Name: 2169-69-9|(E)-Ethyl 2-cyano-3-phenylacrylate|95%
Brand: Ambeed
SKU: A704285
Price: 19.0 USD
Availability: InStock
Rating: 99 (30 reviews)

1
[ 100-52-7 ]
[ 105-56-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tetreamethyl ammonium hydroxide at 60℃; for 0.5h;
100%	With <i>L</i>-proline for 0.0833333h; microwave irradiation;
100%	In toluene at 80℃; for 8h;

100%	With 1-(3-silica-supported propyl)-3-[(3-[1-(3-silica-supported propyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl]methyl}-2,4,6-trimethylphenyl)methyl]-4,5-dihydro-1H-imidazol-3-ium chloride at 130℃; for 2h;
100%	With ethylenediamine-modified poly(vinyl chloride) at 20℃; for 0.1h; Green chemistry;
100%	With UiO-67-NH₂-L₂; [Zr₆(μ₃-O)₄(μ₃-OH)₄(1,4-benzenedicarboxylate)₆][(S)-N-(tert-butyl)-1-((6-formylpyridin-2-yl)methyl)pyrrolidine-2-carboxamide]-NH₂ In toluene at 100℃; for 6h;
99%	at 39.85℃; for 7h;
99%	With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.25h;
99%	With (H3O)2[Cd3(9H-carbazole-2,7-dicarboxylic acid(-2H))4]·3DMF·4H2O In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;
99%	With ZIF-8/NaA/PSS composite membrane microreactor In dimethyl sulfoxide at 40℃; for 0.333333h; Flow reactor;	2.2 Catalytic performance tests Knoevenagel condensation between BA and ECA was carried out in a continuous flow MMR plant as showed in Fig. S1. The reactant mixture with equimolar BA and ECA dissolved in dimethyl sulfoxide (DMSO) as solvent was fed using a microflow pump (BT50-1J, Baoding Longer Precision Pump Co., Ltd.). The reaction mixture was collected and analyzed by gas chromatography (GC7890F, Shanghai Techcomp Ltd.) using a HP-5 column (30m×320μm×0.25μm, Agilent) and flame ionization detector.
99%	With mesoporous basic Mg-Al mixed metal oxides⁽¹²⁾-F₁₂₇ In toluene at 60℃; for 0.166667h; Inert atmosphere; Schlenk technique;
98%	In lithium hydroxide monohydrate at 50℃; for 44h;
98.9%	With 3-(1-pirerazino)propyl-functionalised silica gel In acetonitrile at 20℃; electroosmotic flow;
98%	In various solvent(s) at 20℃; for 4h;
98%	With ASCPEI In ethanol at 43℃; for 2h;
98%	With polyacrylonitrile fiber modified with triethylenetetramine In lithium hydroxide monohydrate at 50℃; for 1.5h;
98%	With GeH₂O₃₄W₁₀^(6-)*6C₁₆H₃₆N⁽¹⁺⁾ In acetonitrile at 39.84℃; for 0.0833333h;
98%	With lysine immobilized on zeolite 4A In neat (no solvent) at 20℃; for 0.166667h; Green chemistry;	General Procedure for Knoevenagel Condensation Reaction General procedure: In a typical procedure, a mixture of benzaldehyde (2mmol), ethyl cyanoacetate (2 mmol) and modified Lys/zeolite 4A (0.1 g) was placed in a round bottom flask. The suspension was agitated at room temperature for 10 minutes. Completion of the reaction was monitored by TLC, using n-hexane/ethyl acetate (5:1) as eluent. For the reaction workup, the catalyst was removed by filtration and washed with hot ethanol. Then, the solvent was evaporated and a pure product was obtained. The products were identified using 1H-NMR, 13C-NMR and FT-IR spectroscopy techniques. Quantitative analyses were conducted with an Agilent 6820 GC equipped by gas chromatography (GC) using a HP 5890 Series II Chromatograph fitted with a packed column (18% Carbowax 20 M/Chromosorb W AW-DMCS), equipped with an HP 5971 Mass Selective Detector.
98%	With 1-[2-(2-hydroxyethoxy)ethyl]-1,5-diazabicyclo[4.3.0]non-5-ene chloride In neat (no solvent) at 20℃; for 0.333333h; Green chemistry;	General procedure for Knoevenagel condensation General procedure: A round bottom flask was charged with aryl aldehyde (10 mmol), 2,4-thiazolidinedione (10 mmol) and ionic liquid (2 mmol). The reaction mixture was stirred and monitored by TLC. Upon completion, water was added and the mixture was stirred. The mixture was allowed to stand to separate into two layers, affording the product and ionic liquid. The separated solid product was suction-filtered and further purified by crystallization from hot EtOH. The filtrate containing the ionic liquid was then evaporated under reduced pressure, and the ionic liquid was reused directly for the next run. The melting point and spectra data of products are given as below.
98%	With C₇H₁₅N₄⁽¹⁺⁾*BF₄^(1-) In lithium hydroxide monohydrate at 20℃; for 0.0833333h; Green chemistry;	General procedure for Knoevenagel condensation General procedure: To a well stirred mixture of carbonyl compound, 1 (2.0 mmol) and active methylene compound, 2 (2.0 mmol), ionic liquid [MeHMTA]BF4 (72.6 mg, 15 mol% of the substrate) was added and stirred at RT. The formation of the products was monitored by TLC. After completion of the reaction, the reaction mixture was filtered, washed with water (3×5 mL) and dried to obtain the products. In general, no further purification was required for solid product. However, for liquid mixture, ethyl acetate (2.0 mL) was added to the reaction mixture. The organic phase was dried with anhydrous MgSO4 and evaporated. In some cases, the crude product was purified by column chromatography over silica gel to afford the pure product. All the products were previously reported and were characterized by melting point determination, 1H and 13C NMR spectral data. The ionic liquid catalyst was recovered from water and reused for the subsequent reactions. Selected data for the products are given below.
98%	With 2C₂₁H₁₁O₆^(3-)C₄H₄N₂3Cu⁽²⁺⁾*H₂O In cyclohexane at 80℃; for 12h;
98%	With DABCO supported on SiO₂ covered Fe₃O₄ nanoparticles In lithium hydroxide monohydrate at 60℃; for 3h;	General procedure of the Knoevenagel reaction General procedure: To a stirred mixture of 5 mmol aldehyde and 6 mmol ethyl cyanoacetate or malononitrile in the solvent (2.5 mL H2O and 2.5 mL PEG-400) at 60 °C was added 0.3 g magnetic nanocatalyst (Fe3O4&SiO2&propyl&DABCO), thin layer chromatography (TLC) was used to detect the reaction. As the reaction proceeds, a large number of white solid products appear, at the end of the reaction, the crude product was separated and the magnetic nano-catalyst was further removed by a magnet. the crude product was washed with 30 mL water (10 mL x 3) and the almost pure target product was achieved.
98%	With DABCO supported on SiO₂ covered Fe₃O₄ nanoparticles In lithium hydroxide monohydrate at 60℃; for 3h; Green chemistry;	General procedure of the Knoevenagel reaction General procedure: To a stirred mixture of 5 mmol aldehyde and 6 mmol ethyl cyanoacetate or malononitrile in the solvent (2.5 mL H2O and 2.5 mL PEG-400) at 60 °C was added 0.3 g magnetic nanocatalyst (Fe3O4&SiO2&propyl&DABCO), thin layer chromatography (TLC) was used to detect the reaction. As the reaction proceeds, a large number of white solid products appear, at the end of the reaction, the crude product was separated and the magnetic nano-catalyst was further removed by a magnet. the crude product was washed with 30 mL water (10 mL x 3) and the almost pure target product was achieved.
97%	With anhydrous ammonium acetate for 0.0833333h; microwave irradiation;
97%	With 3-(1-piperazino)propyl functionalised silica gel In acetonitrile
97%	With 1H-imidazole In dichloromethane for 0.666667h; Heating;
97%	With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Reflux;
97.6%	With air; Pd₁-Au₁ bimetal catalysts supported on basic layered double hydroxide at 353℃; for 1h;
96%	With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In lithium hydroxide monohydrate at 100℃; for 0.666667h; stereoselective reaction;
96%	With diazabicyclo[5.4.0]undec-7-ene-water complex at 20℃; for 0.333333h;
96%	With [(n-C₄H₉)₄N]₈[α-Si₂W₁₈O₆₂]·3H₂O In acetonitrile at 32℃; for 3h;
96%	With IRA-96 anion-exchange resin In ethanol at 25 - 30℃; for 1h; Sonication; Green chemistry; stereoselective reaction;	2.2 General procedure for Knoevenagel condensation General procedure: Aldehyde (10mmol), the active methylene compound (10mmol), 0.20g/0.01mol is the ratio of resin and 2mL of ethanol were charged in a 10mL glass reactor. The glass was located at the maximum energy area in the ultrasonic cleaner and the addition or removal of water was used to control the temperature of the water bath at room temperature (25-30°C). After each test, the reaction mixture was filtered to recover the catalyst. It was then washed with hot ethanol (10mL). Afterwards, the sample was taken and analyzed by GC to determine the yield of the reaction.
96%	With C₈H₁₈NO₃⁽¹⁺⁾*C₂H₄NO₂^(1-) In lithium hydroxide monohydrate at 20℃;	General procedure for the Knoevenagel condensation. General procedure: A mixture of carbonyl compound (0.5 mmol), activated methylene compound (0.5 mmol), IL catalyst (10 mol %) and water (1 mL) was stirred at room temperature in 25-mL round bottomed flask. Upon completion of the reaction (monitored by TLC), the reaction mixture always solidified in the round bottomed flask. Then the solidified mixture was filtered and washed with cold water (5 mL) to remove the IL catalyst, and evaporated under reduced pressure to obtain the target products. The products of 3o, 3p, 3q, 3x, 3c’, 3d’ are colourless oil, and they were purified by column chromatography on silica gel using petroleum ether/ethyl acetate as the eluent after the solvent was removed under reduced pressure. The products of 3j’, 3k’were prepared under solvent-free condition; After completion of the reaction, the solidified mixture was washed with ethanol (5 mL) to remove the IL catalyst, and evaporated under reduced pressure to obtain the target products.
96%	With glacial acetic acid; urea In neat (no solvent) for 0.0138889h; Microwave irradiation;	General procedure for synthesis of ethyl ααααα -cyanocinna-mates (3a-n) and 5-arylidine-2,4-thiazolidinediones (5a-l): General procedure: A mixture of aromatic aldehydes (4.7 mmol), ethyl cyano-acetate (0.531 g, 4.7 mmol) or 1,3-thiazolidinone-2,4-dione(0.550 g, 4.7 mmol) and urea-acetic acid in (0.028 g : 0.028 g,10 mmol % 1:1) was taken in an Erlenmeyer flask and subjectedto microwave irradiation at 600 W at 10 s interval for a specified time as indicated in Tables 1 and 2. The completion of thereaction was monitored by TLC (20 % ethyl acetate in n-hexane).The reaction mixture was cooled to room temperature andtreated with cold water the product thus obtained was filtered,dried and recrystallized from ethanol affording pure products.Physical and spectral dataEthyl (E)-2-cyano-3-phenyl-2-propenoate (3a): Yield:96 %; m.p.: 50-51 °C (lit. 50 °C [11]); FTIR (KBr, ν max , cm -1 ):2982, 2222, 1725, 1605; 1 H NMR (400 MHz, CDCl 3 ): δ = 8.2(s, 1H, CH), 7.9 (m, 2H, phenyl), 7.5 (m, 3H phenyl), 4.3-4.4(q, J = 7.12 Hz, 2H, CH 2 ), 1.3-1.4 (t, J = 7.12 Hz, 3H, CH 3 );LC-MS: m/z (M +1) calcd. for C 12 H 11 NO 2 : 202; found: 202.
96%	With C₉H₁₆N₂*C₅H₅NO In ethanol at 25 - 30℃; for 0.333333h;	2.4. Knoevenagel reaction catalyzed by hydroxypyridine anion-based PILs The experiment of Knoevenagel reaction (Scheme 2) was similar tothe literature [31]. The simple process is as follows: amixture of benzaldehyde(20 mmol), ethyl cyanoacetate (20 mmol), hydroxypyridine anion-based PILs (2mmol), and alcohol (25 mL) wasmixed and stirredat room temperature (25-30 °C) for 20 min, then the deionized water(50 mL) was added into the mixture and solid product was graduallyprecipitated. Light yellow solid and transparent filtrates were obtainedby filtrating the mixture using sand core funnel. A white solid is obtainedafter recrystallization with 95% ethanol water solution and dryingunder vacuum at room temperature for at least 24 h. The meltingpoint of product (ethyl (E) 2 cyano 3 phenyl 2 propenoate [32]) wasmeasured by Buchi M-565, which was 49.3 °C (Lit. 47-48 °C [32, 33]).The chemical structure of the product was characterized by 1H NMR,13C NMR, and IR spectra, respectively, which was presented inSupporting Information and in good agreement with the literature[32, 33]. Moreover, the effect of the type of hydroxypyridine anionbasedPILs on catalytic performance of Knoevenagel reactionwas investigated,which was listed in Table 1 and used to correlate with thealkalinity.
96%	With molybdenum(VI) oxide In ethanol; lithium hydroxide monohydrate at 20℃; for 0.666667h; Green chemistry;	2.3. Typical Procedure for the Synthesis of 3l General procedure: 4(morpholinoethoxy)benzaldehyde (1 mmol, 0.235 g)was added to a stirring mixture of ethyl cyanoacetate(1.5 mmol, 0.170 g), and the catalytic amount of MoO3NPs (0.004 g, 3 mol%) in EtOH/H2O (4:1). It was allowedto the mixture to stir at room temperature for the timeindicated in Table II. After compilation of the reaction (thereaction progress was controlled by TLC EtOAc/n-hexane(1:1) as eluent), the reaction mixture was filtered to separateprecipitate. Next, the precipitate was dissolved in boilingethanol and filtrated to separate catalyst. In the end,formed crystalline product was filtrated to obtain the crystallinepure product.
