6-hydroxyphenyl)-9-phenyl-2-nonen-1-one

1-(2,6-Dimethoxybenzoyl)-8-phenyloctane

7-phenylheptanoic acid

Refernces

• 1、 Oliver,Wilzer,Waters. "Synthesis of 1-(2,6-Dihydroxyphenyl)-1-alkanones and benzophenone by aromatization of 2-acyl-3-hydroxy-2-cyclohexene-1-ones with mercuric acetate". . p. 1117 - 1119. Retrieved 2007/10/02.