Phenoxan

Base Information

• Chemical Name: Phenoxan
• CAS No.: 134332-63-1
• Molecular Formula: C23H25 N O4
• Molecular Weight: 379.456
• NSC Number: 650914
• Nikkaji Number: J493.022C
• Wikidata: Q75069456
• Metabolomics Workbench ID: 116225
• ChEMBL ID: CHEMBL2004336
• Mol file: 134332-63-1.mol

Synonyms:5-ethyl-2-methoxy-3-methyl-6-(2-((E)-3-methyl-4-phenyl-but-3-enyl)oxazol-4-yl)pyran-4-one;phenoxan

Chemical Property of Phenoxan

Chemical Property:

• Vapor Pressure: 1.65E-13mmHg at 25°C
• Boiling Point: 581.4°Cat760mmHg
• Flash Point: 305.4°C
• PSA: 65.47000
• Density: 1.17g/cm³
• LogP: 5.21030
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 379.17835828
• Heavy Atom Count: 28
• Complexity: 670

Purity/Quality:

PHENOXAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1=C(OC(=C(C1=O)C)OC)C2=COC(=N2)CCC(=CC3=CC=CC=C3)C
• Isomeric SMILES: CCC1=C(OC(=C(C1=O)C)OC)C2=COC(=N2)CC/C(=C/C3=CC=CC=C3)/C

Technology Process of Phenoxan

There total 23 articles about Phenoxan 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: 75.0%

3-Ethyl-6-methoxy-5-methyl-2-[2-((E)-3-methyl-4-phenyl-but-3-enyl)-4,5-dihydro-oxazol-4-yl]-pyran-4-one (177366-41-5) → Phenoxan (134332-63-1)

Guidance literature:

With manganese(IV) oxide; In chloroform; for 6h; Heating;

DOI:10.1016/0040-4039(96)00483-2

Reference yield:

2-acetylpropanoic acid ethyl ester (609-14-3) → Phenoxan (134332-63-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 72 percent / NaH, n-BuLi / tetrahydrofuran / 1 h / 0 °C

2: 1.) NaH, LDA; 2.) DBU / 1.) THF, -78 deg C, 1 h; 2.) benzene, 60 deg C, 3 h

3: 61 percent / CH₂Cl₂ / 4 h / Ambient temperature

4: H₂ / Pd/C / methanol / 3 h / 50 °C

5: pyridine; CH₂Cl₂ / 2 h / Ambient temperature

6: K₂CO₃ / methanol / 0.5 h / Ambient temperature

7: OsO₄, NMO / acetonitrile; H₂O / 12 h / Ambient temperature

8: 84 percent / imidazole / dimethylformamide / 4 h / 0 °C

9: 95 percent / pyridine / 1 h / 0 °C

10: 93 percent / NaN₃ / dimethylformamide / 4 h / Ambient temperature

11: H₂ / Pd-C / methanol

12: 93 percent / DCC, HOBt, Et₃N / tetrahydrofuran / 5 h / Ambient temperature

13: 88 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

14: 77 percent / MsCl, Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

15: 75 percent / MnO₂ / CHCl₃ / 6 h / Heating

With 1H-imidazole; manganese(IV) oxide; osmium(VIII) oxide; n-butyllithium; sodium azide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; benzotriazol-1-ol; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00483-2

Reference yield:

2-methyl-3-oxohexanoic acid ethyl ester (29304-40-3) → Phenoxan (134332-63-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) NaH, LDA; 2.) DBU / 1.) THF, -78 deg C, 1 h; 2.) benzene, 60 deg C, 3 h

2: 61 percent / CH₂Cl₂ / 4 h / Ambient temperature

3: H₂ / Pd/C / methanol / 3 h / 50 °C

4: pyridine; CH₂Cl₂ / 2 h / Ambient temperature

5: K₂CO₃ / methanol / 0.5 h / Ambient temperature

6: OsO₄, NMO / acetonitrile; H₂O / 12 h / Ambient temperature

7: 84 percent / imidazole / dimethylformamide / 4 h / 0 °C

8: 95 percent / pyridine / 1 h / 0 °C

9: 93 percent / NaN₃ / dimethylformamide / 4 h / Ambient temperature

10: H₂ / Pd-C / methanol

11: 93 percent / DCC, HOBt, Et₃N / tetrahydrofuran / 5 h / Ambient temperature

12: 88 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

13: 77 percent / MsCl, Et₃N / CH₂Cl₂ / 16 h / Ambient temperature

14: 75 percent / MnO₂ / CHCl₃ / 6 h / Heating

With 1H-imidazole; manganese(IV) oxide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; benzotriazol-1-ol; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(96)00483-2

upstream raw materials:

3-Ethyl-6-methoxy-5-methyl-2-[2-((E)-3-methyl-4-phenyl-but-3-enyl)-4,5-dihydro-oxazol-4-yl]-pyran-4-one

(E)-1-(3-bromo-2-methylprop-1-en-1-yl)benzene

4-hydroxymethyl-2-methyloxazole

2-((E)-3-Methyl-4-phenyl-but-3-enyl)-oxazole-4-carbaldehyde

Refernces

• 1、 Garey, Donna,Ramirez, Mai-Ly,Gonzales, Sam,Wertsching, Alan,Tith, Sovouthy,Keefe, Katie,Pena, Michael R.. "An approach to substituted 4-hydroxypyran-2-ones: The total synthesis of phenoxan". . p. 4853 - 4856. Retrieved 2007/10/03.