2-(2,4,5-trifluorophenyl)acetyl chloride
bromoacetic acid methyl ester
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: bromoacetic acid methyl ester With iodine; magnesium In tetrahydrofuran at 45 - 50℃; Inert atmosphere; Stage #2: 2-(2,4,5-trifluorophenyl)acetyl chloride With copper(l) iodide In tetrahydrofuran at -20 - 5℃; Grignard Reaction; Inert atmosphere; | 91% |
methanol
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
In toluene for 3h; Heating; | 88.7% |
at 60 - 63℃; |
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
With methanol at 60 - 63℃; | 85% |
In methanol Reflux; |
monomethyl monopotassium malonate
(2,4,5-trifluorophenyl)acetic acid
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (2,4,5-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In acetonitrile for 3.5h; Stage #2: monomethyl monopotassium malonate With triethylamine; magnesium chloride In acetonitrile at 50℃; for 8h; Stage #3: In acetonitrile at 30℃; for 26h; | 84% |
Stage #1: monomethyl monopotassium malonate With triethylamine In acetonitrile at 30 - 50℃; for 8.3h; Stage #2: (2,4,5-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 30℃; for 3.5h; | 83% |
Stage #1: monomethyl monopotassium malonate With triethylamine; magnesium chloride In acetonitrile at 30 - 50℃; Inert atmosphere; Stage #2: (2,4,5-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In acetonitrile at 30℃; for 5.5h; Inert atmosphere; | 83% |
(2,4,5-trifluorophenyl)acetic acid
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (2,4,5-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; Stage #2: magnesium monomethyl malonate In tetrahydrofuran at 20℃; for 24h; | 77.3% |
monomethyl monopotassium malonate
(2,4,5-trifluorophenyl)acetic acid
A
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (2,4,5-trifluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In acetonitrile for 3.5h; Stage #2: monomethyl monopotassium malonate With triethylamine; magnesium chloride In acetonitrile at 50℃; for 8h; Stage #3: In acetonitrile at 30℃; for 26h; |
(2,4,5-trifluorophenyl)acetic acid
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / N,N-dimethylaminopyridine; N,N-diisopropylethylamine; trimethylacetylchloride / acetonitrile / 3 h / 45 °C 2: 88.7 percent / toluene / 3 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: oxalic acid / dichloromethane; N,N-dimethyl-formamide / 25 - 30 °C 1.2: -5 °C 2.1: methanol / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 25 - 30 °C 1.2: 6 h / 50 - 55 °C 2.1: 60 - 63 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: thionyl chloride / chloroform / 2 h / 0 - 30 °C 2.1: magnesium; iodine / tetrahydrofuran / 45 - 50 °C / Inert atmosphere 2.2: -20 - 5 °C / Inert atmosphere View Scheme |
methanol
sodium 1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-2-(2,4,5-trifluorophenyl)ethanolate
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
With methanesulfonic acid Reflux; |
methyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid; acetic acid at 25 - 30℃; for 24h; |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With acetic acid In methanol Reflux; Large scale; | 98.5% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-methyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate
Conditions | Yield |
---|---|
With [Ir(H)2((R)-N-((1,3-dithian-2-yl)methyl)-7'-(bis(3,5-di-tert-butylphenyl)phosphanyl)-1,1'-spirobiindanyl-7-amine)Cl]; hydrogen; sodium hydroxide In methanol at 25 - 30℃; under 7600.51 Torr; for 2h; Reagent/catalyst; Autoclave; enantioselective reaction; | 98% |
Stage #1: 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In toluene at 0 - 5℃; Inert atmosphere; Stage #2: With methanol In toluene | |
With hydrogen; dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) In methanol; acetic acid at 70℃; under 3620.13 Torr; for 6h; Inert atmosphere; |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
With ammonium acetate In methanol for 7h; Heating; | 95% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
