(1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one

Base Information

Chemical Name:(1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one
CAS No.:123887-55-8
Molecular Formula:C₂₂H₃₃NO₂S
Molecular Weight:375.576
Hs Code.:

Synonyms:

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Chemical Property of (1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one

Chemical Property:

Purity/Quality:

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Technology Process of (1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one

There total 23 articles about (1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one 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:

: 123887-54-7,124093-60-3
3,5ξ,10α-trimethyl-7β,11β-dimethylmethano-14-thia-3-aza-1,2-benzocyclotetradecen-4-one 14-oxide

: 123887-55-8
(1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1248/cpb.36.4711

Reference yield:

: 123887-37-6,123906-77-4
bicyclic hemiacetal of 4α-formyl-6α-hydroxymethyl-1,5,5-trimethylcyclohexene

: 123887-55-8
(1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one

Guidance literature:: Multi-step reaction with 19 steps

1: 70.5 percent / toluene / 24 h / 100 °C

2: 97.3 percent / PtO₂, hydrogen / ethyl acetate / 2 h / Ambient temperature

3: 100 percent / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

4: dimethylsulfoxide / 7 h / 100 - 105 °C

5: 240 mg / LiBH₄ / diethyl ether / 3 h / Heating

6: pyridinium p-toluenesulfonate / CH₂Cl₂ / 13 h / Ambient temperature

7: 185 mg / diisobutylaluminum hydride / hexane; toluene / 1 h / Ambient temperature

8: 176 mg / 1.) LiAlH₄; 2.) NaOH, water / diethyl ether / 0.5 h / -15 °C

9: 179 mg / pyridine / 1 h / Ambient temperature

10: p-TsOH / ethanol / 3 h / Ambient temperature

11: Jones reagent / acetone / 0.5 h / Ambient temperature

12: oxalyl chloride / benzene / 1 h / 60 °C

13: K₂CO₃ / tetrahydrofuran / 0.17 h / 0 °C

14: 99 mg / K₂CO₃ / methanol / 1.5 h / 0 °C

15: pyridine / 12 h

16: 26 percent / tert-BuOK / dioxane; dimethylformamide / 7 h / 65 - 70 °C

17: 87.8 percent / butyl lithium, diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

18: 90.9 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.17 h / 0 °C

19: 15 mg / hexamethylphosphoramide, lithium diisopropylamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; platinum(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; jones reagent; oxalyl dichloride; potassium tert-butylate; water; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1248/cpb.36.4711

Reference yield:

: 123887-47-8
3-(3α-cyanomethyl-2,2,4α-trimethylcyclohexan-1α-yl)propan-1-ol

: 123887-55-8
(1S,7S,8S)-3,8,11,11-Tetramethyl-5-(2-methylamino-benzenesulfinyl)-bicyclo[5.3.1]undecan-4-one

Guidance literature:: Multi-step reaction with 14 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 13 h / Ambient temperature

2: 185 mg / diisobutylaluminum hydride / hexane; toluene / 1 h / Ambient temperature

3: 176 mg / 1.) LiAlH₄; 2.) NaOH, water / diethyl ether / 0.5 h / -15 °C

4: 179 mg / pyridine / 1 h / Ambient temperature

5: p-TsOH / ethanol / 3 h / Ambient temperature

6: Jones reagent / acetone / 0.5 h / Ambient temperature

7: oxalyl chloride / benzene / 1 h / 60 °C

8: K₂CO₃ / tetrahydrofuran / 0.17 h / 0 °C

9: 99 mg / K₂CO₃ / methanol / 1.5 h / 0 °C

10: pyridine / 12 h

11: 26 percent / tert-BuOK / dioxane; dimethylformamide / 7 h / 65 - 70 °C

12: 87.8 percent / butyl lithium, diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

13: 90.9 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.17 h / 0 °C

14: 15 mg / hexamethylphosphoramide, lithium diisopropylamide / hexane; tetrahydrofuran / 0.5 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; jones reagent; oxalyl dichloride; potassium tert-butylate; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1248/cpb.36.4711