(S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Base Information

• Chemical Name: (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine
• CAS No.: 1360820-29-6
• Molecular Formula: C₁₄H₁₁Cl₂NO
• Molecular Weight: 280.153
• Mol file: 1360820-29-6.mol

Synonyms:(S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Chemical Property of (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine

There total 3 articles about (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine 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: 97.0%

3-(3,4-dichlorophenyl)-2H-benzo[b][1,4]oxazine (1354648-91-1) → (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1360820-29-6)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(-)-SEGphos; hydrogen; iodine; In benzene; at 20 ℃; for 15h; under 20686.5 Torr; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Autoclave;

DOI:10.1002/adsc.201100568

Reference yield:

3-(3,4-dichlorophenyl)-2H-benzo[b][1,4]oxazine (1354648-91-1) → (R)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1354648-89-7) + (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1360820-29-6)

Guidance literature:

With phenanthridine; diiodo(p-cymene)ruthenium(II) dimer; (S)-(-)-3,3’-bisphenyl-1,1’-bi-2-naphthyl phosphoric acid; hydrogen; In dichloromethane; at 20 ℃; for 32h; under 2585.81 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ja211684v

Reference yield:

2-bromo-1-(3,4-dichlorophenyl)ethanone (2632-10-2) + 2-amino-phenol (95-55-6) → (S)-3-(3,4-dichlorophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1360820-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / dichloromethane; water / 20 °C / Inert atmosphere

2: bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(-)-SEGphos; hydrogen; iodine / benzene / 15 h / 20 °C / 20686.5 Torr / Inert atmosphere; Autoclave

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (S)-(-)-SEGphos; hydrogen; iodine; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In dichloromethane; water; benzene;

DOI:10.1002/adsc.201100568

upstream raw materials:

3-(3,4-dichlorophenyl)-2H-benzo[b][1,4]oxazine

2-bromo-1-(3,4-dichlorophenyl)ethanone

2-amino-phenol