1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

Base Information

Chemical Name:1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione
CAS No.:141665-60-3
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

Synonyms:1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

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Chemical Property of 1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

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Technology Process of 1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

There total 10 articles about 1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione 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: 73.3%

: 141665-59-0
1-<5,5-(ethylenedioxy)-2,6,6-trimethyl-1-cyclohexenyl>-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

: 141665-60-3
1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 60 ℃; for 21h;
DOI:10.1021/jo00040a064

Reference yield:

: 114198-58-2
3,3-(ethylenedioxy)-2,2,6-trimethyl-1-cyclohexanone

: 141665-60-3
1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, 2 h, 0 deg C, 2.) 0 deg C

2: 91.4 percent / LiCl / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 24 h / Heating

3: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 6 N NaOH, 30 percent H₂O₂ / 1.) THF, reflux, 1.5 h, 2.) + ethanol, reflux, 1 h

4: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) NEt₃ / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) -> room temperature

5: 89 percent / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 30 min

6: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) NEt₃ / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) -> room temperature

7: 1.) potassium bis(trimethylsilyl)amide, 2.) N-(phenylsulfonyl)phenyloxaziridine / 1.) THF, -78 deg C, 15 min, 2.) 30 min, -78 deg C

8: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) NEt₃ / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) -> room temperature

9: 2.) 0.1 N HCl / 1.) deuterated benzene, 80 deg C, 3 h, 2.) THF, room temperature, 30 min

10: 73.3 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 21 h / 60 °C

With hydrogenchloride; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water;
DOI:10.1021/jo00040a064

Reference yield:

: 141665-41-0
5,5-(ethylenedioxy)-2,6,6-trimethyl-1-cyclohexenyl trifluoromethanesulfonate

: 141665-60-3
1-(5-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2-(1-methyl-4-oxo-2-cyclohexenyl)-1,2-ethandione

Guidance literature:: Multi-step reaction with 9 steps

1: 91.4 percent / LiCl / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 24 h / Heating

2: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 6 N NaOH, 30 percent H₂O₂ / 1.) THF, reflux, 1.5 h, 2.) + ethanol, reflux, 1 h

3: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) NEt₃ / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) -> room temperature

4: 89 percent / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 30 min

5: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) NEt₃ / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) -> room temperature

6: 1.) potassium bis(trimethylsilyl)amide, 2.) N-(phenylsulfonyl)phenyloxaziridine / 1.) THF, -78 deg C, 15 min, 2.) 30 min, -78 deg C

7: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) NEt₃ / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) -> room temperature

8: 2.) 0.1 N HCl / 1.) deuterated benzene, 80 deg C, 3 h, 2.) THF, room temperature, 30 min

9: 73.3 percent / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 21 h / 60 °C

With hydrogenchloride; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water;
DOI:10.1021/jo00040a064