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[ CAS No. 54177-02-5 ] {[proInfo.proName]}

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Chemical Structure| 54177-02-5
Chemical Structure| 54177-02-5
Structure of 54177-02-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54177-02-5 ]

CAS No. :54177-02-5 MDL No. :MFCD03424780
Formula : C11H12O4 Boiling Point : -
Linear Structure Formula :- InChI Key :OEIWRCBBMGTEMA-UHFFFAOYSA-N
M.W : 208.21 Pubchem ID :2759697
Synonyms :

Calculated chemistry of [ 54177-02-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.03
TPSA : 52.6 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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 1.44
Log Po/w (MLOGP) : 1.03
Log Po/w (SILICOS-IT) : 1.99
Consensus Log Po/w : 1.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.26
Solubility : 1.15 mg/ml ; 0.00554 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.567 mg/ml ; 0.00272 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.228 mg/ml ; 0.00109 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 54177-02-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54177-02-5 ]

* 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 [ 54177-02-5 ]

[ 54177-02-5 ] Synthesis Path-Downstream   1~56

  • 1
  • [ 67-56-1 ]
  • [ 54177-02-5 ]
  • [ 127-09-3 ]
  • [ 100-34-5 ]
  • 3-(2-methoxy-phenyl)-3-oxo-2-phenylhydrazono-propionic acid methyl ester [ No CAS ]
  • 3
  • [ 54177-02-5 ]
  • [ 100-34-5 ]
  • 3-(2-methoxy-phenyl)-3-oxo-2-phenylhydrazono-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With methanol; sodium acetate
  • 4
  • [ 54177-02-5 ]
  • 2-hydroxyimino-3-(2-methoxy-phenyl)-3-oxo-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; sodium nitrite
  • 5
  • [ 54177-02-5 ]
  • 3-(2-methoxy-benzoyl)-6-(2-methoxy-phenyl)-pyran-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
bei der Destillation unter vermindertem Druck;
  • 6
  • [ 54177-02-5 ]
  • [ 100-63-0 ]
  • [ 939898-79-0 ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid
  • 7
  • [ 79-37-8 ]
  • [ 54177-02-5 ]
  • [ 134567-91-2 ]
YieldReaction ConditionsOperation in experiment
78% With magnesium chloride In diethyl ether at 20℃; for 2h;
YieldReaction ConditionsOperation in experiment
91.7% 23 Methyl-3-(methoxyphenyl)-3-oxopropionate Methyl-3-(methoxyphenyl)-3-oxopropionate Bis-(trimethylsilyl)amine (158.2 mL, 0.750 mol) was dissolved in 150 mL of THF and cooled to -78° C. with the aid of a dry ice/acetone bath. N-butyl lithium (2.5 M in hexane, 300 mL, 0.750 mol) was introduced via cannula into the system and stirred at that temperature for 20 min. 4-methoxy acetophenone (51.20 g, 0.340 mol) was added via a solid addition funnel and stirred at -78° C. for 3 h. Dimethylcarbonate (87.0 mL, 1.02 mol) was added via cannula and the system allowed to stir overnight with warming to room temperature. The solution was acidified with 10% HCl, diluted with 1 liter of EtOAc and washed three times with 400 mL of 10% HCl. The organics were dried over MgSO4, filtered through a silica gel plug and the volatiles removed in vacuum. The title compound was obtained as a viscous brown oil (65.09 g, 91.7%) MS (NH3 -DCI) 347.9 (M+H)+.
