1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Base Information

• Chemical Name: 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene
• CAS No.: 216978-12-0
• Molecular Formula: C₁₈H₂₇BrO₂
• Molecular Weight: 355.315
• Mol file: 216978-12-0.mol

Synonyms:1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Chemical Property of 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

There total 14 articles about 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-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: 90.0%

(E)-6-Bromo-1-[5-(1-methoxymethoxy-allyl)-2,6,6-trimethyl-cyclohex-1-enyl]-hex-2-en-1-one (216978-11-9) → 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene (216978-12-0)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 50 - 60 ℃; for 2h;

DOI:10.1039/a805268i

Reference yield:

ethyl 2-acetyl-3-methylbut-2-enoate (35044-52-1) → 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene (216978-12-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / tetrahydrofuran / Ambient temperature

2: 92 percent / DIBAL-H / toluene / -60 °C

3: 93 percent / PTSA / benzene / 65 °C

4: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

5: 79 percent / BF₃*OEt₂ / toluene / 1.) -78 deg C, 5 min, 2.) -78 deg C, 10 h

6: 72 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) r.t., 1 h

7: 91 percent / Hunig's base / CH₂Cl₂ / 14 h / Ambient temperature

8: 98 percent / K₂CO₃ / methanol / 14 h / Ambient temperature

9: 99 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

11: 84 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

12: 90 percent / HCl, H₂O / tetrahydrofuran / 2 h / 50 - 60 °C

With hydrogenchloride; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1039/a805268i

Reference yield:

2-isopropenyl-3-methyl-crotonic acid (4412-05-9) → 1-((E)-6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene (216978-12-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 73 percent / K₂CO₃ / acetone / 24 h / Ambient temperature

2: 92 percent / DIBAL-H / toluene / 2 h / -60 °C

3: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

4: 79 percent / BF₃*OEt₂ / toluene / 1.) -78 deg C, 5 min, 2.) -78 deg C, 10 h

5: 72 percent / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) r.t., 1 h

6: 91 percent / Hunig's base / CH₂Cl₂ / 14 h / Ambient temperature

7: 98 percent / K₂CO₃ / methanol / 14 h / Ambient temperature

8: 99 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

10: 84 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

11: 90 percent / HCl, H₂O / tetrahydrofuran / 2 h / 50 - 60 °C

With hydrogenchloride; dmap; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1039/a805268i

upstream raw materials:

(E)-6-Bromo-1-[5-(1-methoxymethoxy-allyl)-2,6,6-trimethyl-cyclohex-1-enyl]-hex-2-en-1-one

ethyl 2-acetyl-3-methylbut-2-enoate

2-isopropenyl-3-methyl-crotonic acid

2-isopropenyl-3-methyl-crotonic acid methyl ester

Downstream raw materials:

1-((E)-6-Bromo-1-oxohex-2-enyl)-2,6,6-trimethyl-5-(1-oxoprop-2-enyl)cyclohex-1-ene

1-((E)-6-Iodo-1-oxohex-2-enyl)-2,6,6-trimethyl-5-(1-oxoprop-2-enyl)cyclohex-1-ene