(+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone

Base Information

• Chemical Name: (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone
• CAS No.: 130583-84-5
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 130583-84-5.mol

Synonyms:

Chemical Property of (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone

There total 13 articles about (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone 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:

(+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(5-hydroxy-3-methyl-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone (130583-83-4) → (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone (130583-84-5)

Guidance literature:

With manganese(IV) oxide; In acetone; Ambient temperature;

Reference yield:

(Z)-3-methylpent-2-en-4-ynol (6153-05-5,105-29-3) → (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone (130583-84-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 64 percent / n-butyl-Li / hexane; tetrahydrofuran / 1) -5 deg C 2) -60 deg C to r.t.

2: pyridine, 4-dimethylaminopyridine / 1 h / Ambient temperature

3: glacical acetic acid, H₂O / 80 °C

4: 70 percent / pyridinium dichromate / CH₂Cl₂ / Ambient temperature

5: 100 percent / 5M NaOH / methanol / 1 h / Ambient temperature

6: pyridinium p-tosylate / benzene / Heating

7: Na-bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran / 1) 0 deg C, 1,5 h 2) r.t., 1 h

8: 1M HCl / acetone / Ambient temperature

9: MnO₂ / acetone / Ambient temperature

With pyridine; hydrogenchloride; dmap; manganese(IV) oxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; water; pyridinium p-toluenesulfonate; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; benzene;

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → (+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(3-methyl-5-oxo-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone (130583-84-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 73 percent Turnov_. / 5M NaOH / ethanol / 24 h / 85 °C

2: 99 percent / imidazole / dimethylformamide / Ambient temperature

3: 64 percent / n-butyl-Li / hexane; tetrahydrofuran / 1) -5 deg C 2) -60 deg C to r.t.

4: pyridine, 4-dimethylaminopyridine / 1 h / Ambient temperature

5: glacical acetic acid, H₂O / 80 °C

6: 70 percent / pyridinium dichromate / CH₂Cl₂ / Ambient temperature

7: 100 percent / 5M NaOH / methanol / 1 h / Ambient temperature

8: pyridinium p-tosylate / benzene / Heating

9: Na-bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran / 1) 0 deg C, 1,5 h 2) r.t., 1 h

10: 1M HCl / acetone / Ambient temperature

11: MnO₂ / acetone / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; manganese(IV) oxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; water; pyridinium p-toluenesulfonate; acetic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

upstream raw materials:

(+)-4(1E,3Z)-(4S,5S)-4-hydroxy-4-(5-hydroxy-3-methyl-1,3-pentadienyl)-3,3,5-trimethylcyclohexanone

(Z)-3-methylpent-2-en-4-ynol

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(+)-(4R,6S)-4-hydroxy-2,2,6-trimethylcyclohexanone

Downstream raw materials:

(+)-(4S,5S)-dihydroabscisic acid

(+)-(4S,5S)-methyl dihydroabscisate