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Chemical Structure| 19955-99-8

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Product Details of [ 19955-99-8 ]

CAS No. :19955-99-8
Formula : C9H8O
M.W : 132.16
SMILES Code : O=CC1=CC=CC(C=C)=C1
MDL No. :MFCD02093761
InChI Key :CATOVPRCMWIZLR-UHFFFAOYSA-N
Pubchem ID :39390

Safety of [ 19955-99-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 19955-99-8 ]

* 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 [ 19955-99-8 ]

[ 19955-99-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 19955-99-8 ]
  • [ 107-21-1 ]
  • [ 115104-31-9 ]
  • 2
  • [ 3132-99-8 ]
  • [ 74-85-1 ]
  • [ 19955-99-8 ]
  • 3
  • [ 19955-99-8 ]
  • poly[1-(3-formylphenyl)ethylene], Mn: SEC (RI)= 12600, SEC (UV)= 11800, PD: SEC (RI)= 3.42, SEC (UV)= 3.45; monomer(s): 3-vinylbenzaldehyde [ No CAS ]
  • 4
  • [ 19955-99-8 ]
  • [ 141-97-9 ]
  • [ 57-13-6 ]
  • 6-methyl-2-oxo-4-(3-vinyl-phenyl)-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid ethyl ester [ No CAS ]
  • 5
  • [ 21211-65-4 ]
  • [ 19955-99-8 ]
  • 5,15-bis(3-vinylphenyl)porphyrin [ No CAS ]
  • 7
  • [ 19955-99-8 ]
  • C50H55NO14 [ No CAS ]
  • 8
  • [ 19955-99-8 ]
  • [ 360075-35-0 ]
  • 9
  • [ 19955-99-8 ]
  • [ 860782-73-6 ]
  • 10
  • [ 19955-99-8 ]
  • [5-cyano-10,20-bis(3-vinyl-phenyl)porphinato]zinc(II) [ No CAS ]
  • 11
  • [ 19955-99-8 ]
  • [5,15-dicyano-10,20-bis(3-vinylphenyl)porphinato]zinc(II) [ No CAS ]
  • 12
  • [ 19955-99-8 ]
  • [ 115104-35-3 ]
  • 13
  • [ 19955-99-8 ]
  • [ 115104-34-2 ]
  • 14
  • [ 19955-99-8 ]
  • [ 143816-62-0 ]
  • 15
  • [ 761449-24-5 ]
  • [ 19955-99-8 ]
  • C71H115N11O14 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 45℃; A solution of diene acetate from Example 2 (28 mg), <strong>[19955-99-8]3-vinylbenzaldehyde</strong> (0.015 ml,) and Hoveyda-Grubbs' catalyst (1.4 mg) in CH2Cl2 (2.0 ml) is heated under N2 at 45 C. overnight. Mass spectrometry analysis indicated that the reaction is complete. After cooling to room temperature, solvent is removed and the product is purified by preparative TLC (developed with 100% ethyl acetate. m/e+ for C71H115N11O14 1345.86, found 1346.70 (m+H)+, 1368.69 (m+Na)+. The acetyl protection group is removed by stirring with K2CO3 (12.9 mg) in MeOH (2 ml) over night. After removal of methanol, the residue is dissolved in ethyl acetate and filtered through a short silica gel pad. The crude product is purified by preparative TLC (developed with ethyl acetate). m/e+ for C69H113N11O3 1303.85, found 1304.66 (m+H)+, 1326.65 (m+Na)+, 1342.62 (m+K)+.
  • 16
  • [ 19955-99-8 ]
  • [ 120386-00-7 ]
  • [ 115104-31-9 ]
YieldReaction ConditionsOperation in experiment
With p-toluenesulfonic acid monohydrate; In diethyl ether; hexane; ethylene glycol; benzene; Step 2 Preparation of 2-(3-ethenylphenyl)-1,3-dioxolane To a solution of <strong>[19955-99-8]3-ethenylbenzaldehyde</strong> from Step 1 (3.77 g) and ethylene glycol (1.8 mL) in benzene (40 mL) was added p-toluenesulfonic acid monohydrate (100 mg). The reaction mixture was heated to reflux for 6 hours. The water produced by the reaction was collected in a Dean-Stark trap. The reaction was allowed to cool to room temperature. The reaction was diluted with NH4 OAc buffer and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated. Flash chromatography of the residue using 15% diethyl ether in hexane afforded the title compound.
  • 17
  • [ 937383-49-8 ]
  • [ 19955-99-8 ]
