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

Base Information

• Chemical Name: (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine
• CAS No.: 1350803-22-3
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333

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

Chemical Property of (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine

Chemical Property:

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Technology Process of (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine

There total 10 articles about (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine 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: 23.0%

2-((2R,4S)-6-methoxy-7-methyl-4-vinylchroman-2-yl)propan-2-ol (1350803-20-1) → (3R,5S,9aR)-2,2,8-trimethyl-5-vinyl-4,5-dihydro-2H-3,9a-epoxybenzo[b]oxepin-7(3H)-one (1350803-21-2) + (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine (1350803-22-3) + 2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione (1350803-23-4) + 2-((3S,5S)-5,6-dihydroxy-6-methylhept-1-en-3-yl)-5-methylcyclohexa-2,5-diene-1,4-dione (1242430-87-0)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/jo201971g

Reference yield:

1-(2-hydroxy-5-methoxy-4-methylphenyl)prop-2-en-1-one (1350803-13-2) → (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine (1350803-22-3) + 2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione (1350803-23-4)

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

Reference yield:

1-(2-Hydroxy-5-methoxy-4-methylphenyl)-3-(phenylthio)propan-1-one (1350803-14-3) → (2R,5S)-7-methoxy-3,3,8-trimethyl-5-vinyl-3,5-dihydro-2H-2,5-methanobenzo[e][1,4]dioxepine (1350803-22-3) + 2-((2S,4R)-4-hydroxy-5,5-dimethyl-2-vinyltetrahydrofuran-2-yl)-5-methylcyclohexa-2,5-diene-1,4-dione (1350803-23-4)

Guidance literature:

Multi-step reaction with 7 steps

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

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

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

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

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / N,N-dimethyl-formamide / 7 h / 20 - 80 °C / Inert atmosphere

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

6.2: 6 h / 150 °C / Inert atmosphere

7.1: 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; 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;

DOI:10.1021/jo201971g

upstream raw materials:

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

1-(2-Hydroxy-5-methoxy-4-methylphenyl)-3-(phenylthio)propan-1-one

C₂₂H₂₆O₅S

tert-butyl (2-(1-hydroxy-3-(phenylthio)propyl)-4-methoxy-5-methylphenyl) carbonate

Downstream raw materials:

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

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