Conditions | Yield |
---|---|
With magnesium hydroxide; di-tert-butyl dicarbonate; lithium carbonate at 25℃; for 24h; Reagent/catalyst; | 95% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Inert atmosphere; | 82% |
With triethylamine In acetone at 20℃; for 0.5h; Inert atmosphere; | 1.32 g |
With triethylamine In acetone at 20℃; for 0.5h; Inert atmosphere; | 1.32 g |
acrylic acid
β-naphthol
A
2-naphthyl acrylate
B
β-Naphthyl-β-chlorpropionat
Conditions | Yield |
---|---|
With phosphorus pentachloride In neat (no solvent) 1.) 110-120 deg C, 1 h, 2.) room temp., 2.5 h then 90 deg C, 3 h; | A n/a B 43% |
acryloyl chloride
β-naphthol
A
2-naphthyl acrylate
B
β-Naphthyl-β-chlorpropionat
Conditions | Yield |
---|---|
With aluminium trichloride In neat (no solvent) 1.) 80-90 deg C, 3 h, 2.) 100 deg C, 1 h; | A n/a B 43% |
N-(4-chlorobenzylidene)-4-methoxybenzenesulfonamide
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With tert-butyl (2-((4-((1R)-7-ethylhexahydro-1H-3,7-methanopyrrolo[2,1-c][1,4]oxazin-1-yl)quinolin-6-yl)amino)-2-oxoethyl)carbamate; β-naphthol In dichloromethane at -30℃; for 48h; Morita-Baylis-Hillman Alkylation; Inert atmosphere; enantioselective reaction; | 100% |
Conditions | Yield |
---|---|
With C26H27N3O2; β-naphthol In dichloromethane at 10℃; for 12h; Aza-Morita-Baylis-Hillman reaction; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
2-naphthyl acrylate
C18H23NO5S2
A
C25H27NO5S
B
C19H16O4S
Conditions | Yield |
---|---|
With C26H27N3O2; β-naphthol In dichloromethane at 10℃; for 12h; Aza-Morita-Baylis-Hillman reaction; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | A 99% B n/a |
2-naphthyl acrylate
(E)-N-benzylidenemethanesulfonamide
C21H19NO4S
Conditions | Yield |
---|---|
With (S)-N-(1-(diphenylphosphanyl)-3-methylbutan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at 20℃; for 24h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With 4-(3-ethyl-4-oxa-1-azatricyclo[4,4,0,0(3,8)]dec-5-yl)quinolin-6-ol In dichloromethane at 20℃; for 40h; asymmetric Morita-Baylis-Hillman reaction; optical yield given as %ee; enantioselective reaction; | 97% |
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-fluorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 96% |
Conditions | Yield |
---|---|
With 6'-N-boc-glycine-β-ICD; β-naphthol In dichloromethane at -30℃; for 68h; Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
N-benzylidene-4-methoxy-benzenesulfonamide
naphthalen-2-yl (S)-2-((4-Methoxyphenylsulfonamido)(phenylmethyl))acrylate
Conditions | Yield |
---|---|
With 6'-N-boc-glycine-β-ICD; β-naphthol In dichloromethane at -30℃; Reactivity; Reagent/catalyst; Solvent; Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With C26H27N3O2; β-naphthol In dichloromethane at 10℃; for 12h; Aza-Morita-Baylis-Hillman reaction; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(2-(trifluoromethyl)phenyl)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
(S)-naphthalen-2-yl 2-((2-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
(S)-naphthalen-2-yl 2-((2-fluorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
(S)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(thiophen-2-yl)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
2-naphthyl acrylate
(S)-naphthalen-2-yl 2-(furan-2-yl(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 93% |
2-naphthyl acrylate
C15H12F3NO3S
(R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(4-(trifluoromethyl)phenyl)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 93% |
2-naphthyl acrylate
C14H12BrNO3S
(S)-naphthalen-2-yl 2-((2-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 93% |
(E)-4-methoxy-N-((E)-p-tolylethylidene)benzenesulfonamide
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(p-tolyl)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 91% |