benzamide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 110℃; | 95% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
methyl 3-hydroxy-4-(2,4,5-trifluorophenyl)butanoate
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0℃; | 92% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybenzenebutanoic acid methyl ester
Conditions | Yield |
---|---|
With formic acid In methanol at 65℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; | 91.1% |
With hydrogen; (S)-BINAP RuCl2-triethylamine In methanol at 80 - 85℃; under 4413.43 - 4781.22 Torr; |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(2Z)-3-amino-4-(2,4,5-trifluorophenyl)but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
With ammonium acetate In methanol for 2h; Heating; | 91% |
With ammonium acetate In methanol for 4h; Reflux; | 89.6% |
With ammonium acetate In methanol at 60 - 63℃; | 85% |
With ammonium acetate In methanol at 60 - 63℃; |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With acetic acid In toluene for 3h; Reflux; | 87% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
3(S)-4-(2,4,5-trifluorophenyl)-3-hydroxybutanoic acid
Conditions | Yield |
---|---|
With dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II); hydrogen In methanol; acetic acid at 70℃; under 3620.13 Torr; Inert atmosphere; Autoclave; | 86% |
Multi-step reaction with 2 steps 1.1: hydrogen / dichloro[(S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]ruthenium(II) / acetic acid; methanol / 6 h / 70 °C / 3620.13 Torr / Inert atmosphere 2.1: sodium hydroxide; methanol / water / 1.5 h / 20 - 25 °C 2.2: 2 h / 10 - 15 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogen / (S)-BINAP RuCl2-triethylamine / methanol / 80 - 85 °C / 4413.43 - 4781.22 Torr 2: sodium hydroxide; water / 65 - 70 °C / Reflux View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
benzamide
Conditions | Yield |
---|---|
With diphenylammonium trifluoromethanesulfonate In toluene for 8h; Reflux; Green chemistry; stereoselective reaction; | 83% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
L-phenylglycine amide
Conditions | Yield |
---|---|
With acetic acid In ethanol at 40℃; for 16h; Solvent; Schiff Reaction; Inert atmosphere; | 80% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
N-benzyloxyamine
methyl (R)-3-(benzyloxyamino)-4-(2,4,5-trifluorophenyl)butanoate
Conditions | Yield |
---|---|
Stage #1: 4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester; N-benzyloxyamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: With (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; [(p-cymene)RuCl2]2 In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #3: With sodium cyanoborohydride; zinc(II) chloride In tetrahydrofuran for 0.333333h; Inert atmosphere; | 74% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Benzeneacetamide
Conditions | Yield |
---|---|
With diphenylammonium trifluoromethanesulfonate In toluene for 8h; Reflux; Green chemistry; stereoselective reaction; | 73% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
acetamide
(Z)-methyl 3-acetamido-4-(2,4,5-trifluorophenyl) but-2-enoate
Conditions | Yield |
---|---|
With diphenylammonium trifluoromethanesulfonate In toluene for 8h; Reflux; Green chemistry; stereoselective reaction; | 61% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
tert-butyl carbamate
3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 25℃; Molecular sieve; | 54.1% |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
methyl 3-amino-4-(2,4,5-trifluorophenyl)butanoate
Conditions | Yield |
---|---|
With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; | 52% |
Multi-step reaction with 2 steps 1.1: ammonium acetate / methanol / 60 - 63 °C 2.1: sulfuric acid / methanol / -10 - 0 °C 2.2: 2 h / -10 - 0 °C 2.3: pH 8 - 9 View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr View Scheme | |
