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[ CAS No. 10488-87-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 10488-87-6
Chemical Structure| 10488-87-6
Chemical Structure| 10488-87-6
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Product Details of [ 10488-87-6 ]

CAS No. :10488-87-6 MDL No. :MFCD00026882
Formula : C12H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RAWGHPXIJSCHFZ-UHFFFAOYSA-N
M.W : 206.24 Pubchem ID :139166
Synonyms :

Calculated chemistry of [ 10488-87-6 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.15
TPSA : 43.37 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) : -5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 2.07
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 2.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.408 mg/ml ; 0.00198 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.153 mg/ml ; 0.000743 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.27
Solubility : 0.111 mg/ml ; 0.000538 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 10488-87-6 ]

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

Application In Synthesis of [ 10488-87-6 ]

* 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 [ 10488-87-6 ]

[ 10488-87-6 ] Synthesis Path-Downstream   1~49

  • 1
  • [ 51304-64-4 ]
  • [ 10488-87-6 ]
  • [ 132856-92-9 ]
  • 2
  • [ 2985-33-3 ]
  • [ 920-39-8 ]
  • [ 10488-87-6 ]
YieldReaction ConditionsOperation in experiment
With tetrahydrofuran anschliessend Umsetzen mit Benzoylchlorid;
  • 3
  • [ 94-02-0 ]
  • [ 74-88-4 ]
  • [ 10488-87-6 ]
YieldReaction ConditionsOperation in experiment
97% To a solution of beta-keto ester (31, 10 g, 1.0 eq) in anhydrous DMF, under argon atmosphere (100 mL), anhydrous Li2CO3 (2.50 eq) was added in one portion. The reaction mixture was stirred at RT for about 10 minutes. Methyl iodide (2.50 eq) was added dropwise and the resulting suspension was stirred at 50 C. The reaction progress was monitored by TLC and HPLC. The starting material disappeared in about 17-24 h. After completion, the reaction mixture was quenched carefully by pouring into water (200 mL) containing con. HCl (20 mL). The aqueous layer was extracted with ether (2×150 ml) and the organic layer was washed with water (2×100 mL), dried (anhydrous Na2SO4) and concentrated under vacuum to furnish the crude product as viscous oil. The pure product, 2-methyl-alpha-ketoester was obtained as a colorless oil by flash chromatography on Sio2 using hexane-ether mixture as the eluent. Compund 22 (1R=phenyl, 4R=methyl, 5RH, 0R=ethyl), Ethyl-2-methyl-benzoylacetate (10.30 g, 97% yield, reference: KE-II-147): Rf 0.70 (ether/hexane, 2:8, v/v); H1NMR (CDCl3) delta 1.20 (t, 3H, COOEt), 1.50 (d, 3H, CH3), 4.15 (q, 2H, COOEt), 7.40-7.65 (m, 3H, aromatic H), 8.0 (d, 2H, aromatic H).
  • 4
  • [ 593-85-1 ]
  • [ 10488-87-6 ]
  • [ 4987-28-4 ]
YieldReaction ConditionsOperation in experiment
25% With sodium ethanolate; In ethanol; at 80℃; for 16h;Inert atmosphere; To a suspension of guanidine carbonate (199 mg, 2.21 mmol) in ethanol (22 mL) were addedethyl 2-methyl-3-oxo-3-phenylpropanoate 15 (380 mg, 1.84 mmol) and sodium ethoxide solution(25%; 1.00 mL, 3.69 mmol). The reaction mixture was heated at 80 C for 16 h, cooled toambient temperature and concentrated under reduced pressure to approximately 5 mL. Water (20mL) was added and the resulting precipitate collected by filtration and triturated with water (5ml) and methanol (5 mL) to give the title compound as a colourless solid (94 mg, 25%); mp 256-257 C (lit.,7 mp 271-273 C); (Found: M+H+, 202.0985. C11H12N3+ requires 202.0975); numax(CHCl3)/cm-1 3693, 3607, 2919, 1717, 1638, 1601, 1514, 1348, 1242, 1061, 988; deltaH (400 MHz;DMSO-d6) 7.50-7.47 (5 H, m, ArH), 6.92 (2 H, br s, NH2), 1.81 (3 H, s, Me); deltaC (100 MHz;DMSO-d6) 163.2 (C), 155.2 (C), 152.7 (C), 136.2 (C), 129.1 (CH), 128.5 (CH), 128.2 (CH),108.1 (C), 11.7 (Me); m/z (ESI) 202 (M+H+, 100%).Spectroscopic data in agreement with those previously reported.7
  • 8
  • [ 6919-61-5 ]
  • [ 105-37-3 ]
  • [ 10488-87-6 ]
  • 9
  • Ethyl 2-(benzoylthio)propanoate [ No CAS ]
  • [ 10488-87-6 ]
  • 10
  • [ 1450-93-7 ]
  • [ 10488-87-6 ]
  • [ 106263-62-1 ]
  • 13
  • [ 10488-87-6 ]
  • [ 101328-07-8 ]
YieldReaction ConditionsOperation in experiment
95% With samarium (III) iodide; iodine; In tetrahydrofuran; water; at 25℃; for 8h;Green chemistry;Catalytic behavior; General procedure: A mixture of the beta-dicarbonyl compounds (2 mmol), I2 (0.02-0.04 mmol, 1-2 mol%), and SmI3 (0.1mmol, 5 mol%) in THF (10 mL) and H2O (2 mL) were stirred at 25 C under air for the givent imes. Upon completion of the reaction (detected by TLC), the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:10~1:5) to provide the corresponding products (See below for characterization data of the products).
