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[ CAS No. 6223-83-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 6223-83-2
Chemical Structure| 6223-83-2
Chemical Structure| 6223-83-2
Structure of 6223-83-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 6223-83-2 ]

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Alternatived Products of [ 6223-83-2 ]

Product Details of [ 6223-83-2 ]

CAS No. :6223-83-2 MDL No. :MFCD00001145
Formula : C14H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :AFQYQSWTVCNJQT-UHFFFAOYSA-N
M.W : 224.21 Pubchem ID :80361
Synonyms :

Calculated chemistry of [ 6223-83-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.27
TPSA : 54.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.6
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 2.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.108 mg/ml ; 0.000481 mol/l
Class : Soluble
Log S (Ali) : -3.38
Solubility : 0.0933 mg/ml ; 0.000416 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.46
Solubility : 0.00785 mg/ml ; 0.000035 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.23

Safety of [ 6223-83-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6223-83-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6223-83-2 ]

[ 6223-83-2 ] Synthesis Path-Downstream   1~96

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YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; In water; at 135 - 145℃; for 1.2h;Heating / reflux; This example describes the preparation of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile, for convenience to be designated ETM-2. [0094] A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) and 100 g of diphenic acid (0.41 mole, commercially obtained from Acros Fisher Scientific Company Inc., Hanover Park, Ill.) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and a reflux condenser. Using a heating mantle, the flask was heated to 135-145 C. for 12 minutes, and then cooled to room temperature. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and was boiled gently for one hour. A yellow solid was filtered out hot, washed with hot water until the pH of the wash-water was neutral, and was air-dried overnight. The yellow solid was fluorenone-4-carboxylic acid. The yield was 75 g (80%). The product was then characterized. The melting point (m.p.) was found to be 223-224 C. A 1H-NMR spectrum of fluorenone-4-carboxylic acid was obtained in d6-DMSO solvent with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=7.39-7.50 (m, 2H); delta=7.79-7.70 (q, 2H); delta=7.74-7.85 (d, 1H); delta=7.88-8.00 (d, 1H); and delta=8.18-8.30 (d, 1H), where d is doublet, t is triplet, m is multiplet; dd is double doublet, q is quintet. [0095] A 70 g (0.312 mole) quantity of fluorenone-4-carboxylic acid, 480 g (6.5 mole) of n-butanol (commercially obtained from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of Toluene and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation and refluxing, the solution was refluxed for 5 hours, during which 6 g of water were collected in the Dean Stark apparatus. The flask was cooled to room temperature. The solvents were evaporated and the residue was added, with agitation, to 4-liter of a 3% sodium bicarbonate aqueous solution. The solid was filtered off, washed with water until the pH of the wash-water was neutral, and dried in the hood overnight. The product was n-butyl fluorenone-4-carboxylate ester. The yield was 70 g (80%). A 1H-NMR spectrum of n-butyl fluorenone-4-carboxylate ester was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.87-1.09 (t, 3H); delta=1.42-1.70 (m, 2H); delta=1.75-1.88 (q, 2H); delta=4.26-4.64 (t, 2H); delta=7.29-7.45 (m, 2H); delta=7.46-7.58 (m, 1H); delta=7.60-7.68 (dd, 1H); delta=7.75-7.82 (dd, 1H); delta=7.90-8.00 (dd, 1H); delta=8.25-8.35 (dd, 1H). [0096] A 70 g (0.25 mole) quantity of n-butyl fluorenone-4-carboxylate ester, 750 ml of absolute methanol, 37 g (0.55 mole) of malononitrile (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.), 20 drops of piperidine (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) were added to a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. The solution was refluxed for 8 hours and the flask was cooled to room temperature. The orange crude product was filtered, washed twice with 70 ml of methanol and once with 150 ml of water, and dried overnight in the hood. This orange crude product was recrystalized from a mixture of 600 ml of acetone and 300 ml of methanol using activated charcoal. The flask was placed at 0 C. for 16 hours. The crystals were filtered and dried in a vacuum oven at 50 C. for 6 hours to obtain 60 g of pure (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile. The melting point (m.p.) of the solid was found to be 99-100 C. A 1H-NMR spectrum of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.74-1.16 (t, 3H); delta=1.38-1.72 (m, 2H); delta=1.70-1.90 (q, 2H); delta=4.29-4.55 (t, 2H); delta=7.31-7.43 (m, 2H); delta=7.45-7.58 (m, 1H); delta=7.81-7.91 (dd, 1H); delta=8.15-8.25 (dd, 1H); delta=8.42-8.52 (dd, 1H); delta=8.56-8.66 (dd, 1H)