96%	With titanium tetraethoxide In neat (no solvent) at 110℃; for 0.0833333h; Microwave irradiation; Sealed tube;	3.3. General Experimental Procedure for the Synthesis ofα,β-unsaturated Compounds under Microwave Irradiation3a-3u General procedure: A dry CEM microwave glass vial (10 mL) equipped witha magnetic stir bar was charged with aldehyde (1.1 eq), diethylmalonate/ethyl cyanoacetate (1.0 eq) and titanium ethoxide(1.1 eq). The sealed vial was subjected to microwaveirradiation at 110 °C using power 150 W for 5 minutes. Aftercooling to room temperature (rt) the reaction mixture wasdirectly charged onto a silica gel column (eluent: petroleumether/ ethyl acetate = 80:20) to provide the correspondingα,β-unsaturated compounds.
95%	With ammonium acetate; glacial acetic acid for 0.0125h; Irradiation;
95%	With ethylenediamine diacetic acid; 1-n-butyl-3-methylimidazolium tetrafluoroborate at 20℃; for 1h;
95%	With aluminum(III) oxide; potassium oxide at 26℃; for 1.5h;
95%	In N,N-dimethyl-formamide at 20℃; for 2h;
95%	In lithium hydroxide monohydrate at 30℃; for 5h;
95.2%	at 100℃; for 5h;
95%	With 3-hydroxyethylammonium-n-propanesulfonate In lithium hydroxide monohydrate at 20℃; for 0.25h;
95%	With 1,8-diazabicyclo[5.4.0]undec-7-en-8-ium acetate In lithium hydroxide monohydrate at 20℃; for 2h;
95%	With cerium trimetaphosphimate pentahydrate In ethanol at 60℃; for 2h;
95%	With potassium hydroxide at 20℃; for 3h; neat (no solvent);
95%	With 1,4-diaza-bicyclo[2.2.2]octane In lithium hydroxide monohydrate at 20℃; for 0.0166667h; Green chemistry;	Typical procedure for Knoevenagel condensation General procedure: A mixture of 1a (232 mg, 2.0 mmol) and 2a (132 mg, 2.0 mmol) in H2O (0.5 mL) and DABCO (224 mg, 2.0mmol) was stirred at room temperature for 3 min until TLC showed complete disappearance of the starting materials. The mixture was extracted by EtOAc (5 mL) and the organic layer was washed with saturated solution of NaHCO3 and brine. The organic layer was dried over Na2SO4 . Product 3aa was obtained by evaporation of the volatile portion of the organic layer and was puried by recrystallization from EtOAc/hexane mixture. Product 3aa was obtained in 80% yield (262 mg). The product was identied based on its physical and spectral characteristics. The remaining compounds 3ab-3db were synthesized in a similar manner.
95%	With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 50℃; for 0.5h; Green chemistry;
95%	With potassium fluoride-clinoptilolite In ethanol at 40℃; for 1.33333h; Sonication; Green chemistry; stereoselective reaction;	General Procedure for the Knoevenagel Condensation General procedure: In a typical experiment, equimolar amounts of benzaldehyde (212 mg, 2.0 mmol), malononitrile (2) (132 mg, 2.0 mmol), predried catalyst KF-CP [160 mg and 200 mg in the case of ethyl cyanoacetate (4)] and ethanol (2 mL) were placed into a flat bottomed glass tube and mixed thoroughlybefore irradiation. The mixture was sonicated for the specified reaction time at 40°C (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, dichloromethane (10 mL) was added to the mixture andthen filtrated. The solvent was removed under reduced pressure to afford the crude product. Further purification was performed by recrystallization in 95% ethanol to give 277mg of pure product 3a. The products were characterized by 1H NMR, mp, and all data were compared to the literature.
95%	Stage #1: benzaldehyde With C₉H₁₁ClN₂O*ClHO₄ In neat (no solvent) for 0.166667h; Stage #2: ethyl 2-cyanoacetate In neat (no solvent) at 25 - 30℃; for 0.5h;	2.3 General Procedure for the Synthesis of Acrylonitrile’s and Cyanoacrylates General procedure: In an oven dried clean 10 ml round bottom flask equipped with a magnetic stir bar, benzaldehyde (0.9mmol) and (5f) (30mol%) were taken and stirred for 10 min. Under the stirring condition, active methylene compound (0.9 mmol) was added to the reaction mixture and allowed the reaction mixture to stir at room temperature for 30 min. Upon completion of reaction (monitored by TLC), 5 ml of ethyl acetate and water was added to the reaction mixture. Two layers formed were separated by using separating funnel. The aqueous layer was washed with ethyl acetate (5ml × 3 times). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was subjected to column chromatography to obtain the corresponding product. The products were confirmed by 1H, 13C NMR and HRMS analysis.
94%	With rac-Pro-OH In dimethyl sulfoxide at 20℃; for 16h;
94%	Stage #1: ethyl 2-cyanoacetate With graphene oxide In neat (no solvent) at 20℃; for 0.5h; Stage #2: benzaldehyde In neat (no solvent) at 20℃; for 4h;	General procedure for Knoevenagel condensation reaction General procedure: The organocatalyst GO was stirred with 2 mmol of manolonitritefor 30 min at room temperature in 25 mL RB flask. To this mix-ture corresponding aldehyde (1 mmol) was added and the resultingmixture was stirred for appropriate time. After completion of thereaction, the reaction mixture was diluted with dichloromethanefollowed by subsequent separation of organic and aqueous layersby separating funnel. The organic layer was dried over Na2SO4.After removal of solvents, the crude product was purified by col-umn chromatography using EtOAc/hexane as eluent. All the yieldswere calculated from isolated products.
94%	With dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate In lithium hydroxide monohydrate at 40℃; for 2h;
94%	With silica coated nano-Fe₃O₄ supported basic ionic liquid at 70℃; for 0.25h;
93%	With 3-butyl-1-methyl-1H-imidazol-3-ium hydroxide at 25 - 30℃; for 0.2h;
93%	With acetate-intercalated NiZn mixed basic salt In lithium hydroxide monohydrate at 50℃; for 1h;
92%	With 1-methyl-piperazine at 25 - 30℃; for 0.75h;
91%	With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 24h; Ambient temperature;
91%	With C₁₀H₂₁N₂O₂⁽¹⁺⁾*CF₃O₃S^(1-) In neat (no solvent) at 20℃; for 0.5h;
91%	With KF modified clay In methanol at 20℃; for 0.133333h; Green chemistry;	General procedure for the synthesis of substitutedalkenes. General procedure: The synthesis of substituted alkenes wasrealized by introducing into a fl ask an equimolarmixture of aromatic aldehyde and malononitrile orethyl cyanoacetate in methanol by adding 20 mg of KFmodified clay as a heterogeneous catalyst. The mixture isstirred at room temperature. The condensation reactionis monitored by thin-layer chromatography (eluent =9 mL of hexane and 1 mL of ethyl acetate), the revelationis carried out using (utilizing, employing, through) a UVlamp. At the end of the reaction, the product precipitates. The latter is taken up in dichloromethane (2 × 10 mL).The fi ltrate is dried over Na2SO4 and the solvent isevaporated at reduced pressure. The product obtained ispurifi ed by recrystallization from ethanol.
90%	With piperazine for 0.0666667h; microwave irradiation;
90%	With sodium hydroxide at 20℃; for 0.5h;
90%	With OH^--modified hydrotalcite; lithium hydroxide monohydrate at 60℃; for 10h;
90%	for 0.05h; microwave irradiation;
90%	With disodium sulphide; aluminum(III) oxide In dichloromethane for 0.416667h; Heating;
90%	With 1-(2-OPPh₂-propyl)-3-methylimidazolium hexafluorophosphate at 60℃; for 0.383333h;
90%	In propylene glycol; lithium hydroxide monohydrate at 20℃; for 2h; Green chemistry;	Typical experimental procedurefor the synthesis of nitriles / acrylates / acrylamides General procedure: When3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde (1.0 mmol) andmalononitrile (1.0 mmol) were stirred in a mixture of propan-1,2-diol and water(4 mL and 2.5 mL, respectively) for 8minutes, a light yellow solid was obtained which was filtered and dried.Recrystallization from ethanol-DMF mixture afforded the pure 2-[(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene]malononitrile.Similar procedure was adopted for the synthesis of homo/heteroaryl basedacrylates and acrylamides from their corresponding aldehydes and ethyl2-cyanoacetate and 2-cyanoacetamide, respectively in 2 - 6 hours.
90%	With Quinine In neat (no solvent) at 20℃; for 0.5h; Green chemistry;
90%	With ammonia hydrochloride at 20℃; for 0.583333h;
89%	With hexamethylenetetramine In lithium hydroxide monohydrate for 0.0833333h; microwave irradiation;
89%	With calcium hydroxyapatite at 80℃; for 0.0333333h; Inert atmosphere; Microwave irradiation; Neat (no solvent);
88%	With tetrahydridotris(triphenylphosphine)ruthenium(IV) In tetrahydrofuran at 65℃; for 24h; also Ir- and Re-catalysts, other aldehydes and ketones; also reactions with malononitrile;
88%	With tetrahydridotris(triphenylphosphine)ruthenium(IV) In tetrahydrofuran at 65℃; for 24h;
88%	With potassium-exchanged zirconium hydrogen phosphate at 60℃; for 3h;
88%	With rhenium(I) pentacarbonyl bromide at 110℃; for 2h;
88%	With 1,1,3,3-tetramethylguanidinium lactate at 20℃; for 2.5h;
88%	With polyaniline In ethanol for 2h; Reflux;
88%	With 1-butyl-3-methylimidazolium-(S)-2-pyrrolidinecarboxylic acid ionic liquid In lithium hydroxide monohydrate at 25℃; for 0.666667h; stereoselective reaction;
88%	With pyridine at 95℃; for 6h;	Procedure for the synthesis of β-Cyanostyrenes 1a-m: General procedure: The mixture of aromatic aldehyde (10.0 mmol), malononitrile or ethylcyanoacetate (11.0 equiv), pyridine (10.0 mmol) was stirred at 95 oC for 6 h. The progress of reaction was monitored by using TLC. After the completion of reaction, water (10 mL) was added to the reaction mixture and extracted with dichloromethane (3 X 10 mL) and the combined organic layer was dried over anhydrous sodium sulphate and solvent was evaporated under vacuum. The crude products were purified by column chromatography using hexane as eluent and characterized as b-cyanostyrenes 1a-m.
88%	In methanol at 100℃; for 2h; Inert atmosphere;
88%	With pyridine at 95℃;	β-Cyanostyrenes 1; General Procedure General procedure: β-Cyanostyrenes were prepared according to the reported proce-dure. 18A mixture of aromatic aldehyde (10.0 mmol), malononitrile or ethylcyanoacetate (11.0 equiv), and pyridine (0.805 mL, 10.0 mmol) washeated at reflux temperature (95 C) for 6-8 h. The progress of the re-action was monitored by TLC. After the completion of reaction, H 2 O(10 mL) was added to the reaction mixture and extracted with CH 2 Cl 2(3 × 10 mL). The combined organic layers were dried (anhyd Na 2 SO 4 )and the solvent was evaporated under vacuum. Finally, the crude res-idue was purified by column chromatography using hexane as eluentand characterized as -cyanostyrene 1.
87%	With 4-dimethylaminopyridine at 80 - 85℃; for 3h;
87%	With magnesium(II) oxalate; mesoporous silica for 0.02h; Microwave irradiation; neat (no solvent);
87%	With piperidine In ethanol at 20℃; for 16h;	Ethyl (2E)-2-cyano-3-phenylprop-2-enoate- Compound BX Ethyl cyanoacetate (5.65 g, 50 mmol), benzaldehyde (5.3 g, 50 mmol) and piperidine (0.50 mL) were stirred in ethanol (15 ml) at RT for 16 h. Solid was filtered off, dissolved in methanol and the solution was concentrated to give the title compound as an oil that crystallized upon cooling (9.67 g, 87%). 1H NMR (500 MHz, Chloroform-d) δ 8.25 (s, 1 H), 8.04 - 7.93 (m, 2H), 7.55 (t, J = 7.3 Hz, 1H), 7.51 (t, J = 7.5 Hz, 2H), 4.39 (q, J = 7.1 Hz, 2H), 1.40 (t, J = 7.1 Hz, 3H).
86%	With ethylammonium nitrate at 20℃; for 8h;
86%	With controllable acid-base bifunctionalized mesoporous silica at 100℃; for 0.166667h; Microwave irradiation; Neat (no solvent);
86.8%	With zinc oxide In toluene at 79.84℃; for 6h; Inert atmosphere;
85.6%	With anhydrous zinc chloride at 100℃; for 1.5h;
85%	With tellurium tetrachloride at 80℃; for 0.916667h;
85.6%	at 100℃; for 6h;
84%	With tetra(n-butyl)ammonium hydroxide In ethanol; lithium hydroxide monohydrate for 0.0666667h; microwave irradiation;
84%	With piperidine In dichloromethane at 20℃; for 20h; Inert atmosphere;
84%	With 1,1‑(butane‑1,4‑diyl)bis(1H‑imidazole‑3‑ium) dihydrogen phosphate In ethanol; lithium hydroxide monohydrate at 80℃; for 0.433333h;	General procedure for the synthesisof arylidene malononitrile and ethyl (E)-3-(aryl)-2-cyanoacrylate derivatives General procedure: In a 25.0-mL round-bottom flask, a mixture of aromaticaldehyde (1) (1.0 mmol), malononitrile (2) or ethyl cyanoacetate(3) (1.1 mmol) and [H2-Bisim][H2PO4]2 (0.005 g,0.013 mmol) in 5.0 mL of EtOH/H2O (1:1) was stirredmagnetically at 80.0 °C for the appropriate time. The reactionprocess was monitored by TLC [n-hexane:ethyl acetate(7:3)]. After cooling of the mixture, 5.0 mL of water wasadded to it and after the stirring, the solid product was filteredand washed with cold water, dried and recrystallizedwith ethanol without needing to any extra purification step(Scheme 2).
83%	With tripotassium phosphate tribasic In ethanol at 20℃; for 1h;
83%	With piperazine-grafted reduced graphene oxide (rGO-NH) In ethanol at 60℃; for 21h;
83%	With piperidine; glacial acetic acid In toluene Inert atmosphere; Reflux;
82%	for 1h;
82%	With aluminum(III) oxide In dichloromethane at 22℃; for 0.333333h;
81%	With cellulose supported tetraethylenepantamine In ethanol for 1h; Heating;