  • C27H33N5O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With N-ethyl-N,N-diisopropylamine;palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 20 - 105℃; for 6h; Step 4 Heck CouplingTo a solution of λ/-[3-lodo-6-(4-methyl-piperazin-1-yl)-1-(tetrahydro-pyran-2-yl)- 1H-indazol-5-yl]-methanesulfonamide (0.91g, 1.75 mmol) in dry DMF (10 mL) at ambient temperature was added 3-vinyl-benzaldehyde (0.35 g, 2.63 mmol) and DIEA (0.68 g, 5.26 mmol), followed by addition of Pd(OAc)2 (0.0196g, 0.0876 mmol) and P(o-toly)3 (0.159 g, 0.526 mmol). The resulting mixture was stirred at 105 0C for 6 hours. The reaction mixture was cooled to 0 0C and quenched with sat. NaHCO3 (1 OmL). The product was extracted with CH2CI2 thrice and the combined organic extracts were washed with H2O followed by brine, dried over Na2SO4 and concentrated under reduced pressure to furnish a solid, which was purified by column (CH2CI2/acetone) to obtain 3-{2-[6-(4-Methyl- <n="57"/>piperazin-1 -yl)-5-nitro-1 -(tetrahydro-pyran-2-yl)-1 H-indazol-3-yl]-vinyl}-benzaldehyde (0.37 g, 40 % yield) . MS (m/z): 476 (MH)+.
  • 18
  • [ 19955-99-8 ]
  • [ 89343-06-6 ]
  • [ 1115020-88-6 ]
  • 19
  • [ 19955-99-8 ]
  • [ 45804-94-2 ]
YieldReaction ConditionsOperation in experiment
99% With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; In tetrahydrofuran; at 60℃; for 2h;Schlenk technique; Inert atmosphere; General procedure: Fe(BF4)2·6H2O (0.7 mg; 0.002 mmol) and tris[2-(diphenyl-phosphino)-ethyl]phosphine [P(CH2CH2PPh2)3; tetraphos] (1.4 mg; 0.002 mmol) are placed in a Schlenk-tube under argon atmosphere. 1 mL dry tetrahydrofurane is added and the purple solution is stirred for 2 min. Cinnamaldehyde (63 μL; 0.5 mmol) and 100 μL n-hexadecane as an internal GC-standard are injected and a sample is taken for GC-analysis. The solution is heated to 60 C and the reaction starts by addition of 1.1 equiv formic acid (22 μL; 0.55 mmol). After 2 h, a second sample is taken for GC-analysis and conversion and yield are determined by comparison with authentic samples. For the isolation, the reaction is scaled up by a factor of 20. When the reaction is completed, the reaction solution is diluted with a mixture of n-hexane and ethyl acetate (3:1), filtered through a plug of silica and the solvent removed in vacuum.
99% With methanol; at 22℃; for 1h;Inert atmosphere; NaBH4 (327 mg, 8.66 mmol) was slowly added to a solution of 3- vinylbenzaldehyde (1.00 mL, 7.87 mmol) in MeOH (20 mL) at 22 C under N2. The mixture was stirred at 22 C for 1 h and concentrated under reduced pressure. The residue was purified by S1O2 chromatography (EA/ hexanes) to provide 1.05 g (99 %) of (3-vinylphenyl) methanol (INT 59-1). LCMS-ESI (m/z) mass not observed, tR = 2.00 min (Method 13). NMR (400 MHz, CDCh) d 7.42 (s, 1H), 7.37 - 7.30 (m, 2H), 7.26 (d, J = 3.1 Hz, 1H), 6.73 (dd, J = 17.6, 10.9 Hz, 1H), 5.78 (dd, J = 17.6, 0.9 Hz, 1H), 5.27 (dd, J = 10.9, 0.9 Hz, 1H), 4.70 (s, 2H), 1.67 (s, 1H).
  • 20
  • [ 19955-99-8 ]
  • [ 182500-35-2 ]
  • [ 1140904-61-5 ]
  • 22
  • [ 937383-69-2 ]
  • [ 19955-99-8 ]
  • [ 1228078-87-2 ]
  • 23
  • [ 19955-99-8 ]
  • [ 501-65-5 ]
  • [ 1221442-04-1 ]
  • 24
  • [ 1058181-02-4 ]
  • [ 19955-99-8 ]
  • C49H42N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Macrocyclic Compound (K) was synthesized in accordance with the following reaction formula. [Show Image] Into 30 mL of dichloromethane were dissolved 0.121 g of Compound (B) and 0.030 g of <strong>[19955-99-8]3-vinylbenzaldehyde</strong> (manufactured by Aldrich), and the solution was stirred for 24 hours at room temperature after adding one drop of trifluoroacetic acid. Then, into the solution was added 0.050 g of chloranil, and further the solution was stirred for 24 hours at room temperature. Thereafter, dichloromethane was distilled off, and the resultant black residue was purified through a silica gel column to yield Macrocyclic Compound (K). 1H-NMR(300MHz,CDCl3)δ1.42(s,18H), 5.34(d,J=10.8Hz,1H), 5.87(d,J=17.8Hz,1H), 6.65(d,J=4.2Hz,2H), 6.86(dd,J1=17.8Hz,J2=10.8Hz1 H), 6.95(d,J=4.2Hz,2H), 7.46-7.62(m,6H), 7.90(s,4H), 7.81 (s,4H), 8.01 (d,J=8.6Hz,2H), 8.13(d,J=8.8Hz,2H)
