(3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

Base Information

Chemical Name:(3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one
CAS No.:1350803-21-2
Molecular Formula:C₁₅H₁₈O₃
Molecular Weight:246.306
Hs Code.:

Synonyms:(3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

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Chemical Property of (3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

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Technology Process of (3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

There total 20 articles about (3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-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: 62.0%

: 1350803-20-1
2-((2R,4S)-6-methoxy-7-methyl-4-vinylchroman-2-yl)propan-2-ol

: 1350803-21-2
(3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

: 1350803-23-4
2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

: 1242430-87-0
2-((3S,5S)-5,6-dihydroxy-6-methylhept-1-en-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

Guidance literature:: With nitric acid; In 1,4-dioxane; water; at 20 ℃; for 0.05h;
DOI:10.1021/jo201971g

Reference yield: 23.0%

: 1350803-20-1
2-((2R,4S)-6-methoxy-7-methyl-4-vinylchroman-2-yl)propan-2-ol

: 1350803-21-2
(3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

: 1350803-22-3
(2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine

: 1350803-23-4
2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

: 1242430-87-0
2-((3S,5S)-5,6-dihydroxy-6-methylhept-1-en-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

Guidance literature:: With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1021/jo201971g

Reference yield:

: 1350803-13-2
1-(2-hydroxy-5-methoxy-4-methylphenyl)prop-2-en-1-one

: 1350803-21-2
(3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one

: 1350803-23-4
2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

: 1242430-87-0
2-((3S,5S)-5,6-dihydroxy-6-methylhept-1-en-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 1 h / 20 °C / Inert atmosphere

2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 °C

4.1: methylmagnesium bromide / diethyl ether / 3 h / -78 - 20 °C / Inert atmosphere

5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / N,N-dimethyl-formamide / 7 h / 20 - 80 °C / Inert atmosphere

7.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C / Inert atmosphere

7.2: 6 h / 150 °C / Inert atmosphere

8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C

With triethylsilane; dmap; sodium tetrahydroborate; ammonium cerium (IV) nitrate; boron trifluoride diethyl etherate; methylmagnesium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo201971g