Reference： [1]Rodriguez, Isabel; Iborra, Sara; Corma, Avelino; Rey, Fernando; Jorda, Jose L. [Chemical Communications, 1999, # 7, p. 593 - 594]
[2]Oskooie, Hossein A.; Roomizadeh, Elham; Heravi, Majid M. [Journal of Chemical Research, 2006, # 4, p. 246 - 247]
[3]Yi, Wen-Bin; Yin, Ya-Qing; Cai, Chun [Organic Preparations and Procedures International, 2007, vol. 39, # 1, p. 71 - 75]
[4]Location in patent: experimental part Trilla, Montserrat; Pleixats, Roser; Man, Michel Wong Chi; Bied, Catherine [Green Chemistry, 2009, vol. 11, # 11, p. 1815 - 1820]
[5]Rajesh Krishnan; Sree Niveditha; Sreekumar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 3, p. 428 - 431]
[6]Rasero-Almansa, Antonia M.; Corma, Avelino; Iglesias, Marta; Sánchez, Félix [ChemCatChem, 2013, vol. 5, # 10, p. 3092 - 3100]
[7]Corma; Iborra; Rodriguez; Sanchez [Journal of Catalysis, 2002, vol. 211, # 1, p. 208 - 215]
[8]Krishnan, G. Rajesh; Sreekumar, Krishnapillai [European Journal of Organic Chemistry, 2008, # 28, p. 4763 - 4768]
[9]Yi, Xiu-Chun; Huang, Meng-Xuan; Qi, Yan; Gao, En-Qing [Dalton Transactions, 2014, vol. 43, # 9, p. 3691 - 3697]
[10]Zhang, Guangcai; Zhang, Tong; Zhang, Xiongfu; Yeung, King Lun [Catalysis Communications, 2015, vol. 68, p. 93 - 96]
[11]Oka, Yuya; Kuroda, Yoshiyuki; Matsuno, Takamichi; Kamata, Keigo; Wada, Hiroaki; Shimojima, Atsushi; Kuroda, Kazuyuki [Chemistry - A European Journal, 2017, vol. 23, # 39, p. 9362 - 9368]
[12]Mori, Kohsuke; Hara, Takayoshi; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi [Journal of the American Chemical Society, 2003, vol. 125, # 38, p. 11460 - 11461]
[13]Wiles, Charlotte; Watts, Paul; Haswell, Stephen J. [Tetrahedron, 2004, vol. 60, # 38, p. 8421 - 8427]
[14]Khan, Faiz Ahmed; Dash, Jyotirmayee; Satapathy, Rashmirekha; Upadhyay, Sarasij K. [Tetrahedron Letters, 2004, vol. 45, # 15, p. 3055 - 3058]
[15]Location in patent: experimental part Ribeiro, Sonia M.; Serra, Arménio. C.; Gonsalves, A.M. D'A. Rocha [Applied Catalysis A: General, 2011, vol. 399, # 1-2, p. 126 - 133]
[16]Location in patent: experimental part Li, Guowei; Xiao, Jia; Zhang, Wenqin [Green Chemistry, 2012, vol. 14, # 8, p. 2234 - 2242]
[17]Sugahara, Kosei; Kimura, Toshihiro; Kamata, Keigo; Yamaguchi, Kazuya; Mizuno, Noritaka [Chemical Communications, 2012, vol. 48, # 67, p. 8422 - 8424]
[18]Zamani, Farzad; Rezapour, Mehdi; Kianpour, Sahar [Bulletin of the Korean Chemical Society, 2013, vol. 34, # 8, p. 2367 - 2374]
[19]Liu, Yuting; Li, Rong; Xing, Yanjun [Heterocycles, 2015, vol. 91, # 7, p. 1385 - 1397]
[20]Keithellakpam, Sanjoy; Moirangthem, Nimalini; Laitonjam, Warjeet S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 9, p. 1157 - 1161]
[21]Wang, Peng; Chen, Kai; Liu, Qing; Wang, Huai-Wei; Azam, Mohammad; Al-Resayes, Saud I.; Lu, Yi; Sun, Wei-Yin [Dalton Transactions, 2017, vol. 46, # 34, p. 11425 - 11430]
[22]Jia, Xiaoli; Zhang, Xiaoyu; Wang, Zhijun; Zhao, Sanhu [Synthetic Communications, 2022, vol. 52, # 5, p. 774 - 786]
[23]Jia, Xiaoli; Zhang, Xiaoyu; Wang, Zhijun; Zhao, Sanhu [Synthetic Communications, 2022, vol. 52, # 5, p. 774 - 786]
[24]Mitra, Alok Kumar; De, Aparna; Karchaudhuri, Nilay [Synthetic Communications, 1999, vol. 29, # 16, p. 2731 - 2739]
[25]Wiles, Charlotte; Watts, Paul; Haswell, Stephen J.; Pombo-Villar, Esteban [Tetrahedron, 2005, vol. 61, # 45, p. 10757 - 10773]
[26]Heravi, Majid M.; Tehrani, Maryam H.; Bakhtiari, Khadijeh; Oskooie, Hossein A. [Journal of Chemical Research, 2006, # 9, p. 561 - 562]
[27]Location in patent: experimental part Li, Guowei; Xiao, Jia; Zhang, Wenqin [Green Chemistry, 2011, vol. 13, # 7, p. 1828 - 1836]
[28]Chen, Chen; Yang, Hanmin; Chen, Jizhong; Zhang, Ran; Guo, Li; Gan, Huimei; Song, Baoning; Zhu, Wenwen; Hua, Li; Hou, Zhenshan [Catalysis Communications, 2014, vol. 47, p. 49 - 53]
[29]Location in patent: experimental part Xu, Da-Zhen; Liu, Yingjun; Shi, Sen; Wang, Yongmei [Green Chemistry, 2010, vol. 12, # 3, p. 514 - 517]
[30]Location in patent: experimental part Ying, An-Guo; Wu, Cheng-Lin; He, Guang-Hong [Asian Journal of Chemistry, 2012, vol. 24, # 2, p. 653 - 656]
[31]Minato, Takuo; Suzuki, Kosuke; Kamata, Keigo; Mizuno, Noritaka [Chemistry - A European Journal, 2014, vol. 20, # 20, p. 5946 - 5952]
[32]Ammar, Hafedh Belhadj; Chtourou, Manef; Frikha, Mohamed Hédi; Trabelsi, Mahmoud [Ultrasonics Sonochemistry, 2015, vol. 22, p. 559 - 564]
[33]Xu, Hao; Pan, Liyang; Fang, Xiaomin; Liu, Baoying; Zhang, Wenkai; Lu, Minghua; Xu, Yuanqing; Ding, Tao; Chang, Haibo [Tetrahedron Letters, 2017, vol. 58, # 24, p. 2360 - 2365]
[34]Tryambake, Pravin. T. [Asian Journal of Chemistry, 2017, vol. 29, # 11, p. 2401 - 2405]
[35]Xie, Bin; Xu, Yingjie; Tang, Xiaochen; Shu, Hegang; Chen, Tingting; Zhu, Xiao [Journal of Molecular Liquids, 2018, vol. 268, p. 610 - 616]
[36]Pourshojaei, Yaghoub; Eskandari, Khalil; Elhami, Elaheh; Asadipour, Ali [Journal of Nanoscience and Nanotechnology, 2019, vol. 19, # 9, p. 5965 - 5973]
[37]Ramaiah, Manjunatha M.; Shivananju, Nanjunda Swamy; Shubha, Priya Babu [Letters in Organic Chemistry, 2020, vol. 17, # 2, p. 107 - 115]
[38]Dave; Augustine [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 6, p. 403 - 405]
[39]Su, Ce; Chen, Zhen-Chu; Zheng, Qin-Guo [Synthesis, 2003, # 4, p. 555 - 559]
[40]Wang, Shu-Xiang; Li, Ji-Tai; Yang, Wen-Zhi; Yin, Ya-Hui; Xie, Zi-Hui [Synthetic Communications, 2004, vol. 34, # 5, p. 829 - 834]
[41]Kantam, M. Lakshmi; Ravindra; Reddy, Ch. Venkat; Sreedhar; Choudary [Advanced Synthesis and Catalysis, 2006, vol. 348, # 4-5, p. 569 - 578]
[42]Hara, Takayoshi; Kanai, Satoko; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7455 - 7462]
[43]Lai, Guoqiao; Peng, Jiajian; Li, Jiayun; Qiu, Huayu; Jiang, Jianxiong; Jiang, Kezhi; Shen, Yongjia [Tetrahedron Letters, 2006, vol. 47, # 39, p. 6951 - 6953]
[44]Location in patent: experimental part Fang, Dong; Fei, Zheng-Hao; Liu, Zu-Liang [Monatshefte fur Chemie, 2008, vol. 139, # 7, p. 799 - 803]
[45]Location in patent: experimental part Ying, An-Guo; Wang, Li-Min; Wang, Le-Le; Chen, Xin-Zhi; Ye, Wei-Dong [Journal of Chemical Research, 2010, # 1, p. 30 - 33]
[46]Location in patent: experimental part Yi, Jianglong; Fu, Zhiyong; Liao, Shijun; Song, Desheng; Dai, Jingcao [Journal of Materials Chemistry, 2011, vol. 21, # 17, p. 6144 - 6147]
[47]Location in patent: experimental part Wei, Yudan; Zhang, Shuguo; Yin, Shuangfeng; Zhao, Chang; Luo, Shenglian; Au, Chak-Tong [Catalysis Communications, 2011, vol. 12, # 14, p. 1333 - 1338]
[48]Abaee, Mohammad Saeed; Cheraghi, Somayeh [Turkish Journal of Chemistry, 2014, vol. 38, # 4, p. 650 - 660]
[49]Yu, Ya-Qin; Wang, Zhong-Liang [Journal of the Chinese Chemical Society, 2013, vol. 60, # 3, p. 288 - 292]
[50]Keipour, Hoda; Hosseini, Abolfazl; Khalilzadeh, Mohammad A.; Ollevier, Thierry [Letters in Organic Chemistry, 2015, vol. 12, # 9, p. 645 - 650]
[51]Burate, Pralhad A.; Javle, Balasaheb R.; Desale, Pranjal H.; Kinage, Anil K. [Catalysis Letters, 2019, vol. 149, # 9, p. 2368 - 2375]