80% With sulfuric acid; In water; at 20 - 145℃; for 1.2h;Heating / reflux; A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) and 100 g of diphenic acid (0.41 mole, commercially obtained from Acros Fisher Scientific Company Inc., Hanover Park, Ill.) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and a reflux condenser. Using a heating mantle, the flask was heated to 135-145 C. for 12 minutes, and then cooled to room temperature. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and was boiled gently for one hour. A yellow solid was filtered out hot, washed with hot water until the pH of the wash-water was neutral, and was air-dried overnight. The yellow solid was fluorenone-4-carboxylic acid. The yield was 75 g (80%). The product was then characterized. The melting point (m.p.) was found to be 223-224 C. A 1H-NMR spectrum of fluorenone-4-carboxylic acid was obtained in d6-DMSO solvent with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=7.39-7.50 (m, 2H); delta=7.79-7.70 (q, 2H); delta=7.74-7.85 (d, 1H); delta=7.88-8.00 (d, 1H); and delta=8.18-8.30 (d, 1H), where d is doublet, t is triplet, m is multiplet; dd is double doublet, q is quintet. [0089] A 70 g (0.312 mole) quantity of fluorenone-4-carboxylic acid, 480 g (6.5 mole) of n-butanol (commercially obtained from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of toluene and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation and refluxing, the solution was refluxed for 5 hours, during which 6 g of water were collected in the Dean Stark apparatus. The flask was cooled to room temperature. The solvents were evaporated and the residue was added, with agitation, to 4-liter of a 3% sodium bicarbonate aqueous solution. The solid was filtered off, washed with water until the pH of the wash-water was neutral, and dried in the hood overnight. The product was n-butyl fluorenone-4-carboxylate ester. The yield was 70 g (80%). A 1H-NMR spectrum of n-butyl fluorenone-4-carboxylate ester was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.87-1.09 (t, 3H); delta=1.42-1.70 (m, 2H); delta=1.75-1.88 (q, 2H); delta=4.26-4.64 (t, 2H); delta=7.29-7.45 (m, 2H); delta=7.46-7.58 (m, 1H); delta=7.60-7.68 (dd, 1H); delta=7.75-7.82 (dd, 1H); delta=7.90-8.00 (dd, 1H); delta=8.25-8.35 (dd, 1H). [0090] A 70 g (0.25 mole) quantity of n-butyl fluorenone-4-carboxylate ester, 750 ml of absolute methanol, 37 g (0.55 mole) of malononitrile (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.), 20 drops of piperidine (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) were added to a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. The solution was refluxed for 8 hours and the flask was cooled to room temperature. The orange crude product was filtered, washed twice with 70 ml of methanol and once with 150 ml of water, and dried overnight in the hood. This orange crude product was recrystalized from a mixture of 600 ml of acetone and 300 ml of methanol using activated charcoal. The flask was placed at 0 C. for 16 hours. The crystals were filtered and dried in a vacuum oven at 50 C. for 6 hours to obtain 60 g of pure (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile. The melting point (m.p.) of the solid was found to be 99-100 C. A 1H-NMR spectrum of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.74-1.16 (t, 3H); delta=1.38-1.72 (m, 2H); delta=1.70-1.90 (q, 2H); delta=4.29-4.55 (t, 2H); delta=7.31-7.43 (m, 2H); delta=7.45-7.58 (m, 1H); delta=7.81-7.91 (dd, 1H); delta=8.15-8.25 (dd, 1H); delta=8.42-8.52 (dd, 1H); delta=8.56-8.66 (dd, 1H).
With sulfuric acid; at 140℃; for 0.333333h; To 200 mL of concentrated H2SO4, was added biphenic acid (70 g, 0.289 M). The resulting mixture was heated to 140 C for 20 minutes, cooled, poured into ice-water (2 L ) to give a suspension. The mixture was filtered, washed with water, dried at 50C under vacuum to afford 56 g of compound 11 as greenish yellow solid. 1H NMR (400 MHz, DMSO-d6) delta: 7.45 (2H, m), 7.65 (2H, q), 7.8 (1H, d), 7.95 (1H, d), 8.25 (1H, d).
With concentrated sulfuric acid; In water; Preparation of (4-n-Butoxycarbonyl-9-fluorenylidene) Malononitrile A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, commercially obtained from Sigma-Aldrich, Milwaukee, WI) and 100 g of diphenic acid (0.41 mole, commercially obtained from Acros Fisher Scientific Company Inc., Hanover Park, IL) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and a reflux condenser. Using a heating mantle, the flask was heated to 135-145 C for 12 minutes, and then cooled to room temperature. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and was boiled gently for one hour. A yellow solid was filtered out hot, washed with hot water until the pH of the wash-water was neutral, and was air-dried overnight. The yellow solid was fluorenone-4-carboxylic acid. The yield was 75 g (80%). The product was then characterized. The melting point (m.p.) was found to be 223-224 C. A 1H-NMR spectrum of fluorenone-4-carboxylic acid was obtained in d6-DMSO solvent with a 300 MHz NMR from Bruker Instrument.
With sulfuric acid; In water; Example 2 Preparation of an Electron Transport Compound This example describes the preparation of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile. A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) and 100 g of diphenic acid (0.41 mole, commercially obtained from Acros Fisher Scientific Company Inc., Hanover Park, Ill.) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and a reflux condenser. Using a heating mantle, the flask was heated to 135-145 C. for 12 minutes, and then cooled to room temperature. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and was boiled gently for one hour. A yellow solid was filtered out hot, washed with hot water until the pH of the wash-water was neutral, and dried in the air overnight. The yellow solid was fluorenone-4-carboxylic acid. The yield was 75 g (80%). The product was then characterized. The melting point (m.p.) was found to be 223-224 C. A 1H-NMR spectrum of fluorenone-4-carboxylic acid was obtained in d6-DMSO solvent with a 300 MHz NMR from Bruker Instrument.