o-Methoxyacetophenon, NaOMe / Dimethylcarbonat;
YieldReaction ConditionsOperation in experiment
bei der Destillation;
  • 15
  • [ 54177-02-5 ]
  • 3-(2-methoxy-phenyl)-2-(4-nitro-phenylhydrazono)-3-oxo-propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid
  • 16
  • [ 54177-02-5 ]
  • [ 108-24-7 ]
  • [ 434957-34-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2-methoxybenzoylacetate With ammonium acetate In methanol Stage #2: acetic anhydride With pyridine In tetrahydrofuran Heating;
  • 17
  • [ 54177-02-5 ]
  • [ 62-53-3 ]
  • 3-(2-methoxyphenyl)-3-phenylaminoacrylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With toluene-4-sulfonic acid In ethanol Heating;
  • 18
  • [ 54177-02-5 ]
  • (2-methoxy-phenyl)-oxo-acetaldehyde oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2-methoxybenzoylacetate With sodium hydroxide In water for 12h; Stage #2: With perchloric acid; sodium nitrite In water at 20℃; for 14h;
  • 19
  • [ 54177-02-5 ]
  • [(Z)-Hydroxyimino]-(2-methoxy-phenyl)-acetaldehyde oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 2-methoxybenzoylacetate With sodium hydroxide In water for 12h; Stage #2: With perchloric acid; sodium nitrite In water at 20℃; for 14h; Stage #3: With sodium hydroxide; hydroxylamine hydrochloride In water Heating;
  • 20
  • [ 54177-02-5 ]
  • [ 31596-58-4 ]
YieldReaction ConditionsOperation in experiment
47% Multistep reaction;
  • 21
  • [ 54177-02-5 ]
  • [ 654061-87-7 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate In methanol at 20℃; for 72h;
  • 22
  • [ 54177-02-5 ]
  • 3-(2-methoxyphenyl)-3-phenylaminopropionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 67 percent / TsOH*H2O / ethanol / Heating 2: H2; [Rh(S,S,R,R)TangPhos(nbd)]SbF6 / 2,2,2-trifluoro-ethanol / 24 h / 80 °C / 4560 Torr
  • 23
  • [ 54177-02-5 ]
  • 3-(2-methoxyphenyl)-3-phenylaminopropionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 67 percent / TsOH*H2O / ethanol / Heating 2: H2; [Rh(S,S,R,R)TangPhos(nbd)]SbF6 / 2,2,2-trifluoro-ethanol / 24 h / 80 °C / 4560 Torr
  • 24
  • [ 54177-02-5 ]
  • (S)-methyl 3-acetamido-3-(2-methoxyphenyl)-propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NH4OAc / methanol 1.2: pyridine / tetrahydrofuran / Heating 2.1: H2 / [Rh((S,S,S)-binapine)(3,5-norbornadiene)]SbF6 / tetrahydrofuran / 24 h / 20 °C / 1034.3 Torr
  • 25
  • [ 54177-02-5 ]
  • [ 434957-34-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NH4OAc / methanol / 72 h / 20 °C 2: pyridine / tetrahydrofuran / 72 h / Heating
  • 26
  • [ 54177-02-5 ]
  • [ 96-34-4 ]
  • dimethyl 2-methoxybenzoylsuccinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.7 g (59.0%) With potassium carbonate In methanol; 1,2-dimethoxyethane; acetone 1 Dimethyl 2-methoxybenzoylsuccinate Dimethyl 2-methoxybenzoylsuccinate 91.16 g (440 mmol) of methyl 2-methoxybenzoylacetate, 57.5 g (530 mmol) of methyl chloroacetate, 280 ml of acetone, 190 ml of dimethoxyethane and 70.0 g (510 mmol) of potassium carbonate are boiled under reflux for 22 hours. After cooling to room temperature, the mixture is filtered with suction and the residue is washed with n-hexane. The combined filtrates are concentrated on a rotary evaporator and 70 ml of methanol are added to the oil which remains. After a short time, the dimethyl 2-methoxybenzoylsuccinate crystallises out. Yield 73.7 g (59.0%) of colorless crystals, melting point 75°-76° C. (methanol), Rf (silica gel/ethyl acetate)=0.83. C14 H16 O6 (280.2) Calc.: C, 59.99; H 5.75. Found: C 60.28; H 5.75.
