(+/-)-2-allyl-2,3-dimethylcyclohexanone

Base Information

• Chemical Name: (+/-)-2-allyl-2,3-dimethylcyclohexanone
• CAS No.: 127717-11-7
• Molecular Formula: C₁₁H₁₈O
• Molecular Weight: 166.263
• Mol file: 127717-11-7.mol

Synonyms:

Chemical Property of (+/-)-2-allyl-2,3-dimethylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-2-allyl-2,3-dimethylcyclohexanone

There total 1 articles about (+/-)-2-allyl-2,3-dimethylcyclohexanone 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: 72.0%

2-methyl-2-cyclohexen-1-one (1121-18-2) + allyl bromide (106-95-6) → (+/-)-2-allyl-2,3-dimethylcyclohexanone (100779-93-9,100779-94-0,127717-11-7,129523-91-7)

Guidance literature:

2-methyl-2-cyclohexen-1-one; Me₂CuLi; In diethyl ether; at 0 ℃;

allyl bromide; In 1,2-dimethoxyethane; at 0 ℃;

DOI:10.1021/ol030115i

Reference yield: 70.0%

(+/-)-2-allyl-2,3-dimethylcyclohexanone (100779-93-9,100779-94-0,127717-11-7,129523-91-7) → (+/-)-2α-allyl-2,3β-dimethylcyclohexan-1-β-ol

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -78 ℃; for 1h;

DOI:10.1021/ol030115i

Reference yield:

(+/-)-2-allyl-2,3-dimethylcyclohexanone (100779-93-9,100779-94-0,127717-11-7,129523-91-7) → (+/-)-6α-[(3E,7E)-9-(tert-butyldiphenylsilyloxy)-3,7-dimethylnona-3,7-dienyl]-3-methoxy-5β,6-dimethylcyclohex-2-en-1-one

Guidance literature:

Multi-step reaction with 15 steps

1.1: 70 percent / lithium aluminium hydride / diethyl ether / 1 h / -78 °C

2.1: 88 percent / sodium hydride / dimethylformamide / 1.5 h

3.1: borane-dimethyl sulfide complex / tetrahydrofuran / 2 h / 0 - 20 °C

3.2: sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 2 h / Heating

4.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

5.1: triphenylphosphine / CH₂Cl₂ / 0.25 h / 0 - 20 °C

6.1: 81 percent / n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C

7.1: Cp₂ZrCl₂ / CH₂Cl₂; hexane / 20 °C

7.2: 68 percent / iodine / CH₂Cl₂; hexane; tetrahydrofuran / -45 - 20 °C

8.1: cyclohexene; borane-dimethyl sulfide complex / tetrahydrofuran / 2.08 h / 0 - 20 °C

8.2: 94 percent / aqueous K₃PO₄ / PdCl₂(PPh₃)2 / dimethylformamide; tetrahydrofuran; ethanol / 12 h

9.1: 87 percent / DDQ; water / CH₂Cl₂ / 0.33 h / 0 °C

10.1: 91 percent / NMO; 4 Angstroem molecular sieves; TPAP / CH₂Cl₂ / 3 h / 20 °C

11.1: diisopropylamine; n-butyllithium; HMPA / tetrahydrofuran; hexane / 0.75 h / -78 °C

11.2: PhSeBr / tetrahydrofuran; hexane / -78 - 20 °C

11.3: 34 percent / hydrogen peroxide / tetrahydrofuran / 3 h / 0 - 20 °C

12.1: 94 percent / H₂O₂; K₂CO₃ / tetrahydrofuran; methanol; H₂O / 0 - 20 °C

13.1: 79 percent / 1,2-diiodoethane; Sm; methanol / tetrahydrofuran / 0.08 h / -90 °C

14.1: 81 percent / PCC / CH₂Cl₂

15.1: 49 percent / K₂CO₃ / acetone / 1 h / 20 °C

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; samarium; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; oxalyl dichloride; 1,2-Diiodoethane; dimethylsulfide borane complex; 4 A molecular sieve; water; dihydrogen peroxide; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; cyclohexene; zirconocene dichloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 4.1: Swern oxidation / 5.1: Corey-Fuchs homologation / 7.1: Negishi carboalumination / 8.2: Suzuki coupling;

DOI:10.1021/ol030115i

upstream raw materials:

2-methyl-2-cyclohexen-1-one

allyl bromide