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

Base Information

• Chemical Name: 1-(6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene
• CAS No.: 216978-16-4
• Molecular Formula: C₁₈H₂₅BrO₂
• Molecular Weight: 353.299
• Mol file: 216978-16-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about 1-(6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-ynyl)-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: 81.0%

1-(6-Bromo-1-oxohex-2-enyl)-5-formyl-2,6,6-trimethylcyclohex-1-ene (189444-04-0) + acetylenemagnesium bromide (4301-14-8) → 1-(6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene (216978-16-4)

Guidance literature:

In tetrahydrofuran; Ambient temperature;

Reference yield:

1-Formyl-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene (189443-99-0) → 1-(6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene (216978-16-4)

Guidance literature:

Multi-step reaction with 4 steps

2: 81 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

3: 89 percent / CSA, H₂O / tetrahydrofuran / 14 h / Heating

4: 81 percent / tetrahydrofuran / 12 h / -78 - 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; water; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a805268i

Reference yield:

5-(1,3-Dioxolan-2-yl)-1-(6-bromo-1-hydroxyhex-2-enyl)-2,6,6-trimethylcyclohex-1-ene (216978-14-2) → 1-(6-Bromo-1-oxohex-2-enyl)-5-(1-hydroxyprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene (216978-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

2: 89 percent / CSA, H₂O / tetrahydrofuran / 14 h / Heating

3: 81 percent / tetrahydrofuran / 12 h / -78 - 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; water; In tetrahydrofuran; dichloromethane;

DOI:10.1039/a805268i

upstream raw materials:

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

acetylenemagnesium bromide

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

2-isopropenyl-3-methyl-crotonic acid

Downstream raw materials:

5-(1-Oxoprop-2-ynyl)-1-(6-iodo-1-oxohex-2-enyl)-2,6,6-trimethylcyclohex-1-ene

1-(6-Bromo-1-oxohex-2-enyl)-5-(1-oxoprop-2-ynyl)-2,6,6-trimethylcyclohex-1-ene