  • 27
  • [ 579-74-8 ]
  • [ 54177-02-5 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In carbonic acid dimethyl ester 5 EXAMPLE 5 EXAMPLE 5 The procedure is as described in Example 1, except that 95 g of sodium methylate in 800 ml dimethylcarbonate are used and 250 g of o-methoxyacetophenone are added dropwise over a period of 5 hours at 90°C, the alcohol formed being simultaneously distilled off at normal pressure. Working up in accordance with Example 1 gives 100 g of unreacted starting material and 162 g of o-methoxybenzoylacetic acid methyl ester boiling at 130° to 133°C/0.07 torr (= 78% of the theoretical amount based on the reacted o-methoxyacetophenone).
  • 28
  • [ 54177-02-5 ]
  • [ 106-96-7 ]
  • [ 1242162-68-0 ]
YieldReaction ConditionsOperation in experiment
57% With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 20℃; for 24h; Inert atmosphere;
  • 29
  • [ 54177-02-5 ]
  • [ 75-03-6 ]
  • [ 1159586-51-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In tetrahydrofuran at 80℃; for 13h; 101 To a suspension of methyl 3-(2-methoxy phenyl)-3-oxopropanoate (5.08 g) and potassium carbonate (5.0 g) in tetrahydrofuran (50 ml) was added ethyl iodide (2.5 ml), followed by stirring at 80°C for 13 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate, and the organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate) to obtain the compound of Preparative Example 101 (4.51 g) as a pale yellow oily substance.
  • 30
  • [ 579-74-8 ]
  • [ 616-38-6 ]
  • [ 54177-02-5 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride In toluene; mineral oil for 0.5h; Reflux; General Procedure A: Synthesis of the phenyliodonium ylides of β-ketoesters General procedure: In a dry two neck flask equipped with a reflux condenser and rubber septum and a stir bar, NaH (60% wt in mineral oil, 4.0 g, 100 mmol) was suspended in toluene (8 mL) and dimethylcarbonate (9.1 g, 100 mmol, 2.5 eq) was added. The mixture was heated to reflux and acetophenone (4.8 g, 40 mmol, 1.0 eq) in toluene (20 mL) was added dropwise. The reaction mixture was stir for 0.5 h when hydrogen evolution had ceased.The suspension was cooled to 0 °C, diluted with EtOAc (150 mL) and carefully quenched with MeOH (10 mL), followed by H2O, and then acidified to pH < 5 using 1N HCl. The organic layer is separated and then washed with H2O (200 mL) then brine (100 mL), and dried over MgSO4, and concentrated in vacuo. The resulting biphasic liquid was partitioned between MeCN (20 mL) and hexanes (10 mL) and then washed with hexanes (25 mL x 2) and concentrated in vacuo to give the β-ketoesters. Dicarbonyl compound (6mmol) was dissolved in MeOH (6 mL) and then cooled in a brine-ice bath. Then, 30% KOH in MeOH (6 mL) solution was added dropwise an the mixture was allowed to stir for 2 minutes after which a solution of iodobenzene diacetate (6 mmol) was added dropwise and the resulting mixture was allowed to stir for 1 hr and then poured onto icewater (100 mL). The suspension is then extracted with CH2Cl2 (50 mL x 3). The combined extracts were dried over MgSO4, filtered through Buchner funnel, then concentrated in vacuo to approximately one third of the original volume. The ylide was slowly precipitated using Et2O and/or hexanes, and cooled to 0 °C and isolated by filtration.
87% With sodium hydride at 20 - 50℃; for 3.5h; 14 Methyl 3-(2-methoxyphenyl)-3-oxopropanoate Methyl 3-(2-methoxyphenyl)-3-oxopropanoate Sodium hydride (1.9 g, 55.42 mmol, 3.00 equiv, 70%) was added portionwise to a solution of 1-(2-methoxyphenyl)ethanone (4 g, 26.67 mmol, 1.00 equiv) in dimethyl carbonate (40 mL) at 0° C. The reaction was stirred for 1 h at room temperature, then for an additional 2.5 h at 50° C. Then the reaction was quenched by the addition of 50 mL of ice/water. The pH of the aqueous solution was adjusted to 2 with HCl (1N). The resulting solution was extracted with 2*20 mL of ethyl acetate. The organic layers were combined and concentrated in vacuo. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:2). This resulted in 4.8 g (87%) of methyl 3-(2-methoxyphenyl)-3-oxopropanoate as yellow green oil.
