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Chemical Structure| 107969-78-8
Chemical Structure| 107969-78-8
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Product Details of [ 107969-78-8 ]

CAS No. :107969-78-8 MDL No. :MFCD28963029
Formula : C11H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 190.20 Pubchem ID :-
Synonyms :

Safety of [ 107969-78-8 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 107969-78-8 ]

* 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 [ 107969-78-8 ]

[ 107969-78-8 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 2145-27-9 ]
  • [ 107969-78-8 ]
  • 8-fluoro-2-hydroxy-5-oxo-4-phenyl-3,4-dihydro-2<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromene-2-carboxylic acid methyl ester [ No CAS ]
  • 8-fluoro-2-hydroxy-5-oxo-4-phenyl-3,4-dihydro-2<i>H</i>,5<i>H</i>-pyrano[3,2-<i>c</i>]chromene-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2'-isopropylidenebis<(4S)-4-tert-butyl-4,5-dihydrooxazole>; copper(II) bis(trifluoromethanesulfonate) In diethyl ether Title compound not separated from byproducts;
  • 2
  • [ 67-56-1 ]
  • [ 100-52-7 ]
  • [ 127-17-3 ]
  • [ 107969-78-8 ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: benzaldehyde; 2-oxo-propionic acid With potassium hydroxide In methanol at 30℃; for 1h; Stage #2: methanol With acetyl chloride Heating;
22% Stage #1: benzaldehyde; 2-oxo-propionic acid With potassium hydroxide In methanol at 0 - 40℃; for 1h; Stage #2: methanol With acetyl chloride at 0 - 20℃; Reflux; 4.5.7. Methyl (E)-2-oxo-4-phenylbut-3-enoate (2j) A solution of KOH (842 mg, 15.0 mmol, 1.50 equiv) in MeOH (3 mL) was added dropwise over 30 min to a solution of pyruvic acid (0.695 mL, 10.0 mmol, 1.00 equiv) and benzaldehyde (1.02 mL,10.0 mmol, 1.00 equiv) in MeOH (0.8 mL) at 0 °C. The reaction was then stirred at 40 °C for 1 h before being cooled to 0 °C and stirred overnight. The resulting precipitate was filtered, washed with MeOH ( 2) and Et2O, and dried in vacuo. This solid (1.29 g) was then added to a solution of acetyl chloride (4.94 mL, 69.5 mmol,11.5 equiv) in MeOH (34.5 mL) at 0 °C and the reaction stirred for 30 min before being warmed to room temperature and stirred for a further 2 h. The reaction was then stirred at reflux overnight. The reaction was cooled to room temperature and directly concentrated in vacuo. The residue was dissolved in water and extracted with CH2Cl2. The organic layer was washed with NaHCO3 (sat., aq.), H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo before being purified by flash column chromatography (SiO2,pentane:EtOAc, 9:1) to afford the title compound as a yellow solid (435 mg, 22%). Data were consistent with those previously reported[26]. M.P.: 66-69 °C (CHCl3). Rf: 0.21 (pentane:EtOAc, 9:1). 1H NMR(400 MHz, CDCl3): d 7.88 (d, J 16.1 Hz, 1H), 7.68-7.60 (m, 2H),7.49-7.40 (m, 3H), 7.37 (d, J 16.1 Hz, 1H) and 3.94 ppm (s, 3H). 13CNMR (101 MHz, CDCl3): d 182.5, 162.7, 148.8, 134.1, 131.8, 129.2(2C), 129.2 (2C), 120.6 and 53.2 ppm.
