(+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE

Base Information

• Chemical Name: (+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE
• CAS No.: 153153-60-7
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.28
• Mol file: 153153-60-7.mol

Synonyms:(-)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE;(+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE;(4aR-trans)-4a,5,6,10b-Tetrahydro-9-Methoxy-2H-naphth[1,2-b]-1,4-oxazin-3(4H)-one

Chemical Property of (+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE

Chemical Property:

• Melting Point: 216-218°C
• Boiling Point: 468.7±45.0 °C(Predicted)
• PKA: 13.95±0.20(Predicted)
• Density: 1.191±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

(+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO(1,2-B)(1,4)OXAZIN-3-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A dopamine antagonist. A dopaminergic ligand

Technology Process of (+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE

There total 8 articles about (+)-3,4,4A,5,6,10B-HEXAHYDRO-9-METHOXY-2H-NAPHTHO[1,2-B][1,4]OXAZIN-3-ONE 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: 78.5%

trans-2-(chloroacetylamino)-7-methoxy-1-tetralol (92421-91-5,153153-59-4,99833-89-3) → trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazin-3-one (92422-00-9,153153-60-7)

Guidance literature:

With sodium hydroxide; In water; isopropyl alcohol; for 2h; Ambient temperature;

Reference yield:

7-Methoxy-1-tetralone (6836-19-7) → trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazin-3-one (92422-00-9,153153-60-7)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium tert-butoxide, isoamyl nitrite / diethyl ether; butan-1-ol / 4 h / Ambient temperature

2: H₂ / 10percent Pd/C / tetrahydrofuran

3: 60 percent / sodium borohydride / ethanol

4: LiAlH₄ / tetrahydrofuran; ethane-1,2-diol; dimethyl ether / 1 h / Heating

5: 1.) Na₂CO₃, 2.) NaH / 1.) ethyl acetate, 1 h, 2.) CH₃CN, THF, 1 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; potassium tert-butylate; hydrogen; sodium hydride; sodium carbonate; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; Dimethyl ether; ethylene glycol; butan-1-ol;

DOI:10.1021/jm00378a014

Reference yield:

2-hydroximino-7-methoxy-1-tetralone (2471-80-9) → trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazin-3-one (92422-00-9,153153-60-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran

2: 60 percent / sodium borohydride / ethanol

3: LiAlH₄ / tetrahydrofuran; ethane-1,2-diol; dimethyl ether / 1 h / Heating

4: 1.) Na₂CO₃, 2.) NaH / 1.) ethyl acetate, 1 h, 2.) CH₃CN, THF, 1 h

With sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium hydride; sodium carbonate; palladium on activated charcoal; In tetrahydrofuran; ethanol; Dimethyl ether; ethylene glycol;

DOI:10.1021/jm00378a014

upstream raw materials:

trans-2-(chloroacetylamino)-7-methoxy-1-tetralol

chloroacetyl chloride

(1RS,2RS)-2-amino-1,2,3,4-tetrahydro-7-methoxy-1-naphthol

2-amino-7-methoxy-1-tetralone hydrochloride

Refernces

• 1、 Perrone,Berardi,Bettoni,Tortorella. "Synthesis of rigid dopamine congeners: Naphtho[1,4]oxazine derivatives". . p. 422 - 428. Retrieved 2007/10/02.