[52]Cardillo, Giuliana; Fabbroni, Serena; Gentilucci, Luca; Gianotti, Massimo; Tolomeklli, Alessandra [Synthetic Communications, 2003, vol. 33, # 9, p. 1587 - 1594]
[53]Islam, Sk Manirul; Roy, Anupam Singha; Dey, Ram Chandra; Paul, Sumantra [Journal of Molecular Catalysis A: Chemical, 2014, vol. 394, p. 66 - 73]
[54]Ang, Wei Jie; Chng, Yong Sheng; Lam, Yulin [RSC Advances, 2015, vol. 5, # 99, p. 81415 - 81428]
[55]Zhang, Qiang; Ma, Xiao-Ming; Wei, Huai-Xin; Zhao, Xin; Luo, Jun [RSC Advances, 2017, vol. 7, # 85, p. 53861 - 53870]
[56]Ranu, Brindaban C.; Jana, Ranjan [European Journal of Organic Chemistry, 2006, # 16, p. 3767 - 3770]
[57]Hara, Takayoshi; Kurihara, Jun; Ichikuni, Nobuyuki; Shimazu, Shogo [Chemistry Letters, 2010, vol. 39, # 3, p. 304 - 305]
[58]Mukhopadhyay, Chhanda; Datta, Arup [Synthetic Communications, 2008, vol. 38, # 13, p. 2103 - 2112]
[59]Murahashi, Shun-Ichi; Naota, Takeshi; Taki, Hiroshi; Mizuno, Masahiko; Takaya, Hikaru; Komiya, Sanshiro; Mizuho, Yuji; Oyasato, Naohiko; Hiraoka, Makiko; Hirano, Masafumi; Fukuoka, Atsushi [Journal of the American Chemical Society, 1995, vol. 117, # 50, p. 12436 - 12451]
[60]Gao, Xiaochong; Gao, Can; Gao, Ruichang [Asian Journal of Chemistry, 2015, vol. 27, # 6, p. 2145 - 2148]
[61]Bentahar, S.; Dbik, A.; Khomri, M. El; Lacherai, A.; Messaoudi, N. El; Sabour, A.; Taleb, M. Ait [Russian Journal of Applied Chemistry, 2020, vol. 93, # 9, p. 1438 - 1444][Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2020, # 9]
[62]Mitra, Alok Kumar; Banerjee, Sajal Kumar; Chattopadhyay, Sarmishtha [Journal of the Indian Chemical Society, 2003, vol. 80, # 10, p. 921 - 922]
[63]Zhang, Ming; Zhang, Ai-Qin; Deng, Zhi-Hong [Journal of Chemical Research, 2005, # 1, p. 69 - 70]
[64]Ebitani, Kohki; Motokura, Ken; Mori, Kohsuke; Mizugaki, Tomoo; Kaneda, Kiyotomi [Journal of Organic Chemistry, 2006, vol. 71, # 15, p. 5440 - 5447]
[65]Yadav, Jhillu S.; Subba Reddy, Basi V.; Basak, Ashok K.; Visali, Boddapati; Narsaiah, Akkirala Venkat; Nagaiah, Kommu [European Journal of Organic Chemistry, 2004, # 3, p. 546 - 551]
[66]Heravi, Majid M.; Bakhtiari, Khadijeh; Taheri, Shima; Oskooie, Hossein A. [Journal of the Chinese Chemical Society, 2007, vol. 54, # 6, p. 1557 - 1560]
[67]Location in patent: experimental part Valizadeh, Hassan; Gholipour, Hamid [Synthetic Communications, 2010, vol. 40, # 10, p. 1477 - 1485]
[68]Jayalakshmi, Lakshmi Narayanan; Karuppasamy, Ayyanar; Stalindurai, Kesavan; Sivaramakarthikeyan, Ramar; Devadoss, Vellasamy; Ramalingan, Chennan [Tetrahedron Letters, 2015, vol. 56, # 28, p. 4207 - 4210]
[69]Jain, Kavita; Chaudhuri, Saikat; Pal, Kuntal; Das, Kalpataru [New Journal of Chemistry, 2019, vol. 43, # 3, p. 1299 - 1304]
[70]Waghmare, Smita R. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 6, p. 849 - 855]
[71]Karchgaudhuri, Nilay; De, Aparna; Mitra, Alok Kumar [Journal of Chemical Research - Part S, 2002, # 4, p. 180 - 183]
[72]Location in patent: experimental part Mallouk, Siham; Bougrin, Khalid; Laghzizil, Abdelaziz; Benhida, Rachid [Molecules, 2010, vol. 15, # 2, p. 813 - 823]
[73]Lin, Yingrui; Zhu, Xianchao; Xiang, Min [Journal of Organometallic Chemistry, 1993, vol. 448, # 1-2, p. 215 - 218]
[74]Lin, Yingrui; Zhu, Xianchao; Xiang, Min [Journal of Organometallic Chemistry, 1993, vol. 448, # 1-2, p. 215 - 218]
[75]Curini, Massimo; Epifano, Francesco; Marcotullio, Maria Carla; Rosati, Ornelio; Tsadjout, Andre [Synthetic Communications, 2002, vol. 32, # 3, p. 355 - 362]
[76]Zuo, Wei-Xiong; Hua, Ruimao; Qiu, Xianqing [Synthetic Communications, 2004, vol. 34, # 17, p. 3219 - 3225]
[77]Zhang, Jicheng; Jiang, Tao; Han, Buxing; Zhu, Anlian; Ma, Xiumin [Synthetic Communications, 2006, vol. 36, # 22, p. 3305 - 3317]
[78]Location in patent: experimental part Zhang, Ai-Qin; Zhang, Ning; Hong, Sanguo; Zhang, Ming [Synthetic Communications, 2009, vol. 39, # 17, p. 3024 - 3030]
[79]Location in patent: experimental part Song, Hongbing; Yu, Yinghao; Chen, Xuewei; Li, Xuehui; Xi, Hongxia [Cuihua Xuebao/Chinese Journal of Catalysis, 2012, vol. 33, # 4-6, p. 666 - 669]
[80]Singh, Fateh V.; Mangaonkar, Saeesh R.; Kole, Priyanka B. [Synthetic Communications, 2018, vol. 48, # 17, p. 2169 - 2176]
[81]Leo, Pedro; Orcajo, Gisela; Briones, David; Rodríguez-Diéguez, Antonio; Choquesillo-Lazarte, Duane; Calleja, Guillermo; Martínez, Fernando [Dalton Transactions, 2019, vol. 48, # 30, p. 11556 - 11564]
[82]Mangaonkar, Saeesh R.; Singh, Fateh V. [Synthesis, 2019, vol. 51, # 23, p. 4473 - 4486]
[83]Narsaiah, A. Venkat; Basak; Visali; Nagaiah [Synthetic Communications, 2004, vol. 34, # 16, p. 2893 - 2901]
[84]Location in patent: experimental part Yuan, Shizhen; Li, Zhen; Xu, Ling [Research on Chemical Intermediates, 2012, vol. 38, # 2, p. 393 - 402]
[85]Current Patent Assignee: HARVARD UNIVERSITY; EVOTEC AG - WO2016/191658, 2016, A1 Location in patent: Paragraph 00727; 00728-00729
[86]Hu, Yi; Chen, Jue; Le, Zhang-Gao; Zheng, Qin-Guo [Synthetic Communications, 2005, vol. 35, # 5, p. 739 - 744]
[87]Location in patent: experimental part Peng, Yin; Wang, Jianyao; Long, Jie; Liu, Guohua [Catalysis Communications, 2011, vol. 15, # 1, p. 10 - 14]
[88]Li, Jerry P. H; Adesina, Adesoji A; Kennedy, Eric M; Stockenhuber, Michael [Physical Chemistry Chemical Physics, 2017, vol. 19, # 39, p. 26630 - 26644]
[89]Shantan Rao; Venkataratnam [Tetrahedron Letters, 1991, vol. 32, # 41, p. 5821 - 5822]
[90]Khan, Rahat H.; Mathur, Raj K.; Ghosh, Anil C. [Synthetic Communications, 1996, vol. 26, # 4, p. 683 - 686]
[91]Liu, Yong; Peng, Jiajian; Zhai, Shangru; Li, Jiayun; Mao, Jianjiang; Li, Meijiang; Qiu, Huayu; Lai, Guoqiao [European Journal of Inorganic Chemistry, 2006, # 15, p. 2947 - 2949]
[92]Balalaie, Saeed; Bararjanian, Morteza [Synthetic Communications, 2006, vol. 36, # 4, p. 533 - 539]
[93]Vivier, Delphine; Soussia, Ismail Ben; Rodrigues, Nuno; Lolignier, Stéphane; Devilliers, Maïly; Chatelain, Franck C.; Prival, Laetitia; Chapuy, Eric; Bourdier, Geoffrey; Bennis, Khalil; Lesage, Florian; Eschalier, Alain; Busserolles, Jérôme; Ducki, Sylvie [Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 1076 - 1088]
[94]Rahmatizadeh-Pashaki, Zahra; Daneshvar, Nader; Shirini, Farhad [Journal of the Iranian Chemical Society, 2021, vol. 18, # 8, p. 2135 - 2149]
[95]Li [Journal of Chemical Research - Part S, 2000, # 11, p. 524 - 525]
[96]Rodrigo, Eduardo; García Alcubilla, Beatriz; Sainz, Raquel; Fierro, J. L. García; Ferritto, Rafael; Cid, M. Belén [Chemical Communications, 2014, vol. 50, # 47, p. 6270 - 6273]
[97]Skvorcova, Marija; Jirgensons, Aigars [Organic Letters, 2017, vol. 19, # 10, p. 2478 - 2481]
[98]Chalais, Stephane; Laszlo, Pierre; Mathy, Arthur [Tetrahedron Letters, 1985, vol. 26, # 37, p. 4453 - 4454]
[99]Bagi, Péter; Holczbauer, Tamás; Orbán, István; Rapi, Zsolt; Varga, Bertalan [European Journal of Organic Chemistry, 2022, vol. 2022, # 14]
[100]Li, Yi-Qun; Zhou, Mei-Yun; Xu, Xin-Ming [Journal of Chemical Research - Part S, 2003, # 3, p. 134 - 135]