21% With sodium hydride In tetrahydrofuran; toluene at 70℃; for 4h;
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran for 0.5h; Reflux; Stage #2: 2-Methoxyacetophenone In tetrahydrofuran Reflux;
With sodium hydride In toluene; mineral oil for 5h; Reflux; 1.2.2 General procedure B: preparation of β-ketoesters 1b. General procedure: To a solution of ketone (20 mmol) in toluene (80 mL) was added dimethyl carbonate (60 mmol) and NaH (40 mmol, 60%). The reaction mixture was refluxed for 5 h until TLC indicated the total consumption of the ketone. After cooling, the reaction mixture was poured into ice-water (100 mL), acidified with 3 M HCl to pH 2-3 and extracted with EtOAc (100 mL x3). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (petroleum ether /EtOAc = 10/1) to afford the desired compound.
With sodium hydride In tetrahydrofuran at 0℃; Reflux;

  • 31
  • [ 54177-02-5 ]
  • [ 1202873-86-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: methanol / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h 2.2: 3 h / 80 °C 3.1: tetrahydrofuran / 1 h / Reflux
  • 32
  • [ 54177-02-5 ]
  • [ 1202873-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol / Reflux 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h 2.2: 3 h / 80 °C
  • 34
  • [ 54177-02-5 ]
  • [ 125889-79-4 ]
  • 5-(2-methoxyphenyl)spiro[1,3-dihydro-1,4-diazepine-2,3'-quinuclidine]-7-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 2-methyl-propan-1-ol at 100℃; 5-Phenylspiro[1,3-dihydro-1,4-diazepine-2,3'-quinuclidine]-7-ol (2a) General procedure: This procedure illustrates the general method for preparation of 2a-g. 3-Amino-3-(aminomethyl)quinuclidine (1) (75 mg, 0.5 mmol) and ethyl benzoylacetate (100 mg, 0.5 mmol) were dissolved in i-butanol (3 ml). The reaction mixture was heated at 100 °C overnight, cooled to ambient temperature and concentrated. The residue was purified by preparative HPLC to yield 2a trifluoroacetate (105 mg, 53%).
  • 35
  • [ 54177-02-5 ]
  • [ 24031-70-7 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydrogencarbonate; ammonium chloride In ethanol for 6h; Reflux; A solution of 13.0 g (58.5 mmol) of methyl 2-methoxybenzoylacetate, 10.0 g (144 mmol) of hydroxylammonium chloride and 10.0 g (119 mmol) of sodium bicarbonate in 100 ml of ethanol was heated at reflux for 6 h. The solvent was then distilled off, water was added, the mixture was acidified with diluted hydrochloric acid and the resulting precipitated solid was filtered off with suction, washed with ethanol and dried under reduced pressure. This gave, in a purity of 95% (HPLC), 11.4 g (59.6 mmol, 96% of theory) of 3-(2-methoxyphenyl)isoxazol-5(4H)-one having a log P (HCOOH)=1.67.
