52684-34-1

Usage

Uses

Fluorescent monomer

InChI:InChI=1/C13H10O2/c1-2-13(14)15-12-8-7-10-5-3-4-6-11(10)9-12/h2-9H,1H2

Synthetic route

acrylic acid (79-10-7) + β-naphthol (135-19-3) → 2-naphthyl acrylate (52684-34-1)

Conditions	Yield
With magnesium hydroxide; di-tert-butyl dicarbonate; lithium carbonate at 25℃; for 24h; Reagent/catalyst;	95%

acryloyl chloride (814-68-6) + β-naphthol (135-19-3) → 2-naphthyl acrylate (52684-34-1)

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 (79-10-7) + β-naphthol (135-19-3) → 2-naphthyl acrylate (52684-34-1) + β-Naphthyl-β-chlorpropionat (111709-01-4)

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 (814-68-6) + β-naphthol (135-19-3) → 2-naphthyl acrylate (52684-34-1) + β-Naphthyl-β-chlorpropionat (111709-01-4)

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 (1056904-02-9) + 2-naphthyl acrylate (52684-34-1) → (R)-naphthalen-2-yl 2-((4-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-26-6)

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%

2-naphthyl acrylate (52684-34-1) + C16H29NO4S2Si (1241834-17-2) → C23H33NO4SSi (1241833-84-0)

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 (52684-34-1) + C18H23NO5S2 (1241834-07-0) → C25H27NO5S (1056904-26-7) + C19H16O4S (1241833-79-3)

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 (52684-34-1) + (E)-N-benzylidenemethanesulfonamide (73845-05-3) → C21H19NO4S (1268833-10-8)

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%

1-benzylisatin (1217-89-6) + 2-naphthyl acrylate (52684-34-1) → C28H21NO4 (1263090-11-4)

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 (52684-34-1) + N-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-4-methoxy-benzenesulfonamide → (R)-naphthalen-2-yl 2-((4-fluorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-24-4)

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%

C15H15NO3S (1056904-04-1) + 2-naphthyl acrylate (52684-34-1) → C28H25NO5S (1056904-18-7)

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 (52684-34-1) + N-benzylidene-4-methoxy-benzenesulfonamide (52960-60-8) → naphthalen-2-yl (S)-2-((4-Methoxyphenylsulfonamido)(phenylmethyl))acrylate (1056904-12-1)

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%

2-naphthyl acrylate (52684-34-1) + C21H27NO5S2 (1241834-11-6) → C28H31NO5S (1056904-27-8)

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 (52684-34-1) + C15H12F3NO3S → (R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(2-(trifluoromethyl)phenyl)methyl)acrylate (1268833-30-2)

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 (52684-34-1) + C14H12ClNO3S → (S)-naphthalen-2-yl 2-((2-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-31-3)

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 (52684-34-1) + C14H12FNO3S → (S)-naphthalen-2-yl 2-((2-fluorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-33-5)

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 (52684-34-1) + C12H11NO3S2 → (S)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(thiophen-2-yl)methyl)acrylate (1268833-35-7)

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 (52684-34-1) + C14H12BrNO3S → (R)-naphthalen-2-yl 2-((4-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-25-5)

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%

(E)-N-(furan-2-ylmethylene)-4-methoxybenzenesulfonamide + 2-naphthyl acrylate (52684-34-1) → (S)-naphthalen-2-yl 2-(furan-2-yl(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-34-6)

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 (52684-34-1) + C15H12F3NO3S (1191127-92-0) → (R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(4-(trifluoromethyl)phenyl)methyl)acrylate (1268833-27-7)

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 (52684-34-1) + C14H12BrNO3S (1191127-96-4) → (S)-naphthalen-2-yl 2-((2-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-32-4)

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 (861145-19-9) + 2-naphthyl acrylate (52684-34-1) → (R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(p-tolyl)methyl)acrylate (1268833-22-2)

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 (1056904-01-8) + 2-naphthyl acrylate (52684-34-1) → C28H25NO5S (1056904-13-2)

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 (52684-34-1) + C16H17NO3S → (R)-naphthalen-2-yl 2-((4-ethylphenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-23-3)

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 (52684-34-1) + (E)-N-benzylidene-4-methoxybenzene sulfonamide → (R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(phenyl)methyl)acrylate (1268833-09-5)

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 (52684-34-1) + 4-nitro-N-[(1E)-phenylmethylidene]benzene-1-sulfonamide (63160-16-7) → C26H20N2O6S (1268849-55-3)

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 (52684-34-1) + C14H12ClNO3S → (R)-naphthalen-2-yl 2-((3-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-29-9)

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 (4290-94-2) + 2-naphthyl acrylate (52684-34-1) → naphthalen-2-yl 2-(1-ethyl-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acrylate (1392206-63-1)