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  • [ 1066-26-8 ]
  • 9-ethynyl-9-hydroxy-fluorene-4-carboxylic acid [ No CAS ]
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  • [ 75-08-1 ]
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  • [ 109-77-3 ]
  • [ 36232-49-2 ]
YieldReaction ConditionsOperation in experiment
9.01 g With piperidine; In methanol; for 48.0h;Reflux; A mixture of 9.31 g (0.0415 mole) of fluorenone-4-carboxylic acid and 75 mL of absolute methanol was magnetically stirred and heated to reflux temperature in a round-bottomed flask fitted with a reflux condenser. Subsequently, there was added to the flask 8.23 g (0.125 mole) of malononitrile and 2 drops of piperidine. The mixture was then heated under reflux for 48 hours. The solid product 4-carboxy-9-fluorenylidene malononitrile, was collected by suction filtration, and purified by stirring in 50 mL of boiling methanol for 15 min, followed by filtration and washing successively with 20 mL of methanol. The product was dried under vacuum at 65 C. for 12 hours and weighed 9.01 g.
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  • [ 6223-83-2 ]
  • [ 42523-41-1 ]
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  • [ 110-89-4 ]
  • n-butyl 9-fluorenone-4-carboxylate ester [ No CAS ]
  • [ 6223-83-2 ]
  • [ 109-77-3 ]
  • [ 71-36-3 ]
  • [ 93376-18-2 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; sodium hydrogencarbonate; In methanol; water; acetone; toluene; Preparation Example 5 Preparation of Compound (26) The following is a description of the preparation of a dicyanofluorene-based compound Compound (26) to be used as an ETM in Comparative Example 1. A mixture of 70 g (0.312 mole) of <strong>[6223-83-2]9-fluorenone-4-carboxylic acid</strong> (from Sigma-Aldrich, Milwaukee, Wis.), 480 g (6.5 mole) of n-butanol (manufactured from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of toluene, and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation, the solution was refluxed for 5 hours, during which time about 6 g of water was collected in the Dean Stark apparatus. After refluxing, the flask was cooled to room temperature. The solvents were evaporated and the residue was added with agitation to 4-liter of a 3% aqueous solution of sodium bicarbonate. The solid was filtered off, washed with water until the pH of the washed water was neutral, and dried under a hood overnight. The product was n-butyl 9-fluorenone-4-carboxylate ester. The yield was 70 g (80%). A mixture of 70 g (0.25 mole) of n-butyl 9-fluorenone-4-carboxylate ester, 750 ml of absolute methanol, 37 g (0.55 mole) of malononitrile (from Sigma-Aldrich, Milwaukee, Wis.), 20 drops of piperidine (from Sigma-Aldrich, Milwaukee, Wis.) was added to a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. The solution was refluxed for 8 hours and the flask was cooled to room temperature. The orange crude product was filtered, washed twice with 70 ml of methanol and once with 150 ml of water, and dried overnight in a hood. This orange crude product was recrystallized from a mixture of 600 ml of acetone and 300 ml of methanol using activated charcoal. The flask was placed at 0 C. for 16 hours. The crystals formed were filtered and dried in a vacuum oven at 50 C. for 6 hours to obtain 60 g of pure (4-n-butoxycarbonyl-9-fluorenylidene)malononitrile (Compound (26)).
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  • [ 6223-83-2 ]
  • 5-chloro-2-[(9-oxo-9<i>H</i>-fluorene-4-carbonyl)-amino]-benzoic acid [ No CAS ]
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  • [ 6223-83-2 ]
  • [ 295801-31-9 ]
  • 25
  • [ 6223-83-2 ]
  • N-(2-(β-cyanoethyl-N,N'-diisopropylphosphino)ethyl)-9-fluorenone-4-carboxamide [ No CAS ]
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  • [ 6223-83-2 ]
  • [ 4269-20-9 ]
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  • [ 212255-38-4 ]
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  • [ 212255-37-3 ]
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  • [ 6223-83-2 ]
  • (Z)-4-cyano-9-(4'-methoxyphenylmethylidene)fluorene [ No CAS ]
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  • [ 6223-83-2 ]
  • (E)-4-cyano-9-(4'-methoxyphenylmethylidene)fluorene [ No CAS ]
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  • [ 6223-83-2 ]
  • (Z)-4-cyano-9-[4-(trifluoromethyl)phenylmethylidene]fluorene [ No CAS ]
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  • [ 6223-83-2 ]
  • (E)-4-cyano-9-[4-(trifluoromethyl)phenylmethylidene]fluorene [ No CAS ]
  • 36
  • [ 6223-83-2 ]
  • 9-(triphenyl-λ5-phosphanylidene)-9<i>H</i>-fluorene-4-carbonitrile [ No CAS ]
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  • [ 6223-83-2 ]
  • 9-(4-cyanofluorenyl)triphenylphosphonium chloride [ No CAS ]
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  • [ 6223-83-2 ]
  • [ 95303-01-8 ]
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  • [ 6223-83-2 ]
  • N-(t-Butoxycarbonyl)-L-valine <4'-(2,4,5-Trichlorophenyloxycarbonyl)fluorene-9'-yl>-methyl Ester [ No CAS ]
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  • [ 6223-83-2 ]
  • [ 93619-93-3 ]
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  • [ 6223-83-2 ]