2
[ 79-46-9 ]
[ 2169-69-9 ]
trans-1-cyano-2,2-dimethyl-1-(ethoxycarbonyl)-3-phenylcyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate In ethanol for 4h; Heating;

Reference： [1]Babler, James H.; Spina, Kenneth P. [Tetrahedron Letters, 1985, vol. 26, # 16, p. 1923 - 1926]

3
[ 2169-69-9 ]
[ 1670-14-0 ]
[ 737-54-2 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium ethanolate In ethanol for 1h; Ambient temperature;
7.1 g	With sodium In ethanol for 4h; Inert atmosphere;	6 150 ml of ethanol was added to a flask purged with nitrogen, 0.2 g of sodium (1.73 g, 75 mmol) was subdivided and added dropwise at intervals of 10 minutes. Stirring was continued for 1 hour after completion of dropwise addition. Then, benzamidine hydrochloride (7.82 g, 50 mmol) and (E) -2-cyano-3-phenylpropenoate (10.06 g, 50 mmol) were added dropwise and stirred for 4 hours. Thereafter, the sodium chloride produced by filtration was removed, and the filtrate was distilled off under reduced pressure. Then, an acetone slurry was purified to obtain 7.1 g (26 mmol) of the compound represented by the formula (O).

Reference： [1]Lorente, A.; Navio, J. L. Garcia; Vaquero, J. J.; Soto, J. L. [Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 49 - 51]
[2]Current Patent Assignee: LG CHEM CO.,LTD. - KR2016/126792, 2016, A Location in patent: Paragraph 0256-0259

4
[ 2169-69-9 ]
phenylmagnesium bromide [ No CAS ]
[ 25634-96-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(l) iodide In diethyl ether at 0℃; for 1h;

Reference： [1]Cativiela; Diaz-De-Villegas; Galvez [Tetrahedron, 1994, vol. 50, # 32, p. 9837 - 9846]

5
[ 2169-69-9 ]
[ 6731-58-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With formic acid; triethylamine; N-tosylethylenediamine In dichloromethane at 30℃; for 2h;
94%	With 3,5-diethyl 1,4-dihydropyridine-3,5-dicarboxylate In water at 100℃; for 24h; Green chemistry; chemoselective reaction;
92%	With 2-phenylthiazoline In butan-1-ol for 8h; Heating;

92%	With palladium diacetate; potassium formate In N,N-dimethyl-formamide at 45℃; for 4h;
90%	With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 16h;	Ethyl 2-cyano-3-phenylpropanoate - Compound BY Ethyl (2E)-2-cyano-3-phenylprop-2-enoate (5.0 g, 24.8 mmol) in Ethanol (100 mL) was hydrogenated at atmospheric pressure in the presence of Pd/C (125 mg, 10%) at RT for 16 h. The reaction mixture was purged with nitrogen, filtered through a pad of celite, washed with ethanol and the filtrate was concentrated to give the title compound as a pale yellow oil (5.05 g, 90%). 1H NMR (500 MHz, Chloroform-d) δ 7.40- 7.24 (m, 5H), 4.24 (q, J = 7.2 Hz, 2H), 3.72 (dd, J = 8.4, 5.8 Hz, 1H), 3.34- 3.15 (m, 2H), 1.27 (t, J = 7.1 Hz, 3H).
89%	With sodium tetrahydroborate In ethanol at 20℃; for 3h;
88%	With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 3h;
88%	With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 28 - 30℃; for 3h;
86%	With sodium tetrahydroborate; water In toluene at 100℃; for 22h;
85%	With Amberlite(R) IRA-420 formate In N,N-dimethyl-formamide at 70℃; for 10h;
84%	With D-glucose; glucose dehydrogenase CDX₉₀₁; ene reductase OPR₁ from Lycopersicon escultentum; NADPH; sodium hydroxide In aq. phosphate buffer; isopropyl alcohol at 20℃; for 41h; Enzymatic reaction;
82%	In N,N-dimethyl-formamide at 65℃; for 8h;
80%	With polysiloxane-supported 1-benzyl-1,4-dihydronicotinamide In acetonitrile at 20℃; for 5h;
80%	With sodium tetrahydroborate In ethanol at 25℃; for 6h; Inert atmosphere; chemoselective reaction;
79%	With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In ethanol
56%	With acetic acid; zinc at 100℃; for 2.5h;	Ethyl 2-cyano-3-phenylpropanoate (34) (E)-Ethyl-2-cyano-3-phenylacrylate 34a (0.80 g,3.98 mmol) and zinc powder (3.98 g, 60.8 mmol, 16.0 equiv) were dissolved in 25 mL glacial acetic acid and the solution was stirred for 2.5 h at 100 °C. The reaction mixture was filtered through a celite pad and washed with EtOAc (50 mL). The filtrate was neutralised with aq.NaHCO3 solution and the organic layer was separated,washed with brine (2 × 25 mL), dried over Na2SO4 and the solvent removed under reduced pressure to obtain the an oil which was further purified on a short silica column with a solvent mixture of 1:9 (EtOAc/hexane). Isolated yield: 0.53 g (56%, 3.98 mmol scale)
98 % Chromat.	With hydrogen In toluene at 60℃; for 1h;
	With hydrogen In toluene at 60℃; for 1h;

Reference： [1]Xue, Dong; Chen, Ying-Chun; Cui, Xin; Wang, Qi-Wei; Zhu, Jin; Deng, Jin-Gen [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3584 - 3591]
[2]He, Qi; Xu, Zhihong; Jiang, Dehong; Ai, Wensi; Shi, Ronghua; Qian, Shan; Wang, Zhouyu [RSC Advances, 2014, vol. 4, # 17, p. 8671 - 8674]
[3]Chikashita, Hidenori; Miyazaki, Makoto; Itoh, Kazuyoshi [Journal of the Chemical Society. Perkin transactions I, 1987, p. 699 - 706]
[4]Basu, Basudeb; Bhuiyan, Md. Mosharef Hossain; Jha, Satadru [Synthetic Communications, 2003, vol. 33, # 2, p. 291 - 296]
[5]Current Patent Assignee: HARVARD UNIVERSITY; EVOTEC AG - WO2016/191658, 2016, A1 Location in patent: Paragraph 00727; 00730-00731
[6]Shia, Kak-Shan; Chang, Nien-Yin; Yip, Judy; Liu, Hsing-Jang [Tetrahedron Letters, 1997, vol. 38, # 44, p. 7713 - 7716]
[7]Ranu, Brindaban C.; Samanta, Sampak [Tetrahedron Letters, 2002, vol. 43, # 41, p. 7405 - 7407]
[8]Ranu, Brindaban C.; Samanta, Sampak [Tetrahedron, 2003, vol. 59, # 40, p. 7901 - 7906]
[9]Adair, Gareth R.A.; Kapoor, Kamal K.; Scolan, Alexandre L.B.; Williams, Jonathan M.J. [Tetrahedron Letters, 2006, vol. 47, # 50, p. 8943 - 8944]
[10]Basu, Basudeb; Bhuiyan, Md. Mosharef H.; Das, Pralay; Hossain, Ismail [Tetrahedron Letters, 2003, vol. 44, # 50, p. 8931 - 8934]
[11]Reß, Tina; Hummel, Werner; Hanlon, Steven P.; Iding, Hans; Gröger, Harald [ChemCatChem, 2015, vol. 7, # 8, p. 1302 - 1311]
[12]Basu, Basudeb; Das, Sajal; Das, Pralay; Nanda, Ashish K. [Tetrahedron Letters, 2005, vol. 46, # 49, p. 8591 - 8593]
[13]Zhang, Baolian; Zhu, Xiao-Qing; Lu, Jin-Yong; He, Jiaqi; Wang, Peng G.; Cheng, Jin-Pei [Journal of Organic Chemistry, 2003, vol. 68, # 8, p. 3295 - 3298]
[14]Location in patent: experimental part Jagdale, Arun R.; Paraskar, Abhimanyu S.; Sudalai, Arumugam [Synthesis, 2009, # 4, p. 660 - 664]
[15]Garden, Simon J.; Werneck Guimaraes, Cristiano Ruch; Correa, Marilza B.; Fernandes de Oliveira, Cesar Augusto; Da Cunha Pinto, Angelo; Bicca de Alencastro, Ricardo [Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 8815 - 8822]
[16]Mallia, Carl J.; Englert, Lukas; Walter, Gary C.; Baxendale, Ian R. [Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 875 - 883]
[17]Motokura, Ken; Fujita, Noriaki; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi [Tetrahedron Letters, 2005, vol. 46, # 33, p. 5507 - 5510]
[18]Motokura, Ken; Fujita, Noriaki; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Chemistry - A European Journal, 2006, vol. 12, # 32, p. 8228 - 8239]