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%

2-naphthyl acrylate (52684-34-1) + N,N-di(buta-2,3-dien-1-yl)-4-methylbenzenesulfonamide → C28H27NO4S

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 (1056904-03-0) + 2-naphthyl acrylate (52684-34-1) → naphthalen-2-yl (S)-2-((3-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1056904-17-6)

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 (52684-34-1) + 4-Methoxy-N-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-benzenesulfonamide (73845-03-1) → naphthalen-2-yl (S)-2-((4-methoxyphenyl)(4-methoxyphenylsulfonamido)methyl)-acrylate (1056904-16-5)

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 (52684-34-1) + C14H12ClNO3S (1191127-93-1) → (R)-naphthalen-2-yl 2-((4-chlorophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate (1268833-26-6)

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 (52684-34-1) + C14H12N2O5S (1312951-18-0) → (R)-naphthalen-2-yl 2-((4-methoxyphenylsulfonamido)(4-nitrophenyl)methyl)acrylate (1268849-56-4)

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%

Upstream product

• 79-10-7 acrylic acid 
• 135-19-3 β-naphthol 
• 814-68-6 acryloyl chloride 

Downstream Products

• 1056904-13-2 C₂₈H₂₅NO₅S 
• 1056904-14-3 C₂₇H₂₂ClNO₅S 
• 1056904-15-4 C₂₇H₂₂N₂O₇S 
• 1056904-17-6 naphthalen-2-yl (S)-2-((3-bromophenyl)(4-methoxyphenylsulfonamido)methyl)acrylate 
• 1056904-18-7 C₂₈H₂₅NO₅S 
• 1056904-20-1 C₂₅H₂₁NO₆S 
• 1056904-21-2 naphthalen-2-yl (S)-2-(((4-methoxyphenyl)sulfonamido)(naphthalen-2-yl)methyl)-acrylate 
• 1056904-12-1 naphthalen-2-yl (S)-2-((4-Methoxyphenylsulfonamido)(phenylmethyl))acrylate 
• 1056904-16-5 naphthalen-2-yl (S)-2-((4-methoxyphenyl)(4-methoxyphenylsulfonamido)methyl)-acrylate 
• 1056904-25-6 C₂₄H₂₅NO₅S 
• 1056904-24-5 C₂₅H₂₇NO₅S 
• 1056904-26-7 C₂₅H₂₇NO₅S 
• 1241833-79-3 C₁₉H₁₆O₄S 
• 1056904-27-8 C₂₈H₃₁NO₅S 

Relevant academic research and scientific papers

CARBOXYLIC ACID ESTER PRODUCTION METHOD

Provided is a production method whereby corresponding carboxylic acid esters can be obtained from a variety of carboxylic acids at a high yield, even under conditions using a simple reaction operation and little catalyst and even if the amount of substrate used is theoretical. A production method for carboxylic acid ester, whereby a prescribed diester dicarbonate, carboxylic acid, and alcohol are reacted in the presence of at least one type of magnesium compound and at least one type of alkali metal compound.

(Meth) acrylate compound -2 - naphthyl substituted oxy, its manufacture and use (by machine translation)

[Problem] S no unpleasant odor peculiar to the heteroatoms such as, halogen-free from the friendly to the environment, and, (meth) acrylate compound having a high refractive index aromatic. (Meth) acrylates of formula (1) is represented by [a] -2 - naphthyl substituted oxy compounds. (R1 Is H or a methyl group; R2 Is H or an alkyl group of C1 a-8; R3 The alkyl groups of C1 a-8, alkylcarbonyl groups or allyl carbonyl group)[Drawing] no (by machine translation)

MONOHYDROXY-2-NAPHTHYL(METH)ACRYLATE COMPOUND, METHOD FOR PRODUCING THE SAME AND USE THEREFOR

PROBLEM TO BE SOLVED: To provide an aromatic (meth)acrylate compound that is free from an unpleasant odor peculiar to hetero atoms such as sulfur atoms, is environmentally friendly as it contains no halogen atom, has a high refractive index, and also has excellent adhesion. SOLUTION: The present invention provides a monohydroxy-2-naphthyl(meth)acrylate compound represented by formula (1) (R1 is H or a methyl group; R2 is H or a C1-8 alkyl group). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Enantioselective organocatalytic Michael additions to acrylic acid derivatives: Generation of all-carbon quaternary stereocentres

Acrylic esters, thioesters and N-acryloyl pyrrole have been identified as effective electrophiles in the enantioselective Michael addition reaction with β-keto ester pro-nucleophiles catalysed by a cinchona alkaloid derived bifunctional organocatalyst; enantiomeric excesses of up to 98% and yields of up to 96% can be obtained for a range of Michael acceptors and pro-nucleophiles. The Royal Society of Chemistry.