  • 14
  • [ 2449-05-0 ]
  • [ 10488-87-6 ]
  • (+)-1-[(1S)-1-benzoyl-2-ethoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-dibenzyl ester [ No CAS ]
  • (-)-1-[(1R)-1-benzoyl-2-ethoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-dibenzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3'-dibromo-1,1'-bi-2-naphthol; lithium hydroxide; In diethyl ether; at -23℃; for 24h;Inert atmosphere; General procedure: To a suspension of (R)-3,3?-Br2-BINOL (3a, 22.2 mg, 0.05 mmol) and LiOH (12.0 mg, 0.5 mmol) in diethyl ether (1 mL) was added a diethyl ether solution of beta-keto ester 1 (0.25 M, 2 mL, 0.50 mmol) at 23 C under an argon atmosphere. The reaction mixture was cooled to the desired temperature, and then a solution of azodicarboxylate 2 in diethyl ether (0.525 M, 1 mL, 0.525 mmol) was added. The mixture was further stirred for 24 h at the same temperature. The reaction was quenched with aqueous saturated NH4Cl (5 mL), and the aqueous layer was extracted with ethyl acetate (3 × 10 mL). The combined organic layer was washed with brine (15 mL) and then dried over Na2SO4. Concentration and column chromatographic purification gave the corresponding adduct 4. The enantiomeric excess was determined by HPLC equipped with a chiral column.
  • 15
  • [ 4407-36-7 ]
  • [ 10488-87-6 ]
  • ethyl (E)-2-benzoyl-2-methyl-5-phenylpent-4-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); acetic acid; In neat (no solvent); at 100℃; for 8h;Reflux; General procedure: To a 50 mL round-bottle flask was added ethyl 3-(4-methoxyphenyl)-2-methyl-3-oxopropanoate(1.00 g, 4.25 mmol), acetone (8 mL), 3-chloro-2-methylprop-1-ene (0.50 mL, 5.1 mmol), K2CO3(0.880 g, 6.4 mmol) and NaI (0.156 g, 1.1 mmol). The reaction mixture was refluxed for 24 h, thenfiltered and evaporated. H2O (10 mL) was added and the mixture was extracted with AcOEt (20mL x 3). The combined organic layer was washed with brine (15 mL), the dried over MgSO4,filtered and evaporated. The residue was subjected to silica gel column chromatography(hexane/AcOEt = 10:1) to afford ethyl 2-(4-methoxybenzoyl)-2,4-dimethylpent-4-enoate as paleyellow oil (0.795 g, 2.74 mmol) in 64% yield. To a 50 mL round-bottle flask was added ethyl 2-(4-methoxybenzoyl)-2,4-dimethylpent-4-enoate(0.795 g, 2.74 mmol), NH2OH·HCl (0.571 g, 8.22 mmol), NaOAc (0.227 g, 2.74 mmol), EtOH (4.5mL) and H2O (0.9 mL). The reaction mixture was refluxed for 3 days, then 12 N HClaq (0.91 mL)was added to the mixture and refluxed for more 30 minutes. After cooling to rt, H2O (5 mL) wasadded and the reaction mixture was extracted with AcOEt (20 mL x 3). The combined organiclayer was washed with brine (15 mL), the dried over MgSO4, filtered and evaporated. The residuewas subjected to silica gel column chromatography (hexane/AcOEt = 8:1) to afford3-(4-methoxyphenyl)-4-methyl-4-(2-methylallyl)isoxazol-5(4H)-one as an orange solid (0.426 g,1.64 mmol) in 60 % yield.