Stage #1: benzaldehyde; 2-oxo-propionic acid With potassium hydroxide Stage #2: methanol Further stages.;
Stage #1: benzaldehyde; 2-oxo-propionic acid With potassium hydroxide Stage #2: methanol
Stage #1: benzaldehyde; 2-oxo-propionic acid With potassium hydroxide Stage #2: methanol

  • 3
  • [ 4640-67-9 ]
  • [ 107969-78-8 ]
  • [ 1217974-60-1 ]
  • 4
  • [ 4640-67-9 ]
  • [ 107969-78-8 ]
  • (+/-)-(2S,4R)-methyl-5-cyano-6-(4-fluorophenyl)-2-hydroxy-4-phenyl-3,4-dihydro-2H-pyran-2-carboxylate [ No CAS ]
  • 5
  • [ 107969-78-8 ]
  • [ 4592-94-3 ]
  • [ 1217974-61-2 ]
  • 6
  • [ 15799-79-8 ]
  • [ 107969-78-8 ]
  • [ 1227202-83-6 ]
  • [ 1227202-90-5 ]
  • 7
  • [ 15799-79-8 ]
  • [ 107969-78-8 ]
  • (+)-methyl 4-(4-dimethylamino-2-methoxyphenyl)-2-oxo-4-phenylbutanoate [ No CAS ]
  • 8
  • [ 107969-78-8 ]
  • [ 30182-67-3 ]
  • [ 1234199-84-8 ]
YieldReaction ConditionsOperation in experiment
98% With C29H29F6N3OS In diethyl ether at 20℃; for 5h; optical yield given as %ee; enantioselective reaction;
  • 9
  • [ 107969-78-8 ]
  • [ 1680-73-5 ]
  • C18H19ClO4 [ No CAS ]
  • 10
  • [ 107969-78-8 ]
  • [ 1680-73-5 ]
  • 7-chloro-1-oxo-5-phenyl-2-oxaspiro[5.5]undeca-3,7-diene-3-carboxylic acid methyl ester [ No CAS ]
  • 11
  • [ 546-68-9 ]
  • [ 1794-45-2 ]
  • [ 107969-78-8 ]
  • diisopropyl 3-(2-chlorophenyl)-1-hydroxy-4-phenylcyclopentane-1,2-dicarboxylate [ No CAS ]
  • [ 1277097-83-2 ]
  • 12
  • [ 546-68-9 ]
  • [ 1794-45-2 ]
  • [ 107969-78-8 ]
  • diisopropyl 3-(2-chlorophenyl)-1-hydroxy-4-phenylcyclopentane-1,2-dicarboxylate [ No CAS ]
  • 13
  • [ 107969-78-8 ]
  • [ 25163-98-8 ]
  • [ 1309576-41-7 ]
  • (4S,5R)-methyl 5-benzamido-5-isobutyl-6-oxo-4-phenyl-5,6-dihydro-4H-pyran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With C30H30N2O2; In diethyl ether; at 20℃; for 8h; General procedure: A mixture of 4-methyl-2-phenyloxazol-5(4H)-one (0.11 mmol) (1a), (E)-methyl-2-oxo-4-phenylbut-3-enoate (2a), and catalyst 4m (9 mg, 0.02 mmol) in 1.0 mL of ethyl ether was stirred at room temperature for 3 h until the disappearance of 2a (monitored by TLC). The reaction mixture was then concentrated, and the residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=1/10) to give the desired product 3a.4.2.1.
  • 14
  • [ 367-57-7 ]
  • [ 107969-78-8 ]
  • [ 1313416-54-4 ]
YieldReaction ConditionsOperation in experiment
77% With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea In dichloromethane at 20℃; for 24h; optical yield given as %ee; enantioselective reaction; 4.2. Typical procedure for asymmetric conjugate addition of ethyl 4,4,4-trifluoroacetoacetate to β,γ-unsaturated α-keto esters General procedure: A solution of (E)-methyl 2-oxo-4-phenylbut-3-enoate 1a (0.12 mmol), ethyl 4,4,4-trifluoroacetoacetate 2a (0.1 mmol), and 4d (0.01 mmol) in CH2Cl2 (0.5 mL) was stirred at room temperature for 14 h. After the solvent was evaporated under vacuum, the residue was purified by flash column chromatography over silica gel to afford 3a as a colorless oil.
