6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine

Base Information

• Chemical Name: 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine
• CAS No.: 638133-16-1
• Molecular Formula: C₁₆H₂₅NO₂Si
• Molecular Weight: 291.466

Synonyms:6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine

Chemical Property of 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine

Chemical Property:

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Technology Process of 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine

There total 5 articles about 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]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%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide (638133-04-7) → 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine (638133-16-1)

Guidance literature:

6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide; With triethylamine; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 3.08333h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.12.066

Reference yield: 95.0%

trimethylsilyl bromide (2857-97-8) + 6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide (638133-04-7) → 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine (638133-16-1)

Guidance literature:

With triethylamine; In dichloromethane; at -78 ℃; for 24h;

DOI:10.1021/jo034669a

Reference yield:

1-phenyl-2-nitroprop-1-ene (705-60-2,18315-84-9,58321-79-2) → 6,6-dimethyl-3-methylene-4-phenyl-2-(trimethylsilyloxy)-2,3,5,6-tetrahydro-4H-[1,2]oxazine (638133-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SnCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

1.2: 60 percent / CH₂Cl₂ / 0.08 h / -94 °C

2.1: 95 percent / Et₃N / CH₂Cl₂ / 24 h / -78 °C

With tin(IV) chloride; triethylamine; In dichloromethane;

DOI:10.1021/jo034669a

upstream raw materials:

trimethylsilyl bromide

6,6-dimethyl-5,6-dihydro-3-methyl-4-phenyl-1,2-oxazine N-oxide

1-phenyl-2-nitroprop-1-ene

trimethylsilyl trifluoromethanesulfonate

Downstream raw materials:

3-(bromomethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine

(6,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazin-3-yl)methyl 2,2,2-trifluoroacetate

3-(bromomethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-[1,2]oxazine 2-oxide

3-(iodomethyl)-6,6-dimethyl-4-phenyl-5,6-dihydro-4H-[1,2]oxazine 2-oxide

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