  • 36
  • [ 54177-02-5 ]
  • [ 1352952-13-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; ammonium chloride / ethanol / 6 h / Reflux 2: morpholine / toluene / 15 h / Reflux
  • 37
  • [ 54177-02-5 ]
  • [ 593-56-6 ]
  • cis-methyl 3-(methoxyimino)-3-(2-methoxyphenyl)propanoate [ No CAS ]
  • [ 1372793-74-2 ]
YieldReaction ConditionsOperation in experiment
With pyridine at 20℃; for 3h; optical yield given as %de;
  • 38
  • [ 54177-02-5 ]
  • [ 501-65-5 ]
  • C25H20O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper diacetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;
  • 39
  • [ 3240-34-4 ]
  • [ 54177-02-5 ]
  • C17H15IO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With potassium hydroxide In methanol for 1h; Cooling with ice; General Procedure A: Synthesis of the phenyliodonium ylides of β-ketoesters General procedure: In a dry two neck flask equipped with a reflux condenser and rubber septum and a stir bar, NaH (60% wt in mineral oil, 4.0 g, 100 mmol) was suspended in toluene (8 mL) and dimethylcarbonate (9.1 g, 100 mmol, 2.5 eq) was added. The mixture was heated to reflux and acetophenone (4.8 g, 40 mmol, 1.0 eq) in toluene (20 mL) was added dropwise. The reaction mixture was stir for 0.5 h when hydrogen evolution had ceased.The suspension was cooled to 0 °C, diluted with EtOAc (150 mL) and carefully quenched with MeOH (10 mL), followed by H2O, and then acidified to pH < 5 using 1N HCl. The organic layer is separated and then washed with H2O (200 mL) then brine (100 mL), and dried over MgSO4, and concentrated in vacuo. The resulting biphasic liquid was partitioned between MeCN (20 mL) and hexanes (10 mL) and then washed with hexanes (25 mL x 2) and concentrated in vacuo to give the β-ketoesters. Dicarbonyl compound (6mmol) was dissolved in MeOH (6 mL) and then cooled in a brine-ice bath. Then, 30% KOH in MeOH (6 mL) solution was added dropwise an the mixture was allowed to stir for 2 minutes after which a solution of iodobenzene diacetate (6 mmol) was added dropwise and the resulting mixture was allowed to stir for 1 hr and then poured onto icewater (100 mL). The suspension is then extracted with CH2Cl2 (50 mL x 3). The combined extracts were dried over MgSO4, filtered through Buchner funnel, then concentrated in vacuo to approximately one third of the original volume. The ylide was slowly precipitated using Et2O and/or hexanes, and cooled to 0 °C and isolated by filtration.
  • 40
  • [ 54177-02-5 ]
  • methyl (2-anisoyl)dichloroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 1 h / Cooling with ice 2: (Dichloroiodo)benzene / acetonitrile / 0.08 h / 0 °C / Sonication; Inert atmosphere
  • 41
  • [ 54177-02-5 ]
  • methyl 2-chloro-3-(2-methoxyphenyl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: methyl 2-methoxybenzoylacetate With chloro-trimethyl-silane In acetonitrile at 20℃; for 0.166667h; Stage #2: With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 2h; Modified Chlorination of 1,3-Dicarbonyl Compounds 1bc, 1be, 1bi, 1bj and 1ce-1ci; General Procedure General procedure: To a solution of a 1,3-dicarbonyl compound (0.26 mmol, 1 equiv) in MeCN (3 mL) was added TMSCl (0.26 mmol, 1 equiv). After the reaction mixture was stirred at r.t. for 10 min, PhI(OAc)2 (0.26 mmol, 1equiv) was added. The mixture was stirred at r.t. and monitored byTLC. After the starting material was no longer detected (TLC, 5-60min), the reaction mixture was poured into ice-water (10 mL). The mixture was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to afford the desired monochlorinated compound.
  • 42
  • [ 54177-02-5 ]
  • methyl 2,2-dichloro-3-(5-chloro-2-methoxyphenyl)-3-oxopropa-noate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: methyl 2-methoxybenzoylacetate With chloro-trimethyl-silane In acetonitrile at 20℃; for 0.166667h; Stage #2: With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.5h; Compounds 4a, 4b and 4c; General Chlorination Procedure General procedure: To a solution of 1,3-dicarbonyl compound 1a, 1b or 1c (0.26 mmol, 1equiv) in MeCN (3 mL) was added TMSCl (1.04 mmol, 4 equiv). After the reaction mixture was stirred at r.t. for 10 min, PhI(OAc)2 (0.26mmol, 1 equiv) was added. The mixture was stirred at r.t. and monitored by TLC. After the starting material was no longer detected (TLC), the reaction mixture was poured into ice-water (10 mL). The mixture was extracted with CH2Cl2 and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography to afford compound 4a, 4b or 4c.