  • 16
  • [ 154385-24-7 ]
  • [ 10488-87-6 ]
  • ethyl 2-benzoyl-2-methyl-3-methylene-7-methoxyheptanoate [ No CAS ]
  • 17
  • [ 10488-87-6 ]
  • (2S,3R)-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester [ No CAS ]
  • 18
  • [ 609-14-3 ]
  • [ 4231-62-3 ]
  • [ 18773-93-8 ]
  • [ 10488-87-6 ]
  • 19
  • [ 74-86-2 ]
  • [ 10488-87-6 ]
  • ethyl 2-ethenyl-2-methyl-3-oxobenzenepropanoate [ No CAS ]
  • 20
  • [ 629-05-0 ]
  • [ 10488-87-6 ]
  • ethyl 2-methyl-3-methylene-2-phenylcarbonylnonanoate [ No CAS ]
  • 21
  • [ 536-74-3 ]
  • [ 10488-87-6 ]
  • ethyl 2-methyl-3-phenyl-2-phenylcarbonyl-3-butanoate [ No CAS ]
  • 23
  • [ 99-88-7 ]
  • [ 7440-44-0 ]
  • [ 10488-87-6 ]
  • [ 328396-64-1 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride; PPA; In methanol; ethanol; Step 1. 2-phenyl-3-methyl-6-isopropyl-1,4-dihydro-4-oxoquinoline To polyphosphoric acid (1.5 g) heated to 160 C. were added dropwise a solution of 4-isopropylaniline(0.5 g, 3.6 mmol) and <strong>[10488-87-6]ethyl 2-benzoylpropionate</strong> (1.52 g, 7.3 mmol) in ethanol with stirring. The mixture was stirred at 160 C. for 3 hours. After cooling, a cold solution of 10% hydrochloric acid was added to the mixture. The resulting precipitate was recovered by filtration, dissolved in methanol and treated with active carbon. After evaporating in vacuo, the residue was recrystallized from ethyl acetate to give the title compound in a yield of 81%. 1H-NMR(DMSO-d6)delta 1.28(6H,d,CH(CH3)2), 2.0(3H,s,CH3), 3.07(1H,septet,CH), 7.61(5H,s,Ar-H), 7.6-7.7(2H,m,H-7,8), 8.13(1H,s,H-5), 12.67(1H,s,NH)
  • 24
  • [ 623-73-4 ]
  • [ 5908-41-8 ]
  • [ 74-88-4 ]
  • [ 10488-87-6 ]
  • 25
  • [ 85515-56-6 ]
  • [ 74-88-4 ]
  • [ 10488-87-6 ]
  • 26
  • [ 932-88-7 ]
  • [ 10488-87-6 ]
  • [ 1016893-06-3 ]
  • 28
  • [ 93-55-0 ]
  • [ 105-58-8 ]
  • [ 10488-87-6 ]
YieldReaction ConditionsOperation in experiment
51% With sodium hydride; In toluene; at 70℃;Inert atmosphere; General procedure: A suspension of sodium hydride (60%; 3 eq) and diethyl carbonate (3 eq) in anhydrous toluene(10 mL/mmol) under argon was heated to 70 C and the aryl methyl ketone (3.76-13.3 mmol)added dropwise if liquid, or as a solution in toluene (1 mL/mmol) if solid. The reaction mixturewas heated at 70 C for 1-16 h, cooled to ambient temperature and acetic acid (1 mL) addeddropwise. Ice-water (20 mL) was added and the layers separated. The aqueous layer wasextracted with ethyl acetate (3 x 20 mL), and the organic extracts combined and washed withwater (40 mL) and saturated brine (40 mL), dried (MgSO4) and concentrated under reducedpressure. Purification by column chromatography gave the title compound.
