Bicyclo[5.3.1]undec-8-en-3-one, 4,8,11,11-tetramethyl-2-[[2-(methylamino)phenyl]sulfinyl]-

Base Information

Chemical Name:Bicyclo[5.3.1]undec-8-en-3-one, 4,8,11,11-tetramethyl-2-[[2-(methylamino)phenyl]sulfinyl]-
CAS No.:105631-11-6
Molecular Formula:C₂₂H₃₁NO₂S
Molecular Weight:373.56
Hs Code.:
Mol file:105631-11-6.mol

Synonyms:

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Chemical Property of Bicyclo[5.3.1]undec-8-en-3-one, 4,8,11,11-tetramethyl-2-[[2-(methylamino)phenyl]sulfinyl]-

Chemical Property:

Purity/Quality:

Safty Information:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of Bicyclo[5.3.1]undec-8-en-3-one, 4,8,11,11-tetramethyl-2-[[2-(methylamino)phenyl]sulfinyl]-

There total 18 articles about Bicyclo[5.3.1]undec-8-en-3-one, 4,8,11,11-tetramethyl-2-[[2-(methylamino)phenyl]sulfinyl]- 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:

: 105631-37-6
methyl 3-(3,3-ethylenedioxybutyl)-2,4,4-trimethyl-5-oxo-3-cyclohexenecarboxylate

: 105631-11-6
4,8,11,11-tetramethyl-2-(2-methylamino)phenyllsulfinyl-3-oxobicyclo<5.3.1>undec-8-ene

Guidance literature:: Multi-step reaction with 14 steps

1: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

2: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

3: 84.3 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 15 h / Ambient temperature

4: 1.73 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

5: 1.94 g / pyridine / 1 h / Ambient temperature

6: p-TsOH / acetone / 2.5 h / Ambient temperature

7: 1.) n-butyl lithium; 2.) Ac₂O; 60percent HClO₄ / 1.) hexan, THF, rt., 1 h then 0 deg C, 2 h; 2.) pyridine rt., 2 h; Et₂O, rt., 10 min

8: 70.4 percent / Jones reagent / acetone / 0.5 h / Ambient temperature

9: 1.) NaOH; 2.) Et₃N / 1.) aq. MeOH, 50 deg C, 2 h; 2.) CH₂Cl₂, 0 deg C, 1 h

10: oxalyl chloride / benzene / 1 h / Ambient temperature

11: K₂CO₃ / tetrahydrofuran / 3 h / 0 °C

12: K₂CO₃, NaBH₄ / dimethylformamide / 40 h / 130 - 135 °C

13: 85.9 percent / NaIO₄ / methanol; H₂O / 5 h / Ambient temperature

14: n-butyl lithium/diisopropylamine / hexane; tetrahydrofuran / -65 deg C, 30 min then 0 deg C, 4.5 h

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; jones reagent; oxalyl dichloride; hydrogen; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.36.4722

Reference yield:

: 105631-36-5
2-ethylenedioxy-4-(2,6,6-trimethyl-5-nitromethyl-3-oxo-1-cyclohexen-1-yl)butane

: 105631-11-6
4,8,11,11-tetramethyl-2-(2-methylamino)phenyllsulfinyl-3-oxobicyclo<5.3.1>undec-8-ene

Guidance literature:: Multi-step reaction with 18 steps

1: 88.4 percent / aq. 16percent titanium trichloride, AcONH₄, MeONa / H₂O; methanol / 0.33 h / Ambient temperature

2: 85.5 percent / Jones reagent / acetone / 0.5 h / 5 °C

3: 470 mg / K₂CO₃ / acetone / Heating

4: p-toluenesulfonic acid, Zeolite A-3 / benzene / 1 h / Heating

5: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

6: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

7: 84.3 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 15 h / Ambient temperature

8: 1.73 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

9: 1.94 g / pyridine / 1 h / Ambient temperature

10: p-TsOH / acetone / 2.5 h / Ambient temperature

11: 1.) n-butyl lithium; 2.) Ac₂O; 60percent HClO₄ / 1.) hexan, THF, rt., 1 h then 0 deg C, 2 h; 2.) pyridine rt., 2 h; Et₂O, rt., 10 min

12: 70.4 percent / Jones reagent / acetone / 0.5 h / Ambient temperature

13: 1.) NaOH; 2.) Et₃N / 1.) aq. MeOH, 50 deg C, 2 h; 2.) CH₂Cl₂, 0 deg C, 1 h

14: oxalyl chloride / benzene / 1 h / Ambient temperature

15: K₂CO₃ / tetrahydrofuran / 3 h / 0 °C

16: K₂CO₃, NaBH₄ / dimethylformamide / 40 h / 130 - 135 °C

17: 85.9 percent / NaIO₄ / methanol; H₂O / 5 h / Ambient temperature

18: n-butyl lithium/diisopropylamine / hexane; tetrahydrofuran / -65 deg C, 30 min then 0 deg C, 4.5 h

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; jones reagent; titanium(III) chloride; oxalyl dichloride; Zeolite A-3; ammonium acetate; hydrogen; sodium methylate; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.36.4722

Reference yield:

: 123886-83-9
2,2,4-trimethyl-5-oxo-3-(3-oxobutyl)cyclohexanecarboxylic acid

: 105631-11-6
4,8,11,11-tetramethyl-2-(2-methylamino)phenyllsulfinyl-3-oxobicyclo<5.3.1>undec-8-ene

Guidance literature:: Multi-step reaction with 16 steps

1: 470 mg / K₂CO₃ / acetone / Heating

2: p-toluenesulfonic acid, Zeolite A-3 / benzene / 1 h / Heating

3: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

4: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

5: 84.3 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 15 h / Ambient temperature

6: 1.73 g / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

7: 1.94 g / pyridine / 1 h / Ambient temperature

8: p-TsOH / acetone / 2.5 h / Ambient temperature

9: 1.) n-butyl lithium; 2.) Ac₂O; 60percent HClO₄ / 1.) hexan, THF, rt., 1 h then 0 deg C, 2 h; 2.) pyridine rt., 2 h; Et₂O, rt., 10 min

10: 70.4 percent / Jones reagent / acetone / 0.5 h / Ambient temperature

11: 1.) NaOH; 2.) Et₃N / 1.) aq. MeOH, 50 deg C, 2 h; 2.) CH₂Cl₂, 0 deg C, 1 h

12: oxalyl chloride / benzene / 1 h / Ambient temperature

13: K₂CO₃ / tetrahydrofuran / 3 h / 0 °C

14: K₂CO₃, NaBH₄ / dimethylformamide / 40 h / 130 - 135 °C

15: 85.9 percent / NaIO₄ / methanol; H₂O / 5 h / Ambient temperature

16: n-butyl lithium/diisopropylamine / hexane; tetrahydrofuran / -65 deg C, 30 min then 0 deg C, 4.5 h

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; perchloric acid; jones reagent; oxalyl dichloride; Zeolite A-3; hydrogen; sodium acetate; acetic anhydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.36.4722