Moracin C

Base Information

• Chemical Name: Moracin C
• CAS No.: 69120-06-5
• Molecular Formula: C19H18O4
• Molecular Weight: 310.35
• UNII: TGZ4GH2N64
• DSSTox Substance ID: DTXSID70219182
• Nikkaji Number: J46.689A
• Wikidata: Q72492675
• Pharos Ligand ID: XML16MJA1DUL
• Metabolomics Workbench ID: 45979
• ChEMBL ID: CHEMBL2018876
• Mol file: 69120-06-5.mol

Synonyms:moracin C;moracin N

Chemical Property of Moracin C

Chemical Property:

• Vapor Pressure: 2.47E-08mmHg at 25°C
• Boiling Point: 439.4°Cat760mmHg
• PKA: 9.08±0.40(Predicted)
• Flash Point: 219.6°C
• PSA: 73.83000
• Density: 1.278g/cm³
• LogP: 4.72530
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 310.12050905
• Heavy Atom Count: 23
• Complexity: 419

Purity/Quality:

99%, ^*data from raw suppliers

MoracinC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=C(C=C1O)C2=CC3=C(O2)C=C(C=C3)O)O)C
• Uses: Moracin C is used as a diabetic medication and also used in other drug development. An inhibitor of Staphylococcus aureus enoyl-acyl carrier protein reductase from Morus alba leaf.

Technology Process of Moracin C

There total 41 articles about Moracin C 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: 30.0%

6-methoxy-2-(3,5-dimethoxy-4-(3-methylbut-2-enyl)phenyl)benzofuran (69120-11-2) → moracin C (69120-06-5) + 2-(3,5-dimethoxy-4-(3-methylbut-2-enyl)phenyl)benzofuran-6-ol + 4'-[3-methyl-2-butenyl]-3'-methoxy-5',6-dihydroxy-2-phenylbenzofuran

Guidance literature:

With 1-methyl-pyrrolidin-2-one; sodium hydroxide; 1-dodecylthiol; at 130 ℃; for 24h; Inert atmosphere;

DOI:10.3390/molecules26051327

Reference yield:

6-hydroxybenzofuran-3-one (6272-26-0) → moracin C (69120-06-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C

2.1: sodium tetrahydroborate / methanol / 4 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: -78 - 20 °C

3.3: 20 °C / pH 5

4.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere

5.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C

6.1: n-butyllithium / hexane; cyclohexane / 0.5 h / Inert atmosphere; Heating

6.2: 2 h / Inert atmosphere; Heating

7.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; palladium diacetate; potassium carbonate; diphenylphosphane; tricyclohexylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; cyclohexane; water;

DOI:10.1016/j.tetlet.2015.05.093

Reference yield:

2-(3,5-dimethoxyphenyl)-6-hydroxybenzofuran (134937-20-5) → moracin C (69120-06-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

3: Ph₂PLi / tetrahydrofuran; hexane / 16 h / Heating

4: Bu₄NF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; lithium diphenylphosphide; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

upstream raw materials:

2,4-diacetoxybenzaldehyde

2-(3,5-dimethoxyphenyl)-6-hydroxybenzofuran

3,5-dimethoxybenzoic acid

5-acetoxy-2-acetoxymethylphenol

Downstream raw materials:

moracin D