(4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Base Information

Chemical Name:(4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde
CAS No.:1383736-56-8
Molecular Formula:C₁₆H₁₆BrNO₂
Molecular Weight:334.213
Hs Code.:

Synonyms:(4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

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Chemical Property of (4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

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Technology Process of (4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

There total 5 articles about (4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde 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:

: 1383736-55-7
(4R,5S)-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

: 1383736-56-8
(4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Guidance literature:: With 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate; In dichloromethane; at 40 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol301461e

Reference yield:

: 1383736-53-5
(4R,5R)-methyl 5-methyl-4-(pent-4-en-1-yl)-2-phenyl-4,5-dihydrooxazole-4-carboxylate

: 1383736-56-8
(4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,O-dimethylhydroxylamine*hydrochloride / tetrahydrofuran / 0.08 h / Inert atmosphere

1.2: -5 - 20 °C / Inert atmosphere

2.1: ozone / ethyl acetate / -78 °C

2.2: 8 h / Inert atmosphere; Reflux

3.1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

4.1: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); bromine; N,O-dimethylhydroxylamine*hydrochloride; silica gel; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 3.1: Aldol condensation;
DOI:10.1021/ol301461e

Reference yield:

: 1383736-52-4
4-((4R,5R)-4-acetyl-5-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)butanal

: 1383736-56-8
(4R,5S)-8-bromo-4,6-dimethyl-2-phenyl-3-oxa-1-azaspiro[4.4]nona-1,6-diene-7-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: silica gel; N-ethyl-N,N-diisopropylamine / toluene / 48 h / 75 °C

2: 2,2'-azobis(isobutyronitrile); bromine; potassium carbonate / dichloromethane / 40 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); bromine; silica gel; potassium carbonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1: Aldol condensation;
DOI:10.1021/ol301461e