6
[ 2169-69-9 ]
[ 14378-06-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate In methanol; water for 0.5h; Heating;
	With lithium hydroxide In tetrahydrofuran; water at 21℃; for 1h;

Reference： [1]Babler, James H.; Spina, Kenneth P. [Tetrahedron Letters, 1983, vol. 24, # 36, p. 3835 - 3838]
[2]Liu, Xiaoguang; Flores, Aimee A.; Situ, Lisa; Gu, Wen; Ding, Hui; Christofk, Heather R.; Lowry, William E.; Jung, Michael E. [Journal of Medicinal Chemistry, 2021, vol. 64, # 4, p. 2046 - 2063]

7
[ 2169-69-9 ]
[ 1885-38-7 ]
[ 24840-05-9 ]
[ 100-52-7 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3835 - 3838

8
[ 2169-69-9 ]
(2R,3S)-2-Cyano-3-phenyl-oxirane-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hypochlorite In acetonitrile for 1.5h; Ambient temperature;

Reference： [1]Foucaud, Andre; Bakouetila, Medard [Synthesis, 1987, # 9, p. 854 - 856]

9
[ 2169-69-9 ]
[ 504-02-9 ]
[ 107752-85-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With morpholine In ethanol Heating;
83%	In ethanol for 18h; Heating / reflux;	9.9.B To a solution of 1,3-cyclohexane dione (0.56 g, 5.0 mmole) in hot ethanol (10 ml) was added ethyl trans-α-cyanocinnamate (1.0 g, 5.0 mmole) and the mixture heated at reflux for 18 h. The mixture was cooled to room temperature, filtered and washed with ethanol to provide the desired product (1.30 g, 83%) as a white powder. 1H NMR (400 MHz; CDCl3) δ 7.29-7.0 (m, 5H); 6.2 (bs, 2H); 4.72 (s, 1H); 4.09-3.96 (m, 2H); 2.64-2.48 (m, 2H); 2.40-2.26 (m, 2H); 2.06-1.88 (m, 2H); 1.14 (t, 3H, J=7.4 Hz). LC MS shows MH+ at 314.

Reference： [1]Sharanina, L. G.; Nesterov, V. N.; Klokol, G. V.; Rodinovskaya, L. A.; Shklover, V. E.; et al. [Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 6, p. 1185 - 1191][Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 6, p. 1315 - 1322]
[2]Current Patent Assignee: GILEAD SCIENCES INC - US2009/12103, 2009, A1 Location in patent: Page/Page column 31

10
[ 1187-46-8 ]
[ 100-52-7 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tri-n-butylarsine at 80℃; for 5h;

Reference： [1]Shen, Yanchang; Yang, Baozhen [Synthetic Communications, 1989, vol. 19, # 17, p. 3069 - 3076]

11
[ 2169-69-9 ]
[ 126-81-8 ]
[ 107752-93-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With morpholine In ethanol Heating;

Reference： [1]Sharanina, L. G.; Nesterov, V. N.; Klokol, G. V.; Rodinovskaya, L. A.; Shklover, V. E.; et al. [Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 6, p. 1185 - 1191][Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 6, p. 1315 - 1322]

12
[ 2169-69-9 ]
[ 598-52-7 ]
5-cyano-3-methyl-4-oxo-6-phenyl-2-thioxohexahydropyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium In ethanol at 0℃; for 48h;

Reference： [1]Lorente, Antonio; Aurrecoechea, Luis Maria [Heterocycles, 1994, vol. 38, # 5, p. 1077 - 1088]

13
[ 2169-69-9 ]
[ 124-40-3 ]
dimethylammonium 1-phenyl-2-cyano-2-ethoxycarbonylethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfur dioxide; water In ethanol at 60℃; for 3h;

Reference： [1]Bodrikov, I. V.; Bel'skii, V. K.; Krasnov, V. L.; Pigin, O. V. [Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 11.1, p. 1793 - 1801][Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 11, p. 2228 - 2238]

14
[ 2169-69-9 ]
[ 74-89-5 ]
(2S,3S)-2-Cyano-3-phenyl-3-sulfo-propionic acid ethyl ester; compound with methylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfur dioxide; water In ethanol at 60℃; for 3h;

Reference： [1]Bodrikov, I. V.; Bel'skii, V. K.; Krasnov, V. L.; Pigin, O. V. [Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 11.1, p. 1793 - 1801][Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 11, p. 2228 - 2238]

15
[ 1076-38-6 ]
[ 2169-69-9 ]
ethyl 2-amino-5-oxo-4-phenyl-4H,5H-pyrano[3,2-c][1]benzopyran-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With acetamide; zinc(II) chloride In dimethyl sulfoxide at 60℃; for 5h;	4H-Pyrano[3,2-c]coumarin Derivatives Using the Zinc Chloride/Acetamide DES; General Procedure General procedure: 4-Hydroxycoumarin 1 (0.2 mmol), aldehyde 2 (0.2 mmol), cyanoacetate3 (0.4 mmol), ZnCl2/acetamide DES (0.5 mL), and DMSO (0.5 mL)were mixed in a 10 mL test tube. The reaction mixture was stirred for5 h while warming slowly to 60 °C in an oil bath. The progress of thereaction was monitored by TLC (PE/EtOAc 2:1 v/v). After completionof the reaction, the mixture was diluted with H2O (5 mL) and extracted with EtOAc (2 × 5 mL) by shaking vigorously. The organic layer wasseparated from the aqueous layer (which included the DES). The combinedorganic phases were concentrated under reduced pressure togive the crude product, which was purified by column chromatography(PE/EtOAc 2:1 v/v) to yield the pure product.
72%	With sodium hydride In toluene for 4h; Heating;
55%	In ethanol for 8h; Heating;

48%

With morpholine In ethanol Heating;

Reference： [1]Xie, Zongbo; Li, Hongxia; Yang, Jiangnan; Zhu, Xiao; Le, Zhanggao [Synthesis, 2021, vol. 54, # 3, p. 770 - 778]
[2]Al-Mousawi, Saleh M.; Elkholy, Yehia M.; Mohammad, Mohammad A.; Elnagdi, Mohammad H. [Organic Preparations and Procedures International, 1999, vol. 31, # 3, p. 305 - 313]
[3]Yakout, E. M. A.; Ibrahim, N. M.; Ghoneim, Kh. M.; Mahran, M. R. H. [Journal of Chemical Research, Miniprint, 1999, # 11, p. 2818 - 2847]
[4]Goncharenko, M. P.; Sharanin, Yu. A. [Russian Journal of Organic Chemistry, 1993, vol. 29, # 7.2, p. 1218 - 1229][Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 7, p. 1465 - 1479]

16
[ 2169-69-9 ]
[ 89379-02-2 ]
ethyl β-tert-butyl-α-cyano-β-phenylpropionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With toluene-4-sulfonic acid; potassium iodide In dimethyl sulfoxide for 22h; Irradiation;

Reference： [1]Russell, Glen A.; Chen, Ping; Yao; Kim [Journal of the American Chemical Society, 1995, vol. 117, # 22, p. 5967 - 5972]

17
[ 2169-69-9 ]
[ 115-11-7 ]
[ 173221-15-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sulfuric acid In acetic acid at 20℃; for 6h;

Reference： [1]Brown; Brown, John M.; Guiry; Guiry, Patrick J.; Laing; Christopher; Hursthouse; Laing; Abdul Malik; Hursthouse, Michael B.; Abdul Malik [Tetrahedron, 1995, vol. 51, # 27, p. 7423 - 7434]

18
[ 538-51-2 ]
[ 105-56-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 24h; Ambient temperature;

Reference： [1]Murahashi, Shun-Ichi; Naota, Takeshi; Taki, Hiroshi; Mizuno, Masahiko; Takaya, Hikaru; Komiya, Sanshiro; Mizuho, Yuji; Oyasato, Naohiko; Hiraoka, Makiko; Hirano, Masafumi; Fukuoka, Atsushi [Journal of the American Chemical Society, 1995, vol. 117, # 50, p. 12436 - 12451]

19
[ 100-52-7 ]
[ 105-56-6 ]
[ 123-54-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 17h; Ambient temperature;

Reference： [1]Murahashi, Shun-Ichi; Naota, Takeshi; Taki, Hiroshi; Mizuno, Masahiko; Takaya, Hikaru; Komiya, Sanshiro; Mizuho, Yuji; Oyasato, Naohiko; Hiraoka, Makiko; Hirano, Masafumi; Fukuoka, Atsushi [Journal of the American Chemical Society, 1995, vol. 117, # 50, p. 12436 - 12451]

20
[ 70254-44-3 ]
[ 2169-69-9 ]
2-Amino-5-oxo-4-phenyl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In ethanol for 0.75h; Heating;
67%	With piperidine In ethanol for 2h; Heating;

Reference： [1]El-Nabi, H. A. Abd [Pharmazie, 1997, vol. 52, # 1, p. 28 - 32]
[2]Sowellim, S. Z. A.; El-Taweel, F. M. A.; Elagamey, A. A. [Egyptian Journal of Chemistry, 1995, vol. 38, # 5, p. 511 - 522]

21
[ 2169-69-9 ]
[ 24850-33-7 ]
[ 107-05-1 ]
4-cyano-4-ethoxycarbonyl-5-phenyl-1,7-octadiene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	In tetrahydrofuran for 60h; Ambient temperature;
	With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; for 13h;

Reference： [1]Nakamura; Shim; Yamamoto [Journal of the American Chemical Society, 1997, vol. 119, # 34, p. 8113 - 8114]
[2]Nakamura; Aoyagi; Shim; Yamamoto [Journal of the American Chemical Society, 2001, vol. 123, # 3, p. 372 - 377]

22
[ 501-30-4 ]
[ 2169-69-9 ]
ethyl 2-amino-6-(hydroxymethyl)-8-oxo-4-phenyl-4,8-dihydropyrano[3,2-b]pyran-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With piperidine In ethanol for 0.166667h; Heating;
36%	With piperidine In ethanol for 4h; Heating;

Reference： [1]Piao, Ming-Zhu; Imafuku, Kimiaki [Tetrahedron Letters, 1997, vol. 38, # 30, p. 5301 - 5302]
[2]Al-Mousawi, Saleh M.; Elkholy, Yehia M.; Mohammad, Mohammad A.; Elnagdi, Mohammad H. [Organic Preparations and Procedures International, 1999, vol. 31, # 3, p. 305 - 313]

23
[ 1469-70-1 ]
[ 2169-69-9 ]
2-Cyano-2-(ethoxy-phenyl-methyl)-pent-4-enoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran for 3h; Ambient temperature;

Reference： [1]Nakamura; Sekido; Ito; Yamamoto [Journal of the American Chemical Society, 1998, vol. 120, # 27, p. 6838 - 6839]

