1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

Base Information

Chemical Name:1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene
CAS No.:216978-57-3
Molecular Formula:C₂₀H₂₉BrO₃
Molecular Weight:397.352
Hs Code.:

Synonyms:1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

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Chemical Property of 1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

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Technology Process of 1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

There total 13 articles about 1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene 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: 81.0%

: 217076-35-2
1-(2-Hydroxybut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

: 216978-57-3
1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1039/a805268i

Reference yield:

: 3-(2-Hydroxy-but-3-enyl)-2,2,4-trimethyl-cyclohex-3-enecarbaldehyde

: 216978-57-3
1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

Guidance literature:: Multi-step reaction with 8 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.33 h / -20 °C

2: 64 percent / chromous chloride / tetrahydrofuran / 3 h / Ambient temperature

3: 2.) chromous chloride, NiCl₂ / 1.) toluene, reflux, 2 h, 2.) DMSO, THF, r.t., 20 h

4: 92 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / 0 °C

5: 85 percent / DDQ, H₂O / CH₂Cl₂ / 3 h / Ambient temperature

6: 96 percent / CBr₄, PPh₃ / CH₂Cl₂ / 3 h / 0 °C

7: 79 percent / HF / acetonitrile / 6 h / Ambient temperature

8: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

With 2,6-dimethylpyridine; chromium dichloride; dmap; carbon tetrabromide; hydrogen fluoride; water; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1039/a805268i

Reference yield:

: 216978-72-2
1-(2-Hydroxyethyl)-2,6,6-trimethyl-5-(1,3-dioxolan-2-yl)cyclohex-1-ene

: 216978-57-3
1-(2-Oxobut-3-enyl)-2,6,6-trimethyl-5-((E)-3-acetoxy-5-bromopent-1-enyl)cyclohex-1-ene

Guidance literature:: Multi-step reaction with 11 steps

1: 94 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

2: 74 percent / CeCl₃ / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1 h; -78 deg C to r.t., 2 h

3: CSA, H₂O / tetrahydrofuran / 3 h / 60 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.33 h / -20 °C

5: 64 percent / chromous chloride / tetrahydrofuran / 3 h / Ambient temperature

6: 2.) chromous chloride, NiCl₂ / 1.) toluene, reflux, 2 h, 2.) DMSO, THF, r.t., 20 h

7: 92 percent / DMAP, Et₃N / CH₂Cl₂ / 2 h / 0 °C

8: 85 percent / DDQ, H₂O / CH₂Cl₂ / 3 h / Ambient temperature

9: 96 percent / CBr₄, PPh₃ / CH₂Cl₂ / 3 h / 0 °C

10: 79 percent / HF / acetonitrile / 6 h / Ambient temperature

11: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

With 2,6-dimethylpyridine; chromium dichloride; dmap; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; carbon tetrabromide; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; water; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1039/a805268i