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3-Benzoylacrylic acid is an organic compound with the chemical formula C11H10O3. It is a derivative of acrylic acid, featuring a benzoyl group attached to the third carbon atom. This molecule is known for its potential applications in various chemical and pharmaceutical processes due to its unique structure and reactivity.

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  • 583-06-2 Structure
  • Basic information

    1. Product Name: 3-BENZOYLACRYLIC ACID
    2. Synonyms: (2E)-4-Oxo-4-phenyl-2-butenoic acid;3-benzoyl-acrylicaci;4-oxo-4-phenyl-2-butenoicaci;4-phenyl-4-oxo-2-butenoicacid;Acrylic acid, 3-benzoyl-;beta-Benzoylacrylsaeure;Crotonic acid, 4-oxo-4-phenyl-;BENZOYL ACRYLIC ACID
    3. CAS NO:583-06-2
    4. Molecular Formula: C10H8O3
    5. Molecular Weight: 176.17
    6. EINECS: 209-496-5
    7. Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
    8. Mol File: 583-06-2.mol
  • Chemical Properties

    1. Melting Point: 94-97 °C(lit.)
    2. Boiling Point: 267.77°C (rough estimate)
    3. Flash Point: 170 °C
    4. Appearance: Yellow to yellow-brown cryst. needles or powde
    5. Density: 1.1958 (rough estimate)
    6. Vapor Pressure: 5.23E-05mmHg at 25°C
    7. Refractive Index: 1.5036 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 3.43±0.10(Predicted)
    11. Water Solubility: Insoluble in water.
    12. BRN: 1817876
    13. CAS DataBase Reference: 3-BENZOYLACRYLIC ACID(CAS DataBase Reference)
    14. NIST Chemistry Reference: 3-BENZOYLACRYLIC ACID(583-06-2)
    15. EPA Substance Registry System: 3-BENZOYLACRYLIC ACID(583-06-2)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. RIDADR: UN 2811 6.1/PG 3
    5. WGK Germany: 3
    6. RTECS: EM9259050
    7. TSCA: Yes
    8. HazardClass: 6.1
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 583-06-2(Hazardous Substances Data)

583-06-2 Usage

Uses

Used in Chemical Synthesis:
3-Benzoylacrylic acid is used as a key intermediate in the synthesis of various organic compounds. Its reactive sites allow it to participate in a range of chemical reactions, facilitating the creation of new molecules with diverse applications.
Used in Pharmaceutical Industry:
3-Benzoylacrylic acid is used as a building block in the development of pharmaceuticals. Its ability to form covalent bonds with other molecules makes it a valuable component in the design of drugs targeting specific biological pathways.
Used in Material Science:
In the field of material science, 3-benzoylacrylic acid is utilized for the development of novel materials with unique properties. Its incorporation into polymers and other materials can lead to enhanced characteristics such as improved strength, flexibility, or chemical resistance.
Used in Research and Development:
3-Benzoylacrylic acid serves as a valuable compound in academic and industrial research settings. Its reactivity and structural features make it an interesting subject for studies aimed at understanding new chemical reactions or developing innovative applications.
In the specific reaction mentioned in the provided materials, 3-benzoylacrylic acid (2-butenoic acid, 4-oxo-4-phenyl-) can react with morpholine to obtain 2-morpholin-4-yl-4-oxo-4-phenyl-butyric acid. This reaction requires the use of solvents such as toluene and ethanol to facilitate the process. This reaction exemplifies the synthetic utility of 3-benzoylacrylic acid in creating complex organic molecules for various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 583-06-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 583-06:
(5*5)+(4*8)+(3*3)+(2*0)+(1*6)=72
72 % 10 = 2
So 583-06-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H8O3/c11-9(6-7-10(12)13)8-4-2-1-3-5-8/h1-7H,(H,12,13)/p-1/b7-6+

583-06-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A11147)  3-Benzoylacrylic acid, predominantly trans, 97%   