Preparation Example 1; [Show Image] Sodium hydride (60% w/w, 10.0 g, 250 mmol, 2.5 eq.) was suspended in dry toluene (50 mL) and diethyl carbonate (24.4 mL, 200 mmol, 2.0 eq.) was added. The resulting suspension was heated to 80 C and subsequently propiophenone (13.4 mL, 100 mmol, 1.0 eq.) was added over 1 hour using a syringe pump. The mixture was cooled to room temperature and then poured into ice-water (150 mL) containing glacial acetic acid (25 mL). The organic layer was separated and the aqueous layer was extracted with MTBE (200 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give the desired beta-ketoester 1 as a yellowish liquid. The product was used in the next step without further purification. 1H-NMR of 1 (CDCl3, 300 MHz) delta = 1.17 (t, 3H, J = 7.2 Hz), 1.50 (d, 3H, J = 6.9 Hz), 4.18 (q, 2H, J = 7.2 Hz), 4.38 (q, 1H, J = 6.9 Hz), 7.48 (m, 2H), 7.58 (m, 1H), 7.99 (d, 2H, J = 7.2 Hz) ppm.
  • 29
  • [ 10488-87-6 ]
  • [ 106815-16-1 ]
  • [ 106815-12-7 ]
YieldReaction ConditionsOperation in experiment
General procedure: Ni(ClO4)2·6H2O (10mol%) and ligand 5 (12mol%) were stirred in a dried flask under vacuum for 2h at room temperature, and then 4 molecular sieves (50mg) and dry CH2Cl2 (2mL) were added under argon atmosphere and stirred for 1h. Substrate 6 (0.25mmol) was added to the flask. After stirring for 30min at -60C, N-fluorobenzenesulfonimide (NFSI; 1.2equiv.) was added directly to the mixture at -60C. The reaction mixture was stirred at -60C for 14h, and then warmed to room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography using petroleum ether:ethyl acetate=6:1 as eluent to obtain the desired products 7a-p.
  • 30
  • [ 33252-32-3 ]
  • [ 10488-87-6 ]
  • [ 1204429-26-4 ]
  • 32
  • [ 57-13-6 ]
  • [ 10488-87-6 ]
  • [ 25796-67-2 ]
YieldReaction ConditionsOperation in experiment
76% With boron trifluoride diethyl etherate; at 145℃; for 0.116667h;Neat (no solvent); Microwave irradiation; General procedure: Ethyl 3-oxo-3-phenylpropanoate (384mg, 2mmol) taken in a reactor vessel with BF3 Et2O (339mg, 2.4mmol) was mixed thoroughly for 1 min with urea (156 mg, 2.6mmol). The vessel was closed immediately and was subjected to microwave irradiation for about 4 min at about 145C. The compound (6) was further purified by column chromatography. Yeild: 92%
  • 33
  • [ 10488-87-6 ]
  • [ 753030-96-5 ]
  • (R)-ethyl 2-chloro-2-methyl-3-oxo-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one; 2CF3O3S(1-)*C50H45NOP2Pd(2+); In dichloromethane; at -20℃; for 36h; Typical procedure: To a stirred solution of tert-butyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate (1c, 464 mg, 2.0 mmol), Pd-cat. 4d (11.1 mg, 0.01 mmol) in DCM (8 mL) at -20 C was slowly added 2,3,4,5,6,6-hexachlorocyclohexa-2,4-dienone (2, 722 mg, 2.4 mmol) in DCM (4 mL). The reaction mixture was stirred for 10 h at -20 C, then the reaction mixture was evaporated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel to give the alpha-chlorinated beta-keto ester 3c (93%, 496 mg).
  • 34
  • [ 15108-18-6 ]
  • [ 10488-87-6 ]
  • [ 1453097-53-4 ]
YieldReaction ConditionsOperation in experiment
In acetic acid; at 20℃; for 2h; General procedure: A mixture of 2-hydrazino-5-methyl-benzimidazole (3, 1.0g, 6.17mmol) and ethyl 2-acetyl-3-phenylpropanoate (4, 1.4mL, 6.59mmol) in acetic acid (20mL) was stirred for 2h at ambient temperatures. To a mixture of acetonitrile (100mL) and water (100mL) was added the reaction mixture. After stirring at ambient temperatures, the resulting precipitates were collected by filtration and washed with acetonitrile in water (1:1). The precipitates was purified by recrystallization from ethanol (95mL) to generate 3-methyl-1-(5-methyl-1H-benzimidazol-2-yl)-4-benzyl-1H-pyrazol-5-ol (35, 0.64g, 32.6%). The other compounds studied in this work (5-52) were prepared in a similar manner. The typical experimental procedure for synthesizing and evaluating the compounds used in this study, in addition to the analytical data and the estimated purity (HPLC) of the biologically relevant compounds, are provided in Supplemental data and Table S1, respectively.