  • 25
  • [ 3132-99-8 ]
  • [ 7486-35-3 ]
  • [ 19955-99-8 ]
  • 26
  • [ 19955-99-8 ]
  • [ 622-88-8 ]
  • [ 1290610-42-2 ]
  • 27
  • [ 19955-99-8 ]
  • [ 469873-52-7 ]
  • [ 1314797-79-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 1-C-(β-D-galactopyranosyl)-propan-2-one (1 mmol, 220 mg) in anhydrous methanol (5 mL) was added LiOH*H2O (0.1 mmol) and was stirred for 10 min followed by the addition of the desired piperonal (1 mmol, 150 mg). The reaction mixture was stirred at room temperature for 45 min. After the completion of the reaction, it was quenched with Dowex 50WX8-200 (H+) resin and the resin was filtered off. The filtrate was concentrated under reduced pressure and was subjected to chromatographic purification to get the pure product (230 mg, 65% β-isomer).
  • 28
  • [ 1232225-20-5 ]
  • [ 19955-99-8 ]
  • [ 1232222-82-0 ]
YieldReaction ConditionsOperation in experiment
74% acetic acid; In ethanol; at 1 - 30℃; for 3h; To a solution of (7-morpholin-4-yl-2-pyridin-4-yl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine (20 mg, 0.064 mM) in ethanol (2.0 mL), there were added 3-vinyl-benzaldehyde (17 mg, 13 mM) and acetic acid (5.0 μL) and then the mixture was stirred at room temperature for 3 hours. The precipitated solid was recovered through filtration and then washed with ethanol to thus give the title compound (20 mg, yield: 74%). 1H-NMR (300 MHz, DMSO): δ 3.75-3.77 (4H, m), 3.88-3.90 (4H, m), 5.34 (1H, J=11.4 Hz, d), 5.93 (1H, J=17.7 Hz, d), 6.40 (1H, s), 6.77 (1H, s), 6.81 (1H, J=11.4, 17.7 Hz, dd), 7.42 (1H, J=7.8 Hz, t), 7.50 (1H, J=7.8 Hz, d), 7.68 (1H, J=7.8 Hz, d), 7.75 (1H, s), 7.91 (1H, J=1.5 Hz, d), 7.92 (1H, J=1.5 Hz, d), 8.10 (1H, s), 8.65 (1H, J=1.5 Hz, d), 8.67 (1H, J=1.5 Hz, d), 11.35 (1H, s) MS (ESI) m/z (M+H)+ 426
  • 29
  • [ 434-45-7 ]
  • [ 19955-99-8 ]
  • [ 1359217-53-0 ]
  • 30
  • [ 19955-99-8 ]
  • [ 1359217-31-4 ]
  • 31
  • [ 19955-99-8 ]
  • [ 111324-03-9 ]
  • [ 1392406-50-6 ]
  • 32
  • [ 19955-99-8 ]
  • [ 1313014-23-1 ]
  • [ 1313014-04-8 ]
YieldReaction ConditionsOperation in experiment
72% With acetic acid; In ethanol; at 20℃; for 3h; Example 19 Synthesis of N-(3-vinyl-benzvlidene)-N-(8-mor-pholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine (Compound 19) 3-Vinylbenzaldehyde (17mg, 0.13mmol) and an acetic acid (5.0 μL) were added to an ethanol solution (2.0mL) of (8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine (20mg, 0.064mmol), and stirred at room temperature for 3 hours. The precipitated solid material was filtered and washed with ethanol to obtain a title compound (20mg, 72%). 1H-NMR (300MHz, DMSO) : δ 3.85-3.87 (4H, m), 3.99-4.02 (4H, m), 5.33 (1H, J = 11.4Hz, d), 5.92 (1H, J = 17.4Hz, d), 6.49 (1H, s), 6.80 (1H, J = 10.5, 17.4Hz, dd), 7.41 (1H, J = 7.5Hz, t), 7.45 (1H, J = 8.1Hz, d), 7.66 (1H, J = 8.1Hz, d), 7.71 (1H, s), 7.88 (1H, s), 7.90 (1H, s), 8.05 (1H, s), 8.58-8.59 (3H, m), 11.04 (1H, s) MS(ESI) m/z (M+H)+ 426
  • 33
  • [ 18292-38-1 ]
  • [ 19955-99-8 ]
  • [ 1448863-11-3 ]
  • 35
  • [ 19955-99-8 ]
  • Umemoto's reagent [ No CAS ]
  • [ 75-05-8 ]
  • [ 1431153-04-6 ]
 

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