4-methoxy-N-(4-methylbenzylidene)benzenesulfonamide
2-naphthyl acrylate
C28H25NO5S
Conditions | Yield |
---|---|
With 6'-N-boc-glycine-β-ICD; β-naphthol In dichloromethane at -30℃; for 67h; Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 90% |
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-ethylphenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 90% |
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(phenyl)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 89% |
2-naphthyl acrylate
4-nitro-N-[(1E)-phenylmethylidene]benzene-1-sulfonamide
C26H20N2O6S
Conditions | Yield |
---|---|
With (S)-N-(1-(diphenylphosphanyl)-3-methylbutan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at 20℃; for 24h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 88% |
2-naphthyl acrylate
(R)-naphthalen-2-yl 2-((3-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 85% |
N-ethylisatin
2-naphthyl acrylate
naphthalen-2-yl 2-(1-ethyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acrylate
Conditions | Yield |
---|---|
With BF4(1-)*C9H19N2O(1+); 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 0.416667h; Baylis-Hillman reaction; | 85% |
Conditions | Yield |
---|---|
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen In tetrahydrofuran; dichloromethane at 40℃; for 16h; regioselective reaction; | 85% |
C14H12BrNO3S
2-naphthyl acrylate
naphthalen-2-yl (S)-2-((3-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With 6'-N-boc-glycine-β-ICD; β-naphthol In dichloromethane at -30℃; for 72h; Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 84% |
2-naphthyl acrylate
4-Methoxy-N-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-benzenesulfonamide
naphthalen-2-yl (S)-2-((4-methoxyphenyl)(4-methoxyphenylsulfonamido)methyl)-acrylate
Conditions | Yield |
---|---|
With 6'-N-boc-glycine-β-ICD; β-naphthol In dichloromethane at -30℃; for 80h; Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 84% |
2-naphthyl acrylate
C14H12ClNO3S
(R)-naphthalen-2-yl 2-((4-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 84% |
2-naphthyl acrylate
C14H12N2O5S
(R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(4-nitrophenyl)methyl)acrylate
Conditions | Yield |
---|---|
With N-((2S,3R)-3-((2,3-dimethylbutan-2-yl)dimethylsilyloxy)-1-(diphenylphosphino)butan-2-yl)-4-methylbenzenesulfonamide In tetrahydrofuran at -30℃; for 48h; Aza-Morita-Baylis-Hillman reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 84% |
The 2-Propenoic acid, 2-naphthalenyl ester, with the CAS registry number 52684-34-1, is also known as 2-Naphthyl acrylate. It belongs to the product categories of Monomer; C12 to C63 Photonic and Optical Materials; Carbonyl Compounds; Esters; Photoluminescent Materials > Fluorescent Monomers. This chemical's molecular formula is C13H10O2 and molecular weight is 198.22. What's more, its IUPAC name is called 2-Naphthyl acrylate.
Physical properties about 2-Propenoic acid, 2-naphthalenyl ester are: (1)ACD/LogP: 3.171; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.17; (4)ACD/LogD (pH 7.4): 3.17; (5)ACD/BCF (pH 5.5): 151.26; (6)ACD/BCF (pH 7.4): 151.26; (7)ACD/KOC (pH 5.5): 1264.33; (8)ACD/KOC (pH 7.4): 1264.33; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.609; (14)Molar Refractivity: 59.795 cm3; (15)Molar Volume: 172.778 cm3; (16)Polarizability: 23.704×10-24cm3; (17)Surface Tension: 42.602 dyne/cm; (18)Density: 1.147 g/cm3; (19)Flash Point: 143.685 °C; (20)Enthalpy of Vaporization: 58.949 kJ/mol; (21)Boiling Point: 345.426 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C(Oc2ccc1c(cccc1)c2)\C=C
(2) InChI: InChI=1S/C13H10O2/c1-2-13(14)15-12-8-7-10-5-3-4-6-11(10)9-12/h2-9H,1H2
(3) InChIKey: SLVJUZOHXPZVLR-UHFFFAOYSA-N
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