Multi-step reaction with 2 steps 1: 91 percent / ammonium acetate / methanol / 2 h / Heating 2: [Rh(COD)Cl]2; chiral ferrocenyl ligand; H2 / 2,2,2-trifluoro-ethanol / 24 h / 40 °C / 10343 Torr View Scheme | |
Multi-step reaction with 4 steps 1.1: ammonium acetate / methanol / 60 - 63 °C 2.1: sulfuric acid / methanol / -10 - 0 °C 2.2: 2 h / -10 - 0 °C 2.3: pH 8 - 9 3.1: isopropyl alcohol / 3 h / 25 - 30 °C 4.1: sodium carbonate / water / pH 8 - 9 View Scheme | |
With transaminase; pyridoxal 5'-phosphate; isopropylamine In water; dimethyl sulfoxide at 45℃; for 8h; Enzymatic reaction; |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
3-(R)-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyric acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 91 percent / ammonium acetate / methanol / 2 h / Heating 2: 75 percent / [Rh(COD)Cl]2; chiral ferrocenyl ligand; H2 / methanol / 24 h / 30 °C / 4654.33 Torr View Scheme | |
Multi-step reaction with 3 steps 1: acetic acid / methanol / Reflux; Large scale 2: boron trifluoride diethyl etherate; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / -78 - 0 °C / Large scale 3: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 25 °C View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-[3-oxo-3-pyrazolidin-1-yl-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C 5: 47 percent / EDCI; triethylamine / CH2Cl2 / 1 h / 20 °C View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-[3-oxo-3-(tetrahydropyridazin-1-yl)-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C 5: 66 percent / EDCI; triethylamine / CH2Cl2 / 12 h / 20 °C View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-[3-[1,2]diazepan-1-yl-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C 5: 90 percent / EDCI; triethylamine / CH2Cl2 / 12 h / 20 °C View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C 5: 47 percent / EDCI; triethylamine / CH2Cl2 / 1 h / 20 °C 6: 99 percent / HCl / ethyl acetate; dioxane / 16 h / 20 °C View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-[3-(2-benzoylcarbamoylpyrazolidin-1-yl)-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C 5: 47 percent / EDCI; triethylamine / CH2Cl2 / 1 h / 20 °C 6: 85 percent / CH2Cl2 / 2 h / 20 °C View Scheme |
4-(2,4,5-trifluoro-phenyl)-3-oxo-butyric acid methyl ester
(R)-[3-oxo-3-(2-(toluene-4-sulfonyl)pyrazolidin-1-yl)-1-(2,4,5-trifluorbenzyl)propyl]carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 95 percent / ammonium acetate / methanol / 7 h / Heating 2: 68 percent / H2; (R) chiral ferrocenyl derivative / chloro(1,5-cyclooctadiene)rhodium(I) dimer / 2,2,2-trifluoro-ethanol / 40 h / 50 °C / 5171.62 Torr 3: 93 percent / CH2Cl2 / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 20 °C 5: 47 percent / EDCI; triethylamine / CH2Cl2 / 1 h / 20 °C 6: 76 percent / Et3N / CH2Cl2 / 2 h / 20 °C View Scheme |
The Methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate, with the CAS registry number 769195-26-8, has the molecular formula C11H9F3O3. In addition, this chemical's molecular weight is 246.18. Its systematic name is called methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate.
Physical properties of Methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate: (1)ACD/LogP: 1.68; (2)ACD/LogD (pH 5.5): 1.678; (3)ACD/LogD (pH 7.4): 1.676; (4)ACD/BCF (pH 5.5): 11.092; (5)ACD/BCF (pH 7.4): 11.061; (6)ACD/KOC (pH 5.5): 194.819; (7)ACD/KOC (pH 7.4): 194.28; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.469; (11)Molar Refractivity: 51.487 cm3; (12)Molar Volume: 185.002 cm3; (13)Surface Tension: 36.393 dyne/cm; (14)Density: 1.331 g/cm3; (15)Flash Point: 115.458 °C; (16)Enthalpy of Vaporization: 51.16 kJ/mol; (17)Boiling Point: 273.265 °C at 760 mmHg; (18)Vapour Pressure: 0.006 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: COC(=O)CC(=O)Cc1cc(c(cc1F)F)F
(2)InChI: InChI=1/C11H9F3O3/c1-17-11(16)4-7(15)2-6-3-9(13)10(14)5-8(6)12/h3,5H,2,4H2,1H3
(3)InChIKey: XDQLWVSUKUDAEO-UHFFFAOYAS
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