  • 9-Oxo-9H-fluorene-4-carboxylic acid octadecyl ester [ No CAS ]
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  • [ 6223-83-2 ]
  • 9-Oxo-9H-fluorene-4-carboxylic acid di-undec-10-enyl-amide [ No CAS ]
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  • [ 6223-83-2 ]
  • [ 124614-89-7 ]
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  • [ 6223-83-2 ]
  • [ 124614-86-4 ]
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  • [ 6223-83-2 ]
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  • [ 6223-83-2 ]
  • 9-[(E)-Butylimino]-9H-fluorene-4-carboxylic acid di-undec-10-enyl-amide [ No CAS ]
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  • [ 6223-83-2 ]
  • [ 124614-88-6 ]
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  • [ 6223-83-2 ]
  • [ 124614-92-2 ]
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  • [ 6223-83-2 ]
  • 9-Oxo-9H-fluorene-4-carboxylic acid dioctadecylamide [ No CAS ]
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  • [ 6223-83-2 ]
  • 9-[(E)-Butylimino]-9H-fluorene-4-carboxylic acid dioctadecylamide [ No CAS ]
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  • [ 6223-83-2 ]
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  • [ 4269-19-6 ]
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  • [ 6223-83-2 ]
  • 9,9-bis-(4-acetoxy-phenyl)-fluorene-4-carboxylic acid [ No CAS ]
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  • [ 1986-00-1 ]
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  • [ 28147-35-5 ]
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  • [ 71-36-3 ]
  • [ 93519-65-4 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; In toluene; for 5.0h;Heating / reflux; This example describes the preparation of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile, for convenience to be designated ETM-2. [0094] A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) and 100 g of diphenic acid (0.41 mole, commercially obtained from Acros Fisher Scientific Company Inc., Hanover Park, Ill.) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and a reflux condenser. Using a heating mantle, the flask was heated to 135-145 C. for 12 minutes, and then cooled to room temperature. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and was boiled gently for one hour. A yellow solid was filtered out hot, washed with hot water until the pH of the wash-water was neutral, and was air-dried overnight. The yellow solid was fluorenone-4-carboxylic acid. The yield was 75 g (80%). The product was then characterized. The melting point (m.p.) was found to be 223-224 C. A 1H-NMR spectrum of fluorenone-4-carboxylic acid was obtained in d6-DMSO solvent with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=7.39-7.50 (m, 2H); delta=7.79-7.70 (q, 2H); delta=7.74-7.85 (d, 1H); delta=7.88-8.00 (d, 1H); and delta=8.18-8.30 (d, 1H), where d is doublet, t is triplet, m is multiplet; dd is double doublet, q is quintet. [0095] A 70 g (0.312 mole) quantity of fluorenone-4-carboxylic acid, 480 g (6.5 mole) of n-butanol (commercially obtained from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of Toluene and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation and refluxing, the solution was refluxed for 5 hours, during which 6 g of water were collected in the Dean Stark apparatus. The flask was cooled to room temperature. The solvents were evaporated and the residue was added, with agitation, to 4-liter of a 3% sodium bicarbonate aqueous solution. The solid was filtered off, washed with water until the pH of the wash-water was neutral, and dried in the hood overnight. The product was n-butyl fluorenone-4-carboxylate ester. The yield was 70 g (80%). A 1H-NMR spectrum of n-butyl fluorenone-4-carboxylate ester was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.87-1.09 (t, 3H); delta=1.42-1.70 (m, 2H); delta=1.75-1.88 (q, 2H); delta=4.26-4.64 (t, 2H); delta=7.29-7.45 (m, 2H); delta=7.46-7.58 (m, 1H); delta=7.60-7.68 (dd, 1H); delta=7.75-7.82 (dd, 1H); delta=7.90-8.00 (dd, 1H); delta=8.25-8.35 (dd, 1H). [0096] A 70 g (0.25 mole) quantity of n-butyl fluorenone-4-carboxylate ester, 750 ml of absolute methanol, 37 g (0.55 mole) of malononitrile (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.), 20 drops of piperidine (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) were added to a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. The solution was refluxed for 8 hours and the flask was cooled to room temperature. The orange crude product was filtered, washed twice with 70 ml of methanol and once with 150 ml of water, and dried overnight in the hood. This orange crude product was recrystalized from a mixture of 600 ml of acetone and 300 ml of methanol using activated charcoal. The flask was placed at 0 C. for 16 hours. The crystals were filtered and dried in a vacuum oven at 50 C. for 6 hours to obtain 60 g of pure (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile. The melting point (m.p.) of the solid was found to be 99-100 C. A 1H-NMR spectrum of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.74-1.16 (t, 3H); delta=1.38-1.72 (m, 2H); delta=1.70-1.90 (q, 2H); delta=4.29-4.55 (t, 2H); delta=7.31-7.43 (m, 2H); delta=7.45-7.58 (m, 1H); delta=7.81-7.91 (dd, 1H); delta=8.15-8.25 (dd, 1H); delta=8.42-8.52 (dd, 1H); delta=8.56-8.66 (dd, 1H)