  • 583-06-2

  • 5g

  • 701.0CNY

  • Detail
  • Alfa Aesar

  • (A11147)  3-Benzoylacrylic acid, predominantly trans, 97%   

  • 583-06-2

  • 25g

  • 2008.0CNY

  • Detail
  • Alfa Aesar

  • (A11147)  3-Benzoylacrylic acid, predominantly trans, 97%   

  • 583-06-2

  • 100g

  • 7379.0CNY

  • Detail

583-06-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-4-oxo-4-phenylbut-2-enoic acid

1.2 Other means of identification

Product number -
Other names 2-Butenoic acid, 4-oxo-4-phenyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:583-06-2 SDS

583-06-2Synthetic route

maleic anhydride
108-31-6

maleic anhydride

benzene
71-43-2

benzene

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With aluminum (III) chloride at 80℃; for 0.5h;85%
With aluminium trichloride In carbon disulfide at 5℃;60%
acetophenone
98-86-2

acetophenone

Glyoxilic acid
298-12-4

Glyoxilic acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetic acid for 18h; Reflux;81%
at 100 - 105℃; for 2h;
styrylacetic acid
2243-53-0

styrylacetic acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With water; iodine; sodium carbonate; potassium iodide
2-hydroxy-4-oxo-4-phenyl-butyric acid
65245-10-5

2-hydroxy-4-oxo-4-phenyl-butyric acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With sulfuric acid at 0℃; anschliessend in Eiswasser giessen;
4-hydroxy-4-phenylbut-2-enoic acid
99389-54-5

4-hydroxy-4-phenylbut-2-enoic acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With iodine; sodium carbonate
3-bromo-4-oxo-4-phenylbutanoic acid
53515-22-3

3-bromo-4-oxo-4-phenylbutanoic acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With sodium acetate; acetic acid
(α-bromo-cis-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride

(α-bromo-cis-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride

acetic acid
64-19-7

acetic acid

A

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

B

(E)-2-Bromo-3-phenyl-acrylic acid
15894-30-1

(E)-2-Bromo-3-phenyl-acrylic acid

(α-bromo-trans-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride

(α-bromo-trans-cinnamic acid )-(4-oxo-4-phenyl-crotonic acid )-anhydride

acetic acid
64-19-7

acetic acid

A

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

B

(Z)-2-bromo-3-phenylacrylic acid
15813-24-8

(Z)-2-bromo-3-phenylacrylic acid

3-bromo-4-oxo-4-phenylbutanoic acid
53515-22-3

3-bromo-4-oxo-4-phenylbutanoic acid

sodium acetate
127-09-3

sodium acetate

acetic acid
64-19-7

acetic acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

maleic anhydride
108-31-6

maleic anhydride

1-bromocyclohexa-1,4-diene
95896-86-9

1-bromocyclohexa-1,4-diene

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
(i) AgSbF6, SO2, (ii) /BRN= 106909/; Multistep reaction;
4,4-Dimethoxy-4-phenyl-crotonsaeure-aethylester
33093-73-1

4,4-Dimethoxy-4-phenyl-crotonsaeure-aethylester

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With formic acid; sulfuric acid at 100℃; for 1h;
ethyl 3-benzoyl acrylate
15121-89-8, 20908-27-4, 17450-56-5

ethyl 3-benzoyl acrylate

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid Heating;
maleic anhydride
108-31-6

maleic anhydride

aluminium trichloride
7446-70-0

aluminium trichloride

benzene
71-43-2

benzene

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester
19522-28-2

(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester

diluted natrium carbonate

diluted natrium carbonate

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

styrylacetic acid
2243-53-0

styrylacetic acid

water
7732-18-5

water

iodine
7553-56-2

iodine

natrium carbonate

natrium carbonate

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

hydrogenchloride
7647-01-0

hydrogenchloride

(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester
19522-28-2

(Z)-4-oxo-4-phenyl-but-2-enoic acid methyl ester

A

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

B

2-hydroxy-4-oxo-4-phenyl-butyric acid
65245-10-5

2-hydroxy-4-oxo-4-phenyl-butyric acid

hydrogenchloride
7647-01-0

hydrogenchloride

methyl trans-β-benzoylacrylate
14274-07-8

methyl trans-β-benzoylacrylate

A

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

B