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inquiry1‐cyclopropyl‐4,4,4‐trifluorobutane‐1,3‐dione
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation; | 98% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6S)-3-methyl-5-phenyl-6-propyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 97% B n/a |
Conditions | Yield |
---|---|
Stage #1: 2,3-dibromopropionic acid; acetyl chloride With copper(l) chloride; zinc In diethyl ether at 10 - 20℃; for 11h; Inert atmosphere; Stage #2: With Methylenetriphenylphosphorane In diethyl ether Temperature; Solvent; Concentration; | 96% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-methyl-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6S)-6-isobutyl-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 94% B n/a |
A
2-fluoro-1-tetralone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Selectfluor In water; acetonitrile at 20℃; | A 93% B n/a |
Conditions | Yield |
---|---|
With water; nitrile hydratase SP361 at 30℃; for 24h; in potassium phosphate buffer (pH = 7); | 92% |
With phosphoric acid; phosphorus pentoxide at 140℃; | |
With sodium hydroxide | |
With potassium hydroxide | |
In sodium hydroxide |
trans-Crotonaldehyde
Cyclopropanecarboxaldehyde
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
90% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-(methylsulfonyl)-1,3-diphenylhex-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6S)-3-methyl-6-(2-(methylsulfonyl)ethyl)-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 87% B n/a |
Conditions | Yield |
---|---|
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃; | 80% |
With Iron(III) nitrate nonahydrate; oxygen In acetonitrile at 25℃; under 760.051 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Schlenk technique; | 80% |
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water; acetone at 22℃; for 3h; Oxidation; | 71% |
With air at 21℃; for 2h; |
tert-butyl(cyclopropylmethoxy)dimethylsilane
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With ruthenium(IV) oxide; sodium periodate | 78% |
(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-5-((tertbutyldimethylsilyl)oxy)-1,3-diphenylpent-1-yn-3-yl cyclopropanecarboxylate
A
((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction; | A 52% B n/a |
Methyl 4-bromobutyrate
propargyl alcohol
A
methyl cyclopropylcarboxylate
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With lithium amide In diethyl ether for 4h; Heating; | A 20% B n/a |
Conditions | Yield |
---|---|
With potassium hydroxide at 100℃; Versetzen des Reaktionsgemisches mit Wasser; | |
With sodium hydroxide at 100℃; Versetzen des Reaktionsgemisches mit Wasser; |
Conditions | Yield |
---|---|
With potassium hypochlorite | |
With manganese(II) nitrate; oxygen; cobalt(II) nitrate In acetic acid at 100℃; for 6h; |
Conditions | Yield |
---|---|
With permanganate(VII) ion at 0 - 5℃; |
cyclopropanecarboxylic acid phenyl ester
A
phenol
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
at 360℃; |
Conditions | Yield |
---|---|
With carbon dioxide; n-pentylsodium |
cyclopropanecarboxylic anhydride
A
propene
B
1,2-propanediene
C
butadiene monoxide
D
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
at 666.9℃; |
2-Cyclopropyl-4,4-dimethyl-4,5-dihydro-oxazole
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hypochlorite; tetra(n-butyl)ammonium hydrogensulfate 1.) ethyl acetate, water, room temp.; 2.) CH3OH, 5 h, room temp.; Yield given. Multistep reaction; |
cyclopropanecarboxylic acid chloride
A
1-chlorocyclopropane-1-carboxylic acid
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With N-chloro-succinimide; sodium hydrogencarbonate 1.) 135 deg C, 1.5 h, 2.) acetone, 0 deg C; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate; copper(II) sulfate In benzene Yield given; |
cyclopropylmethyl methyl ether
A
methyl cyclopropylcarboxylate
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With ruthenium tetroxide In water; acetone at 30℃; |
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
A
alprenolol
B
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
Conditions | Yield |
---|---|
With water at 37℃; pH=1 - 12; Kinetics; Further Variations:; Reagents; Hydrolysis; |
Conditions | Yield |
---|---|
With thionyl chloride In toluene Heating; | 100% |
With thionyl chloride for 3h; Heating; | 95% |
With thionyl chloride for 4h; Heating; | 88% |
4-(hexyn-1-yl)anisole
cyclopropanecarboxylic acid
(E)-2-iodo-1-(4-methoxyphenyl)hex-1-en-1-yl cyclopropanecarboxylate
Conditions | Yield |
---|---|
With N-iodo-succinimide In 1,2-dichloro-ethane at 70℃; for 1h; stereoselective reaction; | 100% |
2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-amine 1',1'-dioxide
cyclopropanecarboxylic acid