80% With sulfuric acid; In toluene; for 5.0h;Heating / reflux; A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) and 100 g of diphenic acid (0.41 mole, commercially obtained from Acros Fisher Scientific Company Inc., Hanover Park, Ill.) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and a reflux condenser. Using a heating mantle, the flask was heated to 135-145 C. for 12 minutes, and then cooled to room temperature. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and was boiled gently for one hour. A yellow solid was filtered out hot, washed with hot water until the pH of the wash-water was neutral, and was air-dried overnight. The yellow solid was fluorenone-4-carboxylic acid. The yield was 75 g (80%). The product was then characterized. The melting point (m.p.) was found to be 223-224 C. A 1H-NMR spectrum of fluorenone-4-carboxylic acid was obtained in d6-DMSO solvent with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=7.39-7.50 (m, 2H); delta=7.79-7.70 (q, 2H); delta=7.74-7.85 (d, 1H); delta=7.88-8.00 (d, 1H); and delta=8.18-8.30 (d, 1H), where d is doublet, t is triplet, m is multiplet; dd is double doublet, q is quintet. [0089] A 70 g (0.312 mole) quantity of fluorenone-4-carboxylic acid, 480 g (6.5 mole) of n-butanol (commercially obtained from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of toluene and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation and refluxing, the solution was refluxed for 5 hours, during which 6 g of water were collected in the Dean Stark apparatus. The flask was cooled to room temperature. The solvents were evaporated and the residue was added, with agitation, to 4-liter of a 3% sodium bicarbonate aqueous solution. The solid was filtered off, washed with water until the pH of the wash-water was neutral, and dried in the hood overnight. The product was n-butyl fluorenone-4-carboxylate ester. The yield was 70 g (80%). A 1H-NMR spectrum of n-butyl fluorenone-4-carboxylate ester was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.87-1.09 (t, 3H); delta=1.42-1.70 (m, 2H); delta=1.75-1.88 (q, 2H); delta=4.26-4.64 (t, 2H); delta=7.29-7.45 (m, 2H); delta=7.46-7.58 (m, 1H); delta=7.60-7.68 (dd, 1H); delta=7.75-7.82 (dd, 1H); delta=7.90-8.00 (dd, 1H); delta=8.25-8.35 (dd, 1H). [0090] A 70 g (0.25 mole) quantity of n-butyl fluorenone-4-carboxylate ester, 750 ml of absolute methanol, 37 g (0.55 mole) of malononitrile (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.), 20 drops of piperidine (commercially obtained from Sigma-Aldrich, Milwaukee, Wis.) were added to a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer and a reflux condenser. The solution was refluxed for 8 hours and the flask was cooled to room temperature. The orange crude product was filtered, washed twice with 70 ml of methanol and once with 150 ml of water, and dried overnight in the hood. This orange crude product was recrystalized from a mixture of 600 ml of acetone and 300 ml of methanol using activated charcoal. The flask was placed at 0 C. for 16 hours. The crystals were filtered and dried in a vacuum oven at 50 C. for 6 hours to obtain 60 g of pure (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile. The melting point (m.p.) of the solid was found to be 99-100 C. A 1H-NMR spectrum of (4-n-butoxycarbonyl-9-fluorenylidene) malononitrile was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The peaks were found at (ppm) delta=0.74-1.16 (t, 3H); delta=1.38-1.72 (m, 2H); delta=1.70-1.90 (q, 2H); delta=4.29-4.55 (t, 2H); delta=7.31-7.43 (m, 2H); delta=7.45-7.58 (m, 1H); delta=7.81-7.91 (dd, 1H); delta=8.15-8.25 (dd, 1H); delta=8.42-8.52 (dd, 1H); delta=8.56-8.66 (dd, 1H).
With sulfuric acid; sodium hydrogencarbonate; In water; toluene; A mixture of <strong>[6223-83-2]9-fluorenone-4-carboxylic acid</strong> (70 g, 0.312 mole, from Sigma-Aldrich, Milwaukee, WI), n-butanol (480 g, 6.5 mole, from Fisher Scientific Company Inc., Hanover Park, IL), toluene (1000 ml), and concentrated sulfuric acid (4 ml) was added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation, the solution was refluxed for 5 hours, during which time ~ 6 g of water were collected in the Dean Stark apparatus. After refluxing, the flask was cooled to room temperature. The solvents were evaporated and the residue was added with agitation to 4-liter of a 3% aqueous solution of sodium bicarbonate. The solid was filtered off, washed with water until the pH of the washed water was neutral, and dried in the hood overnight. The product was n-butyl fluorenone-4-carboxylate ester. The yield was 70 g (80%). A 1H-NMR spectrum of n-butyl fluorenone-4-carboxylate ester was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument. The 1H NMR spectrum was characterized by the following chemical shifts (delta, ppm): 0.87 -1.09 (t, 3H); 1.42 - 1.70 (m, 2H); 1.75 - 1.88 (q, 2H); 4.26 -4.64 (t, 2H); 7.29 -7.45 (m, 2H); 7.46 -7.58 (m, 1H); 7.60 - 7.68 (dd, 1H); 7.75 - 7.82 (dd, 1H); 7.90 - 8.00 (dd, 1H); and 8.25 - 8.35 (dd, 1H).