  • 35
  • C6H11NO5 [ No CAS ]
  • [ 10488-87-6 ]
  • C17H23NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With tert.-butylhydroperoxide; magnesium chloride; In decane; acetonitrile; at 40℃; for 49h; General procedure: TBHP (5-6 M in decane, 0.48 mmol) was added dropwise to a mixture of beta-ketoesters 1 (0.48 mmol), hydroxamic acids 2(0.40 mmol), and MgCl2 (3.8 mg, 0.040 mmol) in MeCN (2mL). The reaction was stirred at 40 C for the indicated time;reaction completion was confirmed based on thedisappearance of hydroxamic acids (Table 2). Then thereaction mixture was cooled to r.t., quenched with aqNaHSO3 solution and extracted with CH2Cl2 three times.The combined organic layers were dried over anhydrousNa2SO4, filtered, and then concentrated in vacuo. The residue was purified by column chromatography to afford amination product 3. This General Experimental Procedure was carried out using 1a (69.2 mg, 0.48 mmol) and 2a (53.2mg, 0.40 mmol). The reaction mixture was stirred for 34 h at 40 C and purified by silica gel chromatography using PE-CH2Cl2-EtOAc (4:1:0.75) as eluent to give product 3a (94.3mg, 85%) as a colorless oil. The structure of 3a was identified by comparison of its 1H NMR and 13C NMR spectra with the reported data in ref. 8. See the Supporting Information for experimental details and characterization data for all new compounds.
  • 36
  • 2-((trifluoromethyl)thio)benzo[d]isothiazol-3(2H)-one 1,1-dioxide [ No CAS ]
  • [ 10488-87-6 ]
  • ethyl 2-methyl-3-oxo-3-phenyl-2-((trifluoromethyl)thio)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With dmap; In toluene; at 20℃; for 8h; Methyl-3-oxo-3-phenylpropionic acidEthyl ester (61.8 mg, 0.3 mmol)And trifluoromethylthio reagent (100 mg, 0.36 mmol)And dimethylaminopyridine (DMAP) (73 mg, 0.60 mmol) were dissolved in toluene (6.0 ml) and reacted at room temperature for 8 hours. After completion of the reaction, the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by flash silica gel column to give the corresponding product c1 (87 mg, 95%). Purity was identified by the H-spectrum95%.
  • 37
  • [ 614-45-9 ]
  • [ 94-02-0 ]
  • [ 10488-87-6 ]
YieldReaction ConditionsOperation in experiment
75% With acetic acid; copper(l) chloride; at 120℃; In order to 3-(phenyl)oxopropanoic acid ethyl ester, tert-butyl peroxybenzoate is used as a raw material, the reaction steps are as follows:In the reaction flask by adding 3-(phenyl)oxopropanoic acid ethyl ester (0.19g, 1mmol), tert-butyl peroxybenzoate (0.58g, 3mmol), CuCl (0.01g, 0 . 1mmol) and 2 ml acetic acid, 120 C reaction;TLC until the complete end tracking of the reaction;After the reaction the crude product by column chromatography (petroleum ether: ethyl acetate = 40:1), to obtain the target product (yield 75%).
  • 38
  • [ 36719-40-1 ]
  • [ 10488-87-6 ]
  • C18H18N2O3 [ No CAS ]
  • 39
  • [ 216661-87-9 ]
  • [ 10488-87-6 ]
  • 6-methyl-5-phenyl-3-(4-pyridyl)-4H-pyrazolo[1,5-a]pyrimidin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.4% With sulfuric acid; In ethanol; at 80℃; for 24h; A mixture of 4-(4-pyridyl)-1H-pyrazol-5-amine (100 mg, 0.624 mmol), <strong>[10488-87-6]ethyl 2-methyl-3-oxo-3-phenyl-propanoate</strong> (193 mg, 0.936 mmol) and H2SO4 (191 mg, 1.87 mmol) in EtOH (2 mL) was heated at 80 C. for 24 h. The mixture was cooled to room temperature. A precipitate formed and was collected by filtration. The filter cake was washed with ether, dried under vacuum to give the title compound (112 mg, 59.4% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 8.50 (s, 1H), 8.40 (d, J=6.35 Hz, 2H), 8.20 (s, 2H), 7.62-7.54 (m, 2H), 7.53-7.39 (m, 3H), 6.54 (s, 1H), 1.99 (s, 3H). LCMS (ESI) m/z 303 [M+H+].
