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CAS No.: | 121629-14-9 |
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Name: | Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester |
Article Data: | 3 |
Molecular Structure: | |
Formula: | C8H12 F2 O2 |
Molecular Weight: | 178.179 |
Synonyms: | Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester |
Density: | 1.13g/cm3 |
Boiling Point: | 181.8oC at 760 mmHg |
Flash Point: | 62.4oC |
PSA: | 26.30000 |
LogP: | 1.98490 |
4,4-difluorocyclohexanecarboxylic acid
methanol
methyl 4,4-difluorocyclohexane-1-carboxylate
Conditions | Yield |
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With sulfuric acid at 0 - 70℃; for 16h; | 90.82% |
sulfuric acid for 16h; Reflux; |
methyl 4,4-difluorocyclohexane-1-carboxylate
dimethyl methane phosphonate
dimethyl [2-(4,4-difluorocyclohexyl)-2-oxoethyl]phosphonate
Conditions | Yield |
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Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: methyl 4,4-difluorocyclohexane-1-carboxylate In tetrahydrofuran at -78 - 0℃; for 1.5h; Inert atmosphere; | 82% |
methyl 4,4-difluorocyclohexane-1-carboxylate
(4,4-difluorocyclohexyl)methanol
Conditions | Yield |
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With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere; | 81% |
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With potassium hydroxide In tetrahydrofuran; diethyl ether; water at 0℃; for 1h; Inert atmosphere; | 81% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Inert atmosphere; | 77% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; | 71.55% |
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; ethanol at 0 - 20℃; |
chloro-trimethyl-silane
methyl 4,4-difluorocyclohexane-1-carboxylate
Conditions | Yield |
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Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h; | 72% |
methyl 4,4-difluorocyclohexane-1-carboxylate
methyl iodide
methyl 4,4-difluoro-1-methylcyclohexanecarboxylate
Conditions | Yield |
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Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 2h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; |
methyl 4,4-difluorocyclohexane-1-carboxylate
(2S,3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-methylphenyl)6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere View Scheme |
methyl 4,4-difluorocyclohexane-1-carboxylate
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
Conditions | Yield |
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Multi-step reaction with 7 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere 7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme |
methyl 4,4-difluorocyclohexane-1-carboxylate
(2S,3R4R5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere 5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere 5.2: 2 h / -78 °C 5.3: 12 h / 20 °C 6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere 7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere 8.1: ammonia / methanol / 20 °C View Scheme |
methyl 4,4-difluorocyclohexane-1-carboxylate
(4,4-difluoro-1-methylcyclohexyl)methanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C View Scheme |
methyl 4,4-difluorocyclohexane-1-carboxylate
(4,4-difluoro-1-methylcyclohexyl)methyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C 1.2: 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C 3.1: triethylamine / dmap / 20 °C View Scheme |