  • 82
  • N-(biphenyl-4-methyl)-3-amino-benzoic acid amide [ No CAS ]
  • [ 6223-83-2 ]
  • N-(biphenyl-4-methyl)-3-(9-oxofluorene-4-carbonylamino)-benzoic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N-methyl-acetamide; EXAMPLE 122 N-(biphenyl-4-methyl)-3-(9-oxofluorene-4-carbonylamino)-benzoic acid amide Prepared analogously to Example 34 from 3-amino-N-(biphenyl-4-methyl)-benzoic acid amide, <strong>[6223-83-2]9-oxofluorene-4-carboxylic acid</strong>, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield:33% of theory Rf value:0.37 (silica gel; dichloromethane/ethanol=95:5)
  • 83
  • aluminum hydroxide [ No CAS ]
  • [ 104-51-8 ]
  • [ 6223-83-2 ]
  • [ 107-06-2 ]
  • [ 130099-56-8 ]
YieldReaction ConditionsOperation in experiment
36.4% With potassium hydroxide; thionyl chloride;aluminium trichloride; In dichloromethane; nitrogen; ethyl acetate; EXAMPLE 1 25.0 g (111 mmol) of <strong>[6223-83-2]9-fluorenone-4-carboxylic acid</strong> and 300 mlambda of thionyl chloride were placed in a 500 mlambda three-necked flask and refluxed in a stream of nitrogen for 5 hours. Then the thionyl chloride was distilled away under reduced pressure, and 100 mlambda of 1,2-dichloroethane was added to the resulting residue and distilled away under reduced presure to remove the remaining thionyl chloride. To the acid chloride thus formed was added 200 mlambda of methylene chloride. After cooling to -20 C. in a cooling bath, 20.0 g (150 mmol) of aluminum chloride was added and the resulting mixture was stirred in a stream of nitrogen for 15 hours. Then, a solution comprising 15.9 g (118 mmol) of n-butylbenzene and 50 mlambda of methylene chloride was dropped over 30 minutes. After the completion of dropping, stirring was continued for 3 hours, and after removing from the cooling bath, stirring was continued at room temperature for 20 hours. Moreover, 7.5 g of (56.3 mmol) of aluminum chloride was added, stirred for 2.5 hours and then poured onto 150 g of ice. A 20% potassium hydroxide solution was added until aluminum hydroxide was dissolved, and an organic layer was separated. An aqueous layer was extracted with methylene chloride, and the organic layers obtained were combined and the solvent was distilled away under reduced pressure. To the resulting residue was added 200 mlambda of 5% potassium hydroxide, and the resulting mixture was heated at 80 C. to decompose the remaining acid chloride. Then the product was extracted with methylene chloride. After purification on a silica gel short column (elution with methylene chloride) and distillation of the solvent, the product was recrystallized from hexane and then from ethyl acetate to obtain 13.8 g of 4-(4'-n-butyl-phenylcarbonyl)fluorene-9-one as a yellow powder (yield 36.4 %). M.p., 93-95 C. Infrared absorption spectrum: 1726, 1720 cm31 1 (C=O)(KBr)
  • 84
  • [ 6223-83-2 ]
  • [ 7071-86-5 ]
YieldReaction ConditionsOperation in experiment
12.4 g (88.5%) In tetrahydrofuran; 9-Hydroxyfluorene-4-methanol A solution of <strong>[6223-83-2]9-fluorenone-4-carboxylic acid</strong> (14.8 g, 66 mmol) in 250 mL of THF, at 0 C was charged with a solution of 1M borane-THF complex in THF (150 mL, 150 mmol). The temperature was slowly elevated to room temperature. After 1.5 hr at room temperature the reaction was quenched with water. The reaction mixture was diluted with EtOAc. The organic layer was washed with water (*3), dried over magnesium sulfate and evaporated. Recrystallization from ether with traces of EtOAc afforded 12.4 g (88.5%) of the diol.
  • 85
  • [ 6223-83-2 ]
  • 4-[(9H-fluorenone-9-one-4-yl)carbonyloxymethyl]Peroxybenzoic Acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In tetrachloromethane; water; acetonitrile; Preparation of 4-[(9H-fluorenone-9-one-4-yl)carbonyloxymethyl]Peroxybenzoic Acid, tert-Butyl Ester (Formula IV) 4-Carboxyfluorenone (896 mg, 4 mmoles) was treated was a suspension in 50 ml of water with an equivalent amount of KOH solution (224 mg KOH; approximately 4 mmoles; pH of the solution close to 7.0). Filtration removed the small amount of undissolved solid and the obtained filtrate was evaporated to dryness. The so obtained potassium salt of the acid was thoroughly dried in an Abderhalen drying apparatus. A suspension was made of the potassium salt in 10 ml of dry acetonitrile and 0.65 of the 4-bromomethyl Formula I perester (2 mmoles) and 60 mg of 18-crown-6(0.23 mmoles) added. The mixture was stirred for 16 hr. in the dark while the progress of the reaction followed by TLC. Evaporation and chromatography, on silica gel with 1:1 carbon tetrachloride/chloroform as the eluding solvent gave 0.85 g of the perester as a yellow oil. Recrystallization from cyclohexane gave yellow crystals, mp. 102-104. IR (KBr): 1750 cm-1 (nuC=O adjacent to perester); 1725 cm-1 (nuC=O ester); 1710 cm-1 (nuC=O ketone). Analysis: Calc; C=72.56, H=5.11. Found: C=72.65; H=5.15. NMR: (CDCl3) delta=1.4, s 9H, methyl; delta=5.4, s, 2H, methylene; delta=7.49-8.03, m, 11H aromatic protons,
  • 86
  • [ 110-89-4 ]
  • [ 6223-83-2 ]
  • [ 109-77-3 ]
  • [ 36232-49-2 ]
YieldReaction ConditionsOperation in experiment
In methanol; (a) Preparation of precursor (4-carboxy-9-florenylidene)malononitrile: A mixture of 93.1 grams (0.415 mole) of fluorenone-4-carboxylic acid and 750 milliliters of absolute methanol was magnetically stirred and heated to reflux temperature in a 2,000 milliliter round-bottomed flask fitted with a reflux condenser. Subsequently, there was added to the flask 82.3 grams (1.25 mole) of malononitrile and 20 drops of piperidine. This mixture was then heated under reflux for 48 hours. The solid product (4-carboxy-9-fluorenylidene)malononitrile, was collected by suction filtration, and purified by stirring in 500 milliliters of boiling methanol for 15 minutes, followed by filtration and washing successively with 200 milliliters of methanol. The product was dried under vacuum at 65 C. for 12 hours and weighed 90.1 grams.