  • 40
  • [ 106-41-2 ]
  • [ 10488-87-6 ]
  • ethyl 2-(4-bromophenoxy)-2-methyl-3-oxo-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 1,10-Phenanthroline; iron (III) perchlorate monohydrate; di-tert-butyl peroxide; 1,1,1,3',3',3'-hexafluoro-propanol; at 20℃; for 24h; General procedure: t-BuOO-tBu (2.5 equiv) was added dropwise with constant stirring to a solution of the appropriate halophenol 1 (1.0 equiv), the alpha-substituted beta-keto ester (1.5 equiv), 1,10-phenanthroline (10 mol %), and Fe(ClO4)3·nH2O (10 mol %) in (F3C)2CHOH (1 M) at r.t. The mixture was stirred at r.t. for 24 h until the halophenol was completely consumed (HPLC; lambda = 210 nm). Volatiles were removed under reduced pressureand the crude residue was purified by column chromatography.
  • 41
  • [ 544-97-8 ]
  • [ 94-02-0 ]
  • [ 10488-87-6 ]
  • 42
  • [ 3360-54-1 ]
  • [ 10488-87-6 ]
  • ethyl 2-benzoyl-2-methyl-4-phenylpent-4-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% To a flamed-dried 50 mL two-necked round-bottle flask was added NaH (60% in mineral oil,0.242 g, 6.0 mmol) and THF (10 mL). Ethyl 2-methyl-3-oxo-3-phenylpropanoate (1.03 g, 5.0mmol) was added to the reaction mixture at 0 C and the mixture was stirred for 30 min at the sametemperature. Then (3-bromoprop-1-en-2-yl)benzene (1.38 g, 7.0 mmol) was added. After stirredat rt for 20 h, the mixture was quenched by saturated NH4Cl aq (7 mL), then extracted with AcOEt (7mL × 4). The combined organic layer was washed with brine (15 mL), then dried over MgSO4,filtered and evaporated. The residue was subjected to silica gel column chromatography(hexane/AcOEt = 25:1) to afford ethyl 2-benzoyl-2-methyl-4-phenylpent-4-enoate as pale yellow oil(1.17 g, 3.65 mmol) in 73% yield.
  • 43
  • [ 83126-01-6 ]
  • [ 10488-87-6 ]
  • ethyl (E)-2-benzoyl-2,4-dimethyl-5-phenylpent-4-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a flamed-dried 50 mL two-necked round-bottle flask was added NaH (60% in mineral oil,0.242 g, 6.0 mmol) and THF (10 mL). Ethyl 2-methyl-3-oxo-3-phenylpropanoate (1.03 g, 5.0mmol) was added to the reaction mixture at 0 C and the mixture was stirred for 30 min at the sametemperature. Then (3-bromoprop-1-en-2-yl)benzene (1.38 g, 7.0 mmol) was added. After stirredat rt for 20 h, the mixture was quenched by saturated NH4Cl aq (7 mL), then extracted with AcOEt (7mL × 4). The combined organic layer was washed with brine (15 mL), then dried over MgSO4,filtered and evaporated. The residue was subjected to silica gel column chromatography(hexane/AcOEt = 25:1) to afford ethyl 2-benzoyl-2-methyl-4-phenylpent-4-enoate as pale yellow oil(1.17 g, 3.65 mmol) in 73% yield.
  • 44
  • [ 870-50-8 ]
  • [ 10488-87-6 ]
  • (-)-1-[1-benzoyl-2-ethoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butyl ester [ No CAS ]
  • (+)-1-[1-benzoyl-2-ethoxy-1-methyl-2-oxoethyl]-1,2-hydrazinedicarboxylic acid 1,2-di-tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3'-dibromo-1,1'-bi-2-naphthol; lithium hydroxide; In diethyl ether; at -60℃; for 24h;Inert atmosphere; To a suspension of (R)-3,3'-Br2-BINOL (22.2 mg, 0.05 mmol) and LiOH (12.0 mg, 0.5 mmol) in Et2O (1 mL) wasadded an Et2O solution of beta-keto ester 1a (0.25 M, 2 mL, 0.50 mmol) at room temperature under argon atmosphere. Asolution of azodicarboxylate 2x in Et2O (0.525 M, 1 mL, 0.525 mmol) was added at -60 C to the reaction mixture,which was further stirred for 24 hours at the same temperature. The reaction was quenched with aqueous saturatedNH4Cl (5 mL), and the aqueous layer was extracted with EtOAc (3 x 10 mL). The combined organic layers werewashed with saturated NaCl (15 mL), and dried over Na2SO4. Concentration and column chromatographic purificationgave the corresponding adduct 3ax in 90% yield with 87% ee.