N-{2-cyclopropyl-1-[(4-fluorophenyl)sulfonyl]-1',1'-dioxido-1,2,2',3',5',6'-hexahydrospiro[indole-3,4'-thiopyran]-5-yl}cyclopropanecarboxamide
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 100% |
1,2,3-Benzotriazole
cyclopropanecarboxylic acid
(1H-benzo[d][1,2,3]triazol-1-yl)(cyclopropyl)methanone
Conditions | Yield |
---|---|
Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h; Stage #2: cyclopropanecarboxylic acid In dichloromethane at 20℃; for 4h; | 100% |
With thionyl chloride at 0 - 20℃; Reagent/catalyst; | 70% |
With thionyl chloride In dichloromethane at 20℃; |
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 100% |
(piperidin-4-yl)carbamic acid tert-butyl ester
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
Stage #1: cyclopropanecarboxylic acid With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (piperidin-4-yl)carbamic acid tert-butyl ester In dichloromethane at 20℃; Inert atmosphere; | 100% |
Stage #1: cyclopropanecarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: (piperidin-4-yl)carbamic acid tert-butyl ester In dichloromethane at 20℃; Inert atmosphere; | 100% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 12h; |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 100% |
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 18h; | 100% |
Conditions | Yield |
---|---|
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | 99% |
With nonane; 9-borabicyclo; lithium 9-boratabicyclo In tetrahydrofuran for 1h; Ambient temperature; | 85% |
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 1 h; Yield given. Multistep reaction; | |
With ThxBHO-s-Bu In tetrahydrofuran at 25℃; for 96h; Yield given; |
Conditions | Yield |
---|---|
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve; | 99% |
5-bromoindoline
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With trimethylsilyl iodide for 96h; | 98% |
cyclopropanecarboxylic acid
cyclopropanecarboxylic acid benzyl ester
Conditions | Yield |
---|---|
With triethylamine In various solvent(s) at 83℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid In ethanol | 98% |
styrene
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With N-iodo-succinimide In dichloromethane at 20 - 22℃; for 0.25h; regioselective reaction; | 98% |
tert-butyl 1,4-diazepine-1-carboxylate
cyclopropanecarboxylic acid
tert-butyl 4-(cyclopropylaminocarbamoyl)-1,4-N-cycloheptane-1-carboxylate
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere; | 98% |
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; | 98% |
Cyclohexanethiol
cyclopropanecarboxylic acid
Cyclopropanecarbothioic acid S-cyclohexyl ester
Conditions | Yield |
---|---|
With pyridine; O-phenyl phosphorodichloridate In 1,2-dimethoxyethane for 16h; Ambient temperature; | 97% |
1,1'-carbonyldiimidazole
cyclopropanecarboxylic acid
1-cyclopropcarbonylimidazole
Conditions | Yield |
---|---|
at 20℃; for 20h; | 96% |
at 20℃; for 20h; | 96% |
In tetrahydrofuran Heating; |
ethyl 2-(2-hydroxyphenyl)acetate
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Steglich Esterification; Inert atmosphere; | 96% |
tri-p-fluorophenylstibine
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In diethyl ether at 20℃; for 24h; | 96% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate In isopropyl alcohol at 83℃; for 24h; Microwave irradiation; | 96% |
cyclopropanecarboxylic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere; | 96% |
levonorgestrel
cyclopropanecarboxylic acid
D-(-)-norgestrel 17β-cyclopropanecarboxylate
Conditions | Yield |
---|---|
With sodium carbonate; trifluoroacetic anhydride In benzene for 1h; Ambient temperature; | 95.9% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In tert-butyl methyl ether at 0 - 50℃; for 24h; | 95% |
With lithium aluminium tetrahydride | 83% |
With lithium aluminium tetrahydride | 67% |
benzyl alcohol
cyclopropanecarboxylic acid
cyclopropanecarboxylic acid benzyl ester
Conditions | Yield |
---|---|
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 17h; Heating; | 95% |
With 2,5-dimethylpyridine; 4,5-dichloro-1,2,3-dithiazolium chloride In dichloromethane 1) -78 deg C, 2 h, 2) to room temperature, 12 h; | 76% |
With tributyl-amine; 2-chloro-1-ethylpyridinium tetrafluoroborate In dichloromethane Ambient temperature; |
6-methoxy-9-(propa-1,2-dien-1-yl)-9H-purine
cyclopropanecarboxylic acid
(E)-3-(6-methoxy-9H-purin-9-yl)allyl cyclopropanecarboxylate
Conditions | Yield |
---|---|
With silver carbonate In acetonitrile at 80℃; for 8h; chemoselective reaction; | 95% |
3-bromoaniline
cyclopropanecarboxylic acid
N-(3-bromophenyl)cyclopropanecarboxamide
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 95% |
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