  • 87
  • [ 863305-32-2 ]
  • [ 6223-83-2 ]
  • [ 93376-18-2 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; In water; Preparation of (4-n-Butoxycarbonyl-9-fluorenylidene)malononitrile A 460 g quantity of concentrated sulfuric acid (4.7 moles, analytical grade, from Sigma-Aldrich, Milwaukee, WI) and 100 g of diphenic acid (0.41 mole, from Acros Fisher Scientific Company Inc., Hanover Park, IL) were added to a 1-liter 3-neck round bottom flask, equipped with a thermometer, mechanical stirrer and reflux condenser. Using a heating mantle, the flask was heated to 135-145 C for 12 minutes. After cooling to room temperature, the solution was added to a 4-liter Erlenmeyer flask containing 3 liter of water. The mixture was stirred mechanically and brought to a gentle boil for one hour. The yellow solid that formed was filtered out hot, washed with hot water until the pH of the washing water was neutral, and dried overnight in the fume-hood. The yellow solid was fluorenone-4-carboxylic acid (75 g, 80% yield). The product had a melting point of 223-224 C. The 1H NMR spectrum (300 MHz) of the product in CDCl3 was characterized by the following chemical shifts (delta, ppm): 7.39-7.50 (m, 2H); 7.79 - 7.70 (q, 2H); 7.74 - 7.85 (d, 1H); 7.88 -8.00 (d, 1H); and 8.18 - 8.30 (d, 1H), where d is doublet, t is triplet, m is multiplet; dd is double doublet, q is quintet.
  • 88
  • [ 6223-83-2 ]
  • [ 93519-65-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; sodium hydrogencarbonate; In water; toluene; A 70 g (0.312 mole) quantity of fluorenone-4-carboxylic acid, 480 g (6.5 mole) of n-butanol (commercially obtained from Fisher Scientific Company Inc., Hanover Park, Ill.), 1000 ml of toluene and 4 ml of concentrated sulfuric acid were added to a 2-liter round bottom flask equipped with a mechanical stirrer and a reflux condenser with a Dean Stark apparatus. With aggressive agitation and refluxing, the solution was refluxed for 5 hours, during which about 6 g of water were collected in the Dean Stark apparatus. The flask was cooled to room temperature. The solvents were evaporated, and the residue was added, with agitation, to 4 liters of a 3% sodium bicarbonate aqueous solution. The solid was filtered off, washed with water until the pH of the wash-water was neutral, and dried in the hood overnight. The product was n-butyl fluorenone-4carboxylate ester. The yield was 70 g (80%). A 1H-NMR spectrum of n-butyl fluorenone-4-carboxylate ester was obtained in CDCl3 with a 300 MHz NMR from Bruker Instrument.
  • 89
  • [ 110-63-4 ]
  • [ 6223-83-2 ]
  • [ 1105063-54-4 ]
  • 90
  • [ 6223-83-2 ]
  • [ 107-21-1 ]
  • [ 190431-84-6 ]
  • 91
  • [ 6223-83-2 ]
  • [ 504-63-2 ]
  • [ 401599-54-0 ]
  • 92
  • [ 6223-83-2 ]
  • [ 883-33-0 ]
YieldReaction ConditionsOperation in experiment
With [bis(acetoxy)iodo]benzene; iodine; In tetrachloromethane; at 78℃; for 20.0h;Photochemical reactor; Irradiation; Example 2 Synthesis of [4-(benzofuran-2-yl)-9H-fluoren-9(R,S)-yl)]-amide of 1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid Stage 1: Introduce successively 5 g of <strong>[6223-83-2]9-fluorenone-4-carboxylic acid</strong>, 22 g of iodobenzene diacetate, 17 g of doubly sublimed iodine and 450 mL of carbon tetrachloride in a photochemical reactor containing a 125 W lamp. After heating for 20 hours at 78 C. under radiation, add 300 mL of a 10% aqueous solution of sodium thiosulphate and stir for 15 minutes. Remove the precipitate (unreacted starting product) and purify the organic phase of the filtrate by flash chromatography on silica gel (20-40 mum), eluding with a mixture of cyclohexane and ethyl acetate (90-10 by volume). We thus obtain 1.59 g of 4-iodo-fluoren-9-one in the form of a yellow solid with the following characteristics: Mass spectrum (E/I): m/z=306 (M+) 1H NMR spectrum (400 MHz, delta in ppm, DMSO-d6): 7.14 (t, J=8.0 Hz, 1H); 7.48 (d broad, J=7.5 Hz, 1H); 7.66 (dd, J=1.0 and 7.5 Hz, 1H); 7.69 (d broad, J=8.0 Hz, 1H); 7.74 (dt, J=1.0 and 7.5 Hz, 1H); 8.05 (dd, J=1.0 and 7.5 Hz, 1H); 8.59 (d broad, J=8.0 Hz, 1H).