General procedure: In an open-air tube at room temperature (25 C) the corresponding 1,3-dicarbonyl compound(0.1 mmol) was added to a solution of organocatalyst (0.01 mmol, 10 mol %) in toluene (1 mL).After 5 min, di-tert-butylazodicarboxilate (0.11 mmol, 1.1 equiv.) was added in one portion and thereaction was then allowed to react for 15 h. After this time, water (5 mL) and ethyl acetate were added,and then the aqueous layer was re-extracted twice (2 x 10 mL). The combined organic phases weredried (MgSO4) and evaporated under reduced pressure. Finally, the reaction crude was purified bycolumn chromatography on silica gel or preparative TLC using hexane/ethyl acetate mixtures aseluent. The analytical data shown below correspond to those enantioenriched products (20% ee)as representative compounds. All the compounds are described in the literature. Therefore, only1H-NMR, MS (EI) and enantiomeric excess determination conditions are listed.
General procedure: In an open-air tube at room temperature (25 C) the corresponding 1,3-dicarbonyl compound(0.1 mmol) was added to a solution of organocatalyst (0.01 mmol, 10 mol %) in toluene (1 mL).After 5 min, di-tert-butylazodicarboxilate (0.11 mmol, 1.1 equiv.) was added in one portion and thereaction was then allowed to react for 15 h. After this time, water (5 mL) and ethyl acetate were added,and then the aqueous layer was re-extracted twice (2 x 10 mL). The combined organic phases weredried (MgSO4) and evaporated under reduced pressure. Finally, the reaction crude was purified bycolumn chromatography on silica gel or preparative TLC using hexane/ethyl acetate mixtures aseluent. The analytical data shown below correspond to those enantioenriched products (20% ee)as representative compounds. All the compounds are described in the literature. Therefore, only1H-NMR, MS (EI) and enantiomeric excess determination conditions are listed.
  • 45
  • [ 10357-84-3 ]
  • [ 10488-87-6 ]
  • 7-hydroxy-4-phenyl-2H-pyrano[2,3-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trans-Decalin; triethylamine at 170℃; for 12h; 24 Example 25 Example 25: 3,6-dimethyl-5-phenyl-7H-furo[2,3-b]pyrano[3,2-e]pyridin-7-one (cf Scheme 6) This compound was synthesized in analogy to Example 24, using the appropriate β-ketoester ethyl 2-methyl-3-oxo-3-phenyl-propanoate (b4) and pyridine-2,6-diol hydrochloride (r2) in the first reaction step (heating was extended to 12 h). Overall yield: 3%. Intermediate 3-methyl-7-(2-oxopropoxy)-4-phenyl-2H-pyrano[2,3-bjpyridin-2-one H NMR (300 MHz, CDCI3): δ = 1.96 (3H, s, Me), 2.25 (3H, s, Me), 5.02 (2H, s, CH2), 6.71 (1H, d, Ar-H), 7.18-7.22 (2H, m, Ar-H), 7.32 (1H, d, Ar-H), 7.45-7.57 (3H, m, Ar-H). Title compound: 1H NMR (300 MHz, CDCI3): δ = 2.01 (3H, s, Me), 2.13 (3H, d, Me), 7.26- 7.30 (2H, m, Ar-H), 7.46-7.48 (2H, m, Ar-H), 7.52-7.63 (3H, m, Ar-H); [M+H]+ (HPLC/MS): 291 ,83.