  • 43
  • [ 54177-02-5 ]
  • ethyl 3-(cyclopropylamino)-2-(2-methoxybenzoyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 12 h / 65 °C 2: methanol / 8 h / 20 °C
  • 44
  • [ 54177-02-5 ]
  • methyl 2-(2-methoxybenzoyl)-3-(phenylamino)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 12 h / 65 °C 2: toluene / 20 - 100 °C
  • 45
  • [ 54177-02-5 ]
  • methyl 1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene / 12 h / 65 °C 2: methanol / 8 h / 20 °C 3: N,O-bis-(trimethylsilyl)-acetamide / N,N-dimethyl-formamide / 100 °C / Inert atmosphere
  • 46
  • [ 54177-02-5 ]
  • 4-oxo-1-phenyl-1,4-dihydroquinoline-3-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: toluene / 12 h / 65 °C 2: toluene / 20 - 100 °C 3: N,O-bis-(trimethylsilyl)-acetamide / N,N-dimethyl-formamide / 100 °C / Inert atmosphere
  • 47
  • [ 54177-02-5 ]
  • [ 4637-24-5 ]
  • methyl 3-(dimethylamino)-2-(2-methoxybenzoyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In toluene at 65℃; for 12h;
  • 48
  • [ 54177-02-5 ]
  • [ 95-54-5 ]
  • 4-(2-methoxyphenyl)-1,5-benzodiazepin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In para-xylene for 2h; Reflux;
  • 49
  • [ 54177-02-5 ]
  • Trifluoromethyl diethylaminosulfur difluoride [ No CAS ]
  • C12H11F3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In dichloromethane; acetonitrile at 40℃; Inert atmosphere;
  • 50
  • [ 54177-02-5 ]
  • Perfluorophenyl Diethylaminosulfur Difluoride [ No CAS ]
  • methyl 5,6,7,8-tetrafluoro-2-(2-methoxyphenyl)benzo[b][1,4]oxathiine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: methyl 2-methoxybenzoylacetate In di-isopropyl ether at 20℃; for 0.166667h; Inert atmosphere; Stage #2: Perfluorophenyl Diethylaminosulfur Difluoride In dichloromethane at 70℃; for 12h; Inert atmosphere;
  • 51
  • [ 118-93-4 ]
  • [ 54177-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux 2: sodium hydride / tetrahydrofuran / 0 °C / Reflux
  • 52
  • [ 54177-02-5 ]
  • 5'-bromo-1'-methyl-3H-spiro[benzofuran-2,3'-indoline]-2',3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap / toluene / 15 h / Reflux 2: bis-[(trifluoroacetoxy)iodo]benzene / 1,2-dichloro-ethane / 20 °C
  • 53
  • [ 6911-87-1 ]
  • [ 54177-02-5 ]
  • N-(4-bromophenyl)-3-(2-methoxyphenyl)-N-methyl-3-oxopropanamide [ No CAS ]
  • C17H16BrNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In toluene for 15h; Reflux;
  • 54
  • [ 54177-02-5 ]
  • methyl 2-diazo-3-(2-methoxyphenyl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With sodium azide; 3-Carboxybenzenesulfonyl chloride; potassium carbonate In water; acetonitrile at 20℃; for 2h;
  • 55
  • [ 54177-02-5 ]
  • [ 100-46-9 ]
  • N-benzyl-3-(2-methoxyphenyl)-3-oxopropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: methyl 2-methoxybenzoylacetate With dmap In ethanol at 80℃; for 1h; Inert atmosphere; Stage #2: benzylamine In ethanol at 80℃; for 24h; Inert atmosphere;
  • 56
  • [ 54177-02-5 ]
  • (S)-N-benzyl-3-hydroxy-3-(2-methoxyphenyl)propanamide [ No CAS ]
  • (R)-N-benzyl-3-hydroxy-3-(2-methoxyphenyl)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dmap / ethanol / 1 h / 80 °C / Inert atmosphere 1.2: 24 h / 80 °C / Inert atmosphere 2.1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; <i>tert</i>-butyl alcohol; C23H29BrNO6V / tetrahydrofuran / -20 °C / Schlenk technique; Inert atmosphere
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