  • 93
  • [ 3182-95-4 ]
  • [ 6223-83-2 ]
  • [ 1245618-44-3 ]
  • [ 1245618-55-6 ]
  • 94
  • (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride [ No CAS ]
  • [ 6223-83-2 ]
  • N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethyl)-9-oxo-9H-fluorene-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% To a solution of <strong>[6223-83-2]9-oxo-9H-fluorene-4-carboxylic acid</strong> (144 mg, 0.64 mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.11 ml, 1.72 mmol) and N,N-dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solution was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (5 ml) were added (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (150 mg, 0.43 mmol) and saturated aqueous sodium hydrogen carbonate (5 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml), and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1) and recrystallized from ethyl acetate-hexane to give the title c! ompound (154 mg, 69%). mp 231-232C IR nu maxKBr cm-1: 1725, 1638, 1607. Anal. Calcd for C30H21F4NO3: C, 69.36; H, 4.07; N, 2.70 Found: C, 69.13; H, 4.22; N, 2.53.1H-NMR (CD3OD) delta: 2.78-2.96 (1H, m), 3.49 (1H, d, J = 13.2 Hz), 4.70-4.80 (2H, m), 6.72 (1H, d, J = 7.4 Hz), 6.89 (1H, d, J = 7.8 Hz), 7.04-7.32 (5H, m), 7.46-7.66 (8H, m).
  • 95
  • [ 6223-83-2 ]
  • [ 20989-17-7 ]
  • [ 1424273-26-6 ]
  • [ 1424273-27-7 ]
YieldReaction ConditionsOperation in experiment
53%; 24% With carbon tetrabromide; triethylamine; triphenylphosphine; In toluene; at 90℃; for 14.0h;Inert atmosphere; General procedure: A 200 mL three-necked flask equipped with a condenser was charged with Ph3P (2.20 g, 8.4 mmol), Et3N (0.85 g, 8.4 mmol), CBr4 (16.8 g, 8.4 mmol), substrate 1 (3.3 mmol), and aromatic acid 2 (2.8 mmol) in toluene (15.0 mL) under a nitrogen atmosphere. The solution was stirred for approximately 20 min at room temperature, then the mixture was heated at 90 C with stirring for 6-14 h. The solvent was evaporated under reduced pressure, and the residue was diluted with petroleum ether (60-90 C) and filtered. The residual solid Ph3PO and Et3N·HBr was washed with petroleum ether three times. The filtrate was concentrated, and the residue was separated by column chromatography (ethyl acetate/petroleum ether, 1:8) to afford product 3 and 3?. If the mixture was processed after stirring for 0.5 h at 90 C, intermediate 6 was obtained by column chromatography (ethyl acetate/petroleum ether=1:8).
  • 96
  • [ 1435684-52-8 ]
  • [ 6223-83-2 ]
  • [ 1435685-72-5 ]
YieldReaction ConditionsOperation in experiment
81% With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 15.0h; General procedure: A mixture of compound 10 (135 mg, 0.49 mmol) and 4-(thiophen-3-yl)benzoic acid (99.4 mg, 0.49 mmol) in dichloromethane (10 mL) was stirred at 0 C (ice-water bath). Dicyclohexylcarbodiimide(DCC) (121 mg, 0.59 mmol) and hydroxybenzotriazole(HOBt) (80 mg, 0.59 mmol) were added to the above solution.The ice bath was removed, and the reaction mixture was stirred at ambient temperature for 15 h. Dichloromethane (20 mL) was added into the reaction mixture, and the solution was washed with saturated aqueous NaHCO3 solution (3*10 mL). The organic layer was dried over Na2SO4, concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography using dichloromethane-methanol (20:1) as the mobile phase to give 11a as a white solid (194 mg, 86%). TLC Rf 0.20 (dichloromethane-methanol 20:1); mp 125.5-126.6 C. 1H NMR(300 MHz, CDCl3) delta 7.75 (d, J = 8.7 Hz, 2H), 7.54 (d, J = 8.7 Hz, 2H),7.43 (s, 1H), 7.33 (s, 2H), 7.19 (s, 1H), 6.81-6.94 (m, 4H), 3.85 (s,3H), 3.44 (q, J = 5.1 Hz, 2H), 3.25-3.20 (m, 4H), 2.83-2.76 (m,4H), 2.57 (t, J = 5.2 Hz, 2H), 1.93 (t, J = 4.2 Hz, 2H), 1.61-1.69 (m,4H). 13C NMR (CDCl3, 300 MHz): 167.4, 151.4, 142.1, 141.2,138.8, 133.4, 127.5, 126.6, 126.3, 126.1, 121.3, 121.0, 120.7,117.9, 111.6, 57.1, 56.1, 55.3, 54.3, 52.5, 51.8, 39.4, 27.7, 27.3,25.5. HRMS (ESI) Calcd for C27H33N3O2S (M+H)+: 464.2372. Found:464.2379. Anal. (C27H33N3O2S 1.5H2C2O4) C, H, N.
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