  • 46
  • [ 7357-70-2 ]
  • [ 10488-87-6 ]
  • 2-mercapto-5-methyl-6-oxo-4-phenyl-1,6-dihydropyridine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
600 mg To a solution of 2-cyanoethanethioamide (534 mg, 5.335 mmol) in EtOH (10 mL) wasadded EtONa (4.6 ml, 7.3 mmol, 1.5 Min EtOH) at 60 C. Then the mixture was stirred at60 C for 1 h. Then ethyl2-methyl-3-oxo-3-phenylpropanoate (1 g, 4.85 mmol) was added.The mixture was warmed to 90 C and stirred for 3 h. The reaction mixture was cooled toroom temperature, poured into water (50 mL), and extracted with EtOAc (3X50 ml). Theorganic layers were discarded. The aqueous layer was acidified to pH=3-5 by addition of 1 N HCl and extracted with EtOAc (3X50 mL), the combined organic layers were washedwith brine, dried over Na2S04, filtered, and evaporated in vacuo to get the crude titlecompound (600 mg) which was directly used in the next step. LC-MS (ESI+): m/z 243.0(M+Ht.
  • 47
  • [ 10488-87-6 ]
  • ethyl 2-bromo-2-methyl-3-oxo-3-phenylpropanoate [ No CAS ]
  • ethyl 2-bromo-2-methyl-3-oxo-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: 100 mg of Molecular Sieve 4A (MS 4 A) was placed in a branched eggplant flask,After drying under vacuum at 140 C. for 24 hours, it was cooled and 1.0 mg (0.0025 mmol) of nickel perchlorate hexahydrate,(0.044 mmol) of (R, R) -4,6-dibenzofuranediyl-2,2'-bis (4-phenyloxazoline) [(R, R) - DBFOX - Ph] was added, And dried for 2 hours.After purging with nitrogen, 1 mL of dry dichloromethane was added and the mixture was stirred at room temperature for 1 hour.41.4 mg (0.2 mmol) of ethyl 2-methyl-3-oxo-3-phenylpropanoate was dissolved in dry dichloromethane (1 mL × twice) and stirred at room temperature for 0.5 hour. 42.7 mg (0.24 mmol) of N-bromosuccinimide (NBS) was added, and the mixture was stirred at room temperature for 120 hours.5 mL of 0.5 M sodium thiosulfate aqueous solution was added and the mixture was extracted with dichloromethane (5 mL × 4 times). The organic layer was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain a pale yellow solid.The obtained crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 40/1, v / v)22.3 mg (yield 39%) of the objective 2-bromo-2-methyl-3-oxo-3-phenylpropanoate was obtained as a colorless oily substance.As a result of the analysis, the enantiomeric excess was 76% ee (R). The results are shown in Table 1.
100 mg of Molecular Sieve 4A (MS 4 A) was placed in a branched eggplant flask,After drying under vacuum at 140 C. for 24 hours, it was cooled and 1.0 mg (0.0025 mmol) of nickel perchlorate hexahydrate,(0.044 mmol) of (R, R) -4,6-dibenzofuranediyl-2,2'-bis (4-phenyloxazoline) [(R, R) - DBFOX - Ph] was added, And dried for 2 hours.After purging with nitrogen, 1 mL of dry dichloromethane was added and the mixture was stirred at room temperature for 1 hour.41.4 mg (0.2 mmol) of ethyl 2-methyl-3-oxo-3-phenylpropanoate was dissolved in dry dichloromethane (1 mL × twice) and stirred at room temperature for 0.5 hour. 42.7 mg (0.24 mmol) of N-bromosuccinimide (NBS) was added, and the mixture was stirred at room temperature for 120 hours.5 mL of 0.5 M sodium thiosulfate aqueous solution was added and the mixture was extracted with dichloromethane (5 mL × 4 times). The organic layer was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain a pale yellow solid.The obtained crude product was purified by silica gel column chromatography (hexane / ethyl acetate = 40/1, v / v)22.3 mg (yield 39%) of the objective 2-bromo-2-methyl-3-oxo-3-phenylpropanoate was obtained as a colorless oily substance.As a result of the analysis, the enantiomeric excess was 76% ee (R). The results are shown in Table 1.
  • 48
  • [ 2468-55-5 ]
  • [ 10488-87-6 ]
  • (±)-ethyl 2-benzoyl-2-methylhept-6-ynoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: ethyl 2-benzoylpropionate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Stage #2: 5-iodopent-1-yne In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil
  • 49
  • [ 382-14-9 ]
  • [ 10488-87-6 ]
  • C16H16F6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N,N,N-tributylbutan-1-aminium fluoride In tetrahydrofuran at -20℃; for 1.5h;
Same Skeleton Products
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