24
[ 930-22-3 ]
[ 2169-69-9 ]
2-phenyl-3-ethoxycarbonyl-3-cyano-4-vinyltetrahydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In tetrahydrofuran at 40℃; for 1h;

Reference： [1]Shim, Jae-Goo; Yamamoto, Yoshinori [Journal of Organic Chemistry, 1998, vol. 63, # 9, p. 3067 - 3071]

25
[ 2169-69-9 ]
[ 99056-41-4 ]
2-amino-5-cyano-6-oxo-4-phenyl-1-(toluene-4-sulfonylamino)-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With piperidine In ethanol at 20℃; for 24h;

Reference： [1]Elgemeie, Galal H.; Elghandour, Ahmed H. H.; Ali, Hosny A.; Abdel-Azzez, Hassan M. [Journal of Chemical Research, Miniprint, 1999, # 1, p. 141 - 150]

26
[ 2169-69-9 ]
diethyl 3,4-trans-4,5-trans-2-amino-3-cyano-4,5-diphenyl-1-cyclopentene-1,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With ammonium chloride; zinc In tetrahydrofuran at 20℃; for 8h;
	With ytterbium(III) chloride; zinc In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Wang; Zhang [Journal of Chemical Research - Part S, 1999, # 7, p. 448 - 449]
[2]Su, Weike; Yang, Bibo [Journal of Chemical Research, 2004, # 1, p. 64 - 65]

27
[ 591-87-7 ]
[ 2169-69-9 ]
[ 6731-59-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tri-n-butyl-tin hydride In tetrahydrofuran at 20℃; for 7h;

Reference： [1]Shim, Jae-Goo; Jong, Chul Park; Chan, Sik Cho; Sang, Chul Shim; Yamamoto, Yoshinori [Chemical Communications, 2002, # 8, p. 852 - 853]

28
[ 865876-51-3 ]
[ 2169-69-9 ]
(2S,3R)-3-Cyano-2-phenyl-1-(toluene-4-sulfonyl)-4,4-divinyl-pyrrolidine-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With triphenylphosphine In tetrahydrofuran at 40℃; for 2h;

Reference： [1]Knight, Julian G.; Tchabanenko, Kirill; Stoker, Paul A.; Harwood, Simon J. [Tetrahedron Letters, 2005, vol. 46, # 37, p. 6261 - 6264]

29
[ 503-87-7 ]
[ 2169-69-9 ]
[ 95474-44-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With piperidine In ethanol at 80 - 90℃;

Reference： [1]Santos; Mourao; Uchoa; Silva; Malta; Moura; Lima; Galdino; Pitta; Barbe [Heterocyclic Communications, 2005, vol. 11, # 5, p. 433 - 440]

30
[ 97-94-9 ]
[ 591-87-7 ]
[ 2169-69-9 ]
2-cyano-2-(1-phenyl-propyl)-pent-4-enoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; hexane at 40℃; for 6h;

Reference： [1]Patil, Nitin T.; Huo, Zhibao; Yamamoto, Yoshinori [Journal of Organic Chemistry, 2006, vol. 71, # 6, p. 2503 - 2506]

31
[ 2169-69-9 ]
2-cyano-4-(cis-3,4-diethyl-6-methylcyclohex-3-enyl)-3-phenylbutyric acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran at 0℃; for 1h;

Reference： [1]Liu, Yuanhong; Shen, Baojian; Kotora, Martin; Nakajima, Kiyohiko; Takahashi, Tamotsu [Journal of Organic Chemistry, 2002, vol. 67, # 20, p. 7019 - 7028]

32
[ 2169-69-9 ]
ethyl (1R*,2S*)-1-cyano-2-phenyl-1-cyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: ethyl (E)-2-cyano-3-phenyl-2-propenoate; [bis(cyclopentadienyl)zircona]cyclopentane In tetrahydrofuran Stage #2: With iodine In tetrahydrofuran at 20℃; Further stages.;

Reference： [1]Liu, Yuanhong; Shen, Baojian; Kotora, Martin; Nakajima, Kiyohiko; Takahashi, Tamotsu [Journal of Organic Chemistry, 2002, vol. 67, # 20, p. 7019 - 7028]

33
[ 2169-69-9 ]
ethyl (E)-3-phenyl-2-(2H-1,2,3,4-tetraazol-5-yl)-2-propenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium azide; zinc dibromide In water for 0.216667h; Microwave irradiation; Green chemistry;	4 4.3. General procedure for 5-substituted 1H-tetrazoles 30e33 General procedure: A mixture of sodium azide (6mmol) and malononitrile (2mmol), ethyl cyanoacetate (1mmol), benzylidene malononitrile or ethyl (2E)-2-cyano-3-phenylacrylate (1mmol) was taken in presence of ZnBr2 or glacial AcOH in water (15mL). The reaction mixture was irradiated by microwave and monitored by TLC till completion after 10min-25min (see Table 1). The product was precipitated on hot, filtered off, washed with water, and recrystallized from ethanol.
89 % Chromat.	With sodium azide; acetic acid; 1-butyl-3-methylimidazolium chloride at 170℃; for 0.5h; microwave irradiation;

Reference： [1]El Remaily, Mahmoud Abd El Aleem Ali Ali; Mohamed, Shaaban K. [Tetrahedron, 2014, vol. 70, # 2, p. 270 - 275]
[2]Schmidt, Boris; Meid, Daniela; Kieser, Daniel [Tetrahedron, 2007, vol. 63, # 2, p. 492 - 496]

34
[ 105-56-6 ]
[ 100-51-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: benzyl alcohol In toluene at 80℃; for 2h; Stage #2: ethyl 2-cyanoacetate In toluene at 80℃; for 1h;

Reference： [1]Motokura, Ken; Fujita, Noriaki; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Jitsukawa, Koichiro; Kaneda, Kiyotomi [Chemistry - A European Journal, 2006, vol. 12, # 32, p. 8228 - 8239]

35
[ 119072-55-8 ]
[ 2169-69-9 ]
[ 108-79-2 ]
<i>N</i>-<i>tert</i>-butyl-2-cyano-2-(4,6-dimethyl-pyrimidin-2-yl)-3-phenyl-succinamic acid ethyl ester [ No CAS ]

Reference： [1]Synlett,2006,p. 615 - 617

36
[ 40032-47-1 ]
[ 105-56-6 ]
[ 2169-69-9 ]
[ 774-48-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 81% 2: 6%	With piperidine In ethanol for 4h; Heating;

Reference： [1]Augustine, John Kallikat; Naik, Yanjerappa Arthoba; Mandal, Ashis Baran; Chowdappa, Nagaraja; Praveen, Vinuthan B. [Journal of Organic Chemistry, 2007, vol. 72, # 25, p. 9854 - 9856]

37
[ 2169-69-9 ]
[ 1885-38-7 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3835 - 3838

38
[ 131807-04-0 ]
[ 2169-69-9 ]
[ 131807-01-7 ]

Yield	Reaction Conditions	Operation in experiment
48%	In 5,5-dimethyl-1,3-cyclohexadiene	20 trans-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alphacyanocinnamate EXAMPLE 20 trans-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alphacyanocinnamate A mixture of 12.5 g (62.1 mmol) of trans-ethyl alphacyanocinnamate, 26.6 g (93.2 mmol) of 4-hydroxy-1-octyloxy-2,2,6,6-tetramethylpiperidine, and 100 ml of xylene is heated at reflux. Water is removed by fractional distillation. The reaction mixture is cooled to 80° C., treated with 0.3 g of lithium amide, and diluted with 50 ml of xylene. The mixture is heated at reflux for 2 hours while ethanol is removed by fractional distillation. The reaction mixture is diluted with diethyl ether (250 ml). The organic solution is washed with 1N hydrochloric acid (100 ml), saturated sodium bicarbonate solution (100 ml), and saturated sodium chloride solution (200 ml), then dried over magnesium sulfate and concentrated to a brown oil. Purification by flash chromatography affords 13.2 g (48% yield) of the title compound, a yellow, waxy solid. Anal. Calcd. for C27 H40 N2 O3: C, 73.6; H, 9.1; N, 6.4 Found: C, 73.7; H, 9.3; N, 6.2.

Reference： [1]Current Patent Assignee: BASF SE - US5021478, 1991, A

39
[ 2169-69-9 ]
[ 144-55-8 ]
3-amino-2-benzylpropionic acid ethyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In ethanol; water	R.6 (+-)-2-Benzyl-3-(1-naphthylacetamido)propionic acid REFERENCE EXAMPLE 6 (+-)-2-Benzyl-3-(1-naphthylacetamido)propionic acid A solution of 1.01 g of 2-cyano-3-phenylpropenoic acid ethyl ester and 0.7 ml of concentrated hydrochloric acid in 20 ml of ethanol was hydrogenated over 0.1 g of platinum oxide under a hydrogen atmosphere at room temperature for 5 hours. After filtration of the catalyst, the filtrate was concentrated under reduced pressure. The residue was dissolved in water, washed with benzene, and then made alkaline by adding a 5% aqueous sodium bicarbonate solution. The alkaline solution was extracted with diethyl ether, the ethereal layer was washed with water and dried over anhydrous magnesium sulfate. Hydrogen chloride gas was passed into the ethereal solution. The ethereal solution was concentrated under reduced pressure to obtain 832 mg of 3-amino-2-benzylpropionic acid ethyl ester hydrochloride as colorless crystals.

Reference： [1]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED - US4863904, 1989, A

40
3-N-pyrrolidino-3-aminoacrylic acid ethyl ester [ No CAS ]
[ 2169-69-9 ]
2-amino-6-N-pyrrolidino-4-phenyl-4,5-dihydropyridine-3,5-dicarboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium ethanolate In ethanol	1 EXAMPLE 1 STR10 EXAMPLE 1 STR10 After boiling a solution of 20.1 g of benzylidenecyanoacetic acid ethyl ester, 18.4 g of 3-N-pyrrolidino-3-aminoacrylic acid ethyl ester and 1 g of sodium ethylate in 200 ml of ethanol for 4 hours, concentrating the solution and twice crystallizing the residue from ethanol, 2-amino-6-N-pyrrolidino-4-phenyl-4,5-dihydropyridine-3,5-dicarboxylic acid ethyl ester of melting point 122° C was obtained. Yield, 59% of theory.

Reference： [1]Current Patent Assignee: BAYER AG - US4004014, 1977, A

41
[ 2169-69-9 ]
[ 91564-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In ethanol	40 Preparation 40 To a solution of ethyl (2E) -2-cyano-3-phenylacrylate (1.2 g) in ethanol (30 iriL) was added 10% Palladium hydroxide (0.3 g) and the mixture was hydrogenated at 3 atms. for 2 hours. After removing the catalysts by filtration on celite pad, the filtarate was evaporated in vacuo. The residue was disolved in IN HCl (2mL) and washed with chloroform. The separated aqueous layer was adjusted to pH=7 by addition of saturated sodium bicarbonate solution and extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to afford ethyl 3-amino- 2-benzylpropanoate (388 mg) .IH-NMR (DMSO-d6) : δl.06 (3H, t, J = 7.2 Hz), 2.56 - 2.89 (5H, m) , 2.95 - 3.65 (2H, br) , 3.98 (2H, q, J = 7.2 Hz), 7.07 - 7.33 (5H, m) MS (ESI, m/z) : 208 (M+H)

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - WO2007/26920, 2007, A2 Location in patent: Page/Page column 33

42
[ 865876-51-3 ]
[ 2169-69-9 ]
1-(p-toluenesulfonyl)-3-cyano-3-ethoxycarbonyl-2-phenyl-5,5-divinylpyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetra-(n-butyl)ammonium iodide; triphenylphosphine In tetrahydrofuran at 40℃; for 18h;

Reference： [1]Knight, Julian G.; Stoker, Paul A.; Tchabanenko, Kirill; Harwood, Simon J.; Lawrie, Kenneth W.M. [Tetrahedron, 2008, vol. 64, # 17, p. 3744 - 3750]

43
[ 2169-69-9 ]
[ 58379-80-9 ]
[ 934291-81-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With sodium ethanolate In ethanol; dichloromethane	6.5 5. Synthesis of XO-B440; XO-B435 was prepared by methylation of tosylmethyl isocyanide (quantitative yield), and then, XO-B437 was synthesized by reaction to form a pyrrole (71% yield). Subsequently, an end objective XO-B440 was prepared by coupling with methyl 4-fluorobenzoate and hydrolysis of the ester of the resultant XO-B439 (42% yields over 2 steps, the following scheme).

Reference： [1]Current Patent Assignee: KISSEI PHARMACEUTICAL COMPANY LIMITED - EP1932833, 2008, A1 Location in patent: Page/Page column 33

44
[ 24424-99-5 ]
[ 2169-69-9 ]
[ 26250-90-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: di-<i>tert</i>-butyl dicarbonate; ethyl (E)-2-cyano-3-phenyl-2-propenoate With hydrogen In methanol for 20h; Stage #2: With methanol; sodium hydroxide at 20℃; for 2h; Stage #3: With hydrogenchloride; water In methanol	5.1.47.C C. 3-[(tert-Butoxy)carbonylamino]-2-benzylpropanoic acid. Ethyl trans-α-cyanocinnamate (2 g, 10 mmol), di-tert-butyl dicarbonate (2.6 g, 12 mmol), Raney Nickel (1 mL slurry), and MeOH (20 mL) were added together and shaken in a Parr hydrogenator under 40 psi of H2 for 20 hours. The catalyst was filter off through celite and rinsed with MeOH. The filtrate was added with NaOH (4 g, 100 mmol) and then stirred for 2 hours at room temperature to give the acid. The solvent was removed in vacuo to give an oil. The oil was diluted with water (100 mL) and then neutralized with 1N HCl. The aq. solution was extracted with EtOAc. The organic layer was subsequently washed with brine, dried over Na2SO4, filtered, and solvent removed under reduced pressure to give the acid as an oil, (2 g, 66%). MS (ESI) m/z 280.3 [M+1]+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2008/242694, 2008, A1 Location in patent: Page/Page column 56

45
[ 2169-69-9 ]
[ 2945-03-1 ]
ethyl (4RS,5RS)-1-benzyl-4-cyano-5-phenyl-pyrrolidin-2-one-4-carboxylate [ No CAS ]
ethyl (4SR,5RS)-1-benzyl-4-cyano-5-phenyl-pyrrolidin-2-one-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium hydride In tetrahydrofuran at 0 - 20℃;

Reference： [1]Comesse, Sebastien; Sanselme, Morgane; Daich, Adam [Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5566 - 5569]

46
[ 79-46-9 ]
[ 2169-69-9 ]
[ 95713-50-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In ethanol Inert atmosphere; Reflux;
64%	With potassium carbonate In ethanol at 50℃; for 22h; Heating / reflux;	1.2 Step 2 1-Cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid ethyl ester A mixture of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester (83.6 g, 415 mmol), 2-nitropropane (37 g, 415 mmol) and potassium carbonate (57.4 g, 415 mmol) in EtOH (325 mL) was heated at reflux for 4 hours, then heated to 50° C. for 18 hours. The reaction mixture was then poured into an aqueous solution of NaCl (15%, 2 L) and extracted with DCM. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified by distillation under vacuum to give 1-cyano-2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid ethyl ester (64.26 g, 64% yield, pale yellow oil) which distilled at 118° C. (oil bath temperature 157° C.).

Reference： [1]Skvorcova, Marija; Jirgensons, Aigars [Organic Letters, 2017, vol. 19, # 10, p. 2478 - 2481]
[2]Current Patent Assignee: ROCHE HOLDING AG - US2009/93525, 2009, A1 Location in patent: Page/Page column 30

47
[ 2169-69-9 ]
[ 2601-10-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium tetrahydroborate; cobalt(II) chloride hexahydrate In ethanol at 25℃; for 6h; Inert atmosphere; chemoselective reaction;

Reference： [1]Location in patent: experimental part Jagdale, Arun R.; Paraskar, Abhimanyu S.; Sudalai, Arumugam [Synthesis, 2009, # 4, p. 660 - 664]

48
[ 100-52-7 ]
[ 105-56-6 ]
[ 2169-69-9 ]
3,5-dicyano-4,6-diphenyl-5-ethoxycarbonyl-2-piperidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 58% 2: 15%	With ammonium acetate In methanol at 20℃; for 0.0833333h;

Reference： [1]Location in patent: experimental part Chakrabarty, Manas; Karmakar, Sulakshana; Arima, Shiho; Harigaya, Yoshihiro [Heterocycles, 2007, vol. 73, # C, p. 795 - 804]

49
[ 874-83-9 ]
[ 2169-69-9 ]
[ 1195190-73-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

50
[ 874-83-9 ]
[ 2169-69-9 ]
[ 1195190-97-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With ent-9-amino(9-deoxy)epi-hydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

51
[ 3160-40-5 ]
[ 2169-69-9 ]
[ 1195190-75-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

52
[ 3160-40-5 ]
[ 2169-69-9 ]
[ 1195190-99-8 ]

Yield	Reaction Conditions	Operation in experiment
66%	With ent-9-amino(9-deoxy)epi-hydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

53
[ 937-68-8 ]
[ 2169-69-9 ]
[ 1195190-82-9 ]
ethyl (1R,2R,3R,6R)-1-cyano-3-methyl-4-oxo-2-phenyl-6-(thiophen-2-yl)cyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

54
[ 937-68-8 ]
[ 2169-69-9 ]
ethyl (1S,2S,3S,6S)-1-cyano-3-methyl-4-oxo-2-phenyl-6-(thiophen-2-yl)cyclohexanecarboxylate [ No CAS ]
[ 1195191-00-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	With ent-9-amino(9-deoxy)epi-hydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

55
[ 6742-53-6 ]
[ 2169-69-9 ]
[ 1195190-74-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

56
[ 6742-53-6 ]
[ 2169-69-9 ]
[ 1195190-98-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With ent-9-amino(9-deoxy)epi-hydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

57
[ 3152-68-9 ]
[ 2169-69-9 ]
[ 1195190-81-8 ]
ethyl (1S,2R,3R,6S)-1-cyano-3-methyl-4-oxo-2,6-diphenylcyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

58
[ 2169-69-9 ]
[ 51220-06-5 ]
[ 1195190-78-3 ]

Yield	Reaction Conditions	Operation in experiment
67%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

59
[ 2169-69-9 ]
[ 1896-62-4 ]
[ 1195790-88-5 ]
ethyl (2S,6R)-1-cyano-4-oxo-2,6-diphenylcyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 9-amino-9-deoxy-epihydroquinine; o-fluoro-benzoic acid In toluene at 40℃; for 48h; optical yield given as %de; enantioselective reaction;

Reference： [1]Wu, Li-Yuan; Bencivenni, Giorgio; Mancinelli, Michele; Mazzanti, Andrea; Bartoli, Giuseppe; Melchiorre, Paolo [Angewandte Chemie - International Edition, 2009, vol. 48, # 39, p. 7196 - 7199][Angewandte Chemie, 2009, vol. 121, # 39, p. 7332 - 7335]

60
[ 931-97-5 ]
[ 2216-94-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With diphenyl(methyl)phosphine In toluene at 110℃; for 7h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Siby, Acetou; Loreau, Olivier; Taran, Frederic [Synthesis, 2009, # 14, p. 2365 - 2370]

61
[ 4476-02-2 ]
[ 2216-94-6 ]
[ 2169-69-9 ]
C₁₅H₁₇NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 74% 2: 17%	With diphenyl(methyl)phosphine In toluene at 110℃; for 4h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Siby, Acetou; Loreau, Olivier; Taran, Frederic [Synthesis, 2009, # 14, p. 2365 - 2370]

62
[ 53313-96-5 ]
[ 2216-94-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With diphenyl(methyl)phosphine In toluene at 110℃; for 5h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Siby, Acetou; Loreau, Olivier; Taran, Frederic [Synthesis, 2009, # 14, p. 2365 - 2370]

63
[ 75-86-5 ]
[ 2216-94-6 ]
[ 2169-69-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With diphenyl(methyl)phosphine In toluene at 110℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Siby, Acetou; Loreau, Olivier; Taran, Frederic [Synthesis, 2009, # 14, p. 2365 - 2370]

64
[ 2169-69-9 ]
[ 126-81-8 ]
(+)-2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester [ No CAS ]
(-)-2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: dimedone With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In toluene at 0℃; for 0.25h; Stage #2: ethyl (E)-2-cyano-3-phenyl-2-propenoate In toluene at 0℃; for 4.5h; optical yield given as %ee; enantioselective reaction;	Typical Experimental Procedure for the Enantioselective Tandem Reaction General procedure: A solution of 5,5-dimethylcyclohexane-1,2-dione (13, 35.3 mg, 0.10 mmol) and catalyst 7 (5.94 mg. 0.0010 mmol, 10 mol %) in toluene (1.0 mL) was stirred at 0 °C for 15 minutes. To this solution was added alkyl (E)-2-cyano-3-phenylacrylate (14, 0.12 mmol) and the mixture was stirred at 0 °C until the reaction was completed (TLC monitoring). The solvent was then removed under reduced pressure and the residue was purified by silica gel chromatography to afford the product 15.
	With N-[3,5-bis(trifluoromethyl)phenyl]-N'-[(9R)-6'-methoxycinchonan-9-yl]thiourea In toluene at 20℃; for 1h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Ramireddy, Naresh; Abbaraju, Santhi; Zhao, Cong-Gui [Tetrahedron Letters, 2011, vol. 52, # 50, p. 6792 - 6795]
[2]Ramireddy, Naresh; Abbaraju, Santhi; Zhao, Cong-Gui [Tetrahedron Letters, 2011, vol. 52, # 50, p. 6792 - 6795]

65
[ 865714-07-4 ]
[ 2169-69-9 ]
[ 1372800-66-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: ethyl (E)-2-cyano-3-phenyl-2-propenoate With N-((2S,3S)-1-(diphenylphosphino)-3-methylpentan-2-yl)-3,5-difluorobenzamide In 1,2-dichloro-ethane at -18℃; for 0.166667h; Stage #2: 2-vinylidenesuccinic acid diethyl ester In 1,2-dichloro-ethane at -18℃; for 4h; optical yield given as %ee; enantioselective reaction;

Reference： [1]Xiao, Hua; Chai, Zhuo; Cao, Dongdong; Wang, Hongyu; Chen, Jinghao; Zhao, Gang [Organic and Biomolecular Chemistry, 2012, vol. 10, # 16, p. 3195 - 3201]

66
[ 2169-69-9 ]
[ 26577-57-1 ]
C₂₃H₂₆N₂O₃ [ No CAS ]