  • 15
  • [ 22539-93-1 ]
  • [ 107969-78-8 ]
  • (2R,3S)-methyl 3-(benzyloxy)-2-hydroxy-4-oxo-2-styrylpentanoate [ No CAS ]
  • (2R,3R)-methyl 3-(benzyloxy)-2-hydroxy-4-oxo-2-styrylpentanoate [ No CAS ]
  • (2S,3S)-methyl 3-(benzyloxy)-2-hydroxy-4-oxo-2-styrylpentanoate [ No CAS ]
  • (2S,3R)-methyl 3-(benzyloxy)-2-hydroxy-4-oxo-2-styrylpentanoate [ No CAS ]
  • 16
  • [ 2483-57-0 ]
  • [ 107969-78-8 ]
  • 1,6-dimethyl 2-nitro-5-oxo-3-phenylhexanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea; In 1,2-dichloro-ethane; at -20℃; for 24h; General procedure: Prepared according to the general procedure Section 4.2 as a colorless oil (55.7 mg, 90% yield), a mixture of two inseparable diastereoisomers. 1H NMR (400 MHz, CDCl3) delta 7.37-7.28 (m, 8H), 7.26 (d, J=1.6 Hz, 2H), 5.49 (d, J=9.9 Hz, 1H), 5.43 (d, J=8.6 Hz, 1H), 4.33 (ddd, J=12.5, 9.6, 6.1 Hz, 2H), 3.84 (s, 3H), 3.84 (s, 3H), 3.83 (s, 3H), 3.71-3.60 (m, 4H), 3.49-3.42 (m, 2H), 3.35 (dd, J=18.7, 4.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 190.2, 190.2, 163.9, 163.3, 160.6, 160.5, 137.0, 136.1, 129.1, 129.1, 128.4, 128.4, 128.3, 128.0, 91.0, 90.9, 53.8, 53.5, 53.2, 53.1, 41.6, 41.2, 41.0, 41.0; IR (thin film) nu/cm-1: 2957, 2924, 2853, 1757, 1732, 1595, 1553, 1172, 1052, 940, 861, 549, 521; HRMS (ESI) calcd for C14H15NO7 (M-H)-: 308.0776, found: 308.0779; [alpha]D20+35.6 (c 1.0, CH2Cl2). The enantiomeric excess was determined by HPLC with a Chiralpak AD-H column (hexane/i-PrOH=90:10, lambda=208 nm, 0.8 mL/min), tmajor=21.0 min, tminor=23.0 min, 84% ee; tmajor=26.7 min, tminor=29.0 min, 79% ee.
  • 18
  • [ 21667-62-9 ]
  • [ 107969-78-8 ]
  • [ 1435943-35-3 ]
  • 19
  • [ 70591-86-5 ]
  • [ 107969-78-8 ]
  • [ 1435943-36-4 ]
  • 20
  • [ 21667-60-7 ]
  • [ 107969-78-8 ]
  • [ 1435943-37-5 ]
YieldReaction ConditionsOperation in experiment
88% With C36H50N4O4; 4-(1,1-dimethylethyl)benzoic acid In tert-butyl methyl ether at -30℃; for 120h; Molecular sieve; Inert atmosphere;
  • 21
  • [ 53882-81-8 ]
  • [ 107969-78-8 ]
  • [ 1435943-38-6 ]
YieldReaction ConditionsOperation in experiment
92% With C36H50N4O4; 4-(1,1-dimethylethyl)benzoic acid In tert-butyl methyl ether at -30℃; for 72h; Molecular sieve; Inert atmosphere;
  • 22
  • [ 107969-78-8 ]
  • [ 7391-28-8 ]
  • [ 1435943-39-7 ]
YieldReaction ConditionsOperation in experiment
87% With C36H50N4O4; 4-(1,1-dimethylethyl)benzoic acid In tert-butyl methyl ether at -30℃; for 72h; Molecular sieve; Inert atmosphere;
  • 23
  • [ 4640-67-9 ]
  • [ 107969-78-8 ]
  • [ 1435943-40-0 ]
  • 24
  • [ 107969-78-8 ]
  • [ 4592-94-3 ]
  • [ 1435943-42-2 ]
  • 25
  • [ 10075-49-7 ]
  • [ 107969-78-8 ]
  • (R)-methyl 4-(5-bromo-1,3-dimethyl-1H-indol-2-yl)-2-oxo-4-phenylbutanoate [ No CAS ]
  • 26
  • [ 10075-49-7 ]
  • [ 107969-78-8 ]
  • (R,E)-methyl 4-(5-bromo-1,3-dimethyl-1H-indol-2-yl)-2-(hydroxyimino)-4-phenylbutanoate [ No CAS ]
  • 27
  • [ 10602-08-1 ]
  • [ 107969-78-8 ]
  • methyl 4'-phenyl-3',4'-dihydro-3H-spiro[isobenzofuran-1,2'-pyran]-6'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); yttrium(III) trifluoromethanesulfonate In acetonitrile at 20℃; for 1h;
  • 28
  • [ 17898-21-4 ]
  • [ 107969-78-8 ]
  • C15H18O3 [ No CAS ]
  • [ 1620650-74-9 ]
  • (2R,4S)-methyl 4-phenyl-2-(triethylsilylmethyl)-3,4-dihydro-2H-pyran-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 98 % ee 2: 99% ee With copper(II) bis[bis((trifluoromethyl)sulfonyl)amide]; 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole at 20℃; for 17h; Inert atmosphere; enantioselective reaction;
  • 29
  • [ 107969-78-8 ]
  • [ 74288-40-7 ]
  • [ 1621104-11-7 ]
  • [ 1621102-79-1 ]
YieldReaction ConditionsOperation in experiment
With L-proline; In dimethyl sulfoxide; at 20℃; for 31h; General procedure: To a stirred solution of compound 1 (0.574mmol) and catalyst (0.115mmol) in DMSO (0.5mL) at room temperature, was added a Michael acceptor (2.0equiv). The mixture was stirred at ambient temperature for 24h while being monitored by TLC. The reaction mixture was then quenched by adding water (5mL) and the aqueous layer was extracted three times with DCM (30mL). The combined organic layers were dried over MgSO4, which was subsequently removed by filtration. The concentrated extract was subjected to silica gel for purification to afford the desired. The crude product was purified by column chromatography (EtOAc/hexane, 60:40; Rf=0.2) to afford the product (189mg, 60%) as a semi-solid [alpha]D20=+40.1 (c 0.1, CHCl3) 1H NMR (400MHz, CDCl3): delta 8.23 (d, J=8.36Hz, 2H), 7.48 (d, J=8.40Hz, 2H), 7.23 (m, 5H), 5.17 (dd, J=12.88, 12.88Hz, 2H), 4.29 (M, 1H), 4.20 (dd, J=4.01, 4.01Hz, 1H), 3.78 (s, 3H), 3.61 (m, 2H), 3.40 (m, 1H), 3.12 (dd, J=2.51, 2.50Hz, 1H), 2.42 (dd, J=8.79, 8.76Hz, 1H), 2.21 (dd, J=6.82, 6.79Hz, 1H), 1.30 (d, J=6.12Hz, 3H) ppm. 13C NMR (100MHz CDCl3): delta 208.4, 191.5, 171.2, 165.6, 161.0, 148.4, 141.7, 136.4, 130.0, 128.9, 128.6, 128.0, 123.9, 76.4, 67.4, 67.1, 64.7, 53.0, 50.7, 41.5, 40.6, 21.6ppm. HRMS (ESI+) m/z calcd for C27H26N2O10: 538.1587; found [M+H] 539.1694.
  • 30
  • [ 10493-98-8 ]
  • [ 107969-78-8 ]
  • methyl (2R,4S)-2-hydroxy-7-oxo-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In dichloromethane; at 20℃; for 0.25h; General procedure: 2-Hydroxycyclopent-2-enone (1; 23.5 mg, 0.24 mmol), keto ester 2a(38.0 mg, 0.2 mmol), and the organocatalyst 4c (4.1 mg, 0.01 mmol)were dissolved in CH2Cl2 (0.7 mL). The mixture was stirred at r.t. untilcompletion of the reaction (TLC monitoring, eluent: CH2Cl2-EtOAc,25:1). The mixture was purified by column chromatography (CH2Cl2-EtOAc, 25:1) to afford 3a-Me as a white solid; yield: 51 mg (89%); mp124-126 C; [alpha]D25 +152.4 (c 0.05, MeOH); 96% ee [deteremined byHPLC: Chiralpak AS-H; hexane-i-PrOH (9:1), 1 mL/min, 254 nm;tR (major) = 37.7 min, tR (minor) = 62.7 min].IR (KBr): 3244, 2981, 1753, 1696, 1646, 1455, 1288, 1140, 1113, 1016,703 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.41-7.20 (m, 5 H), 4.83 (s, 1 H), 3.98(ddm, J = 11.9, 6.8 Hz, 1 H), 3.86 (s, 3 H), 2.42-2.24 (m, 6 H).13C NMR (101 MHz, CDCl3): delta = 200.7, 169.3, 148.4, 148.2, 139.5,129.1, 128.2, 127.6, 95.6, 53.6, 38.4, 36.1, 32.8, 23.3.HRMS (ESI): m/z [M + H]+ calcd for [C16H16O5]+: 289.1071; found:289.1071.
  • 31
  • [ 7150-72-3 ]
  • [ 107969-78-8 ]
  • methyl (2R,4R)-2-((tert-butoxycarbonyl)amino)-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate [ No CAS ]
  • 32
  • [ 107969-78-8 ]
  • [ 154230-29-2 ]
  • methyl (S,E)-4-(4-chlorophenyl)-2-hydroxy-2-((E)-styryl)but-3-enoate [ No CAS ]
  • 33
  • [ 107969-78-8 ]
  • [ 89414-50-6 ]
  • C21H20O5 [ No CAS ]
  • 34
  • [ 107969-78-8 ]
  • [ 89414-50-6 ]
  • C21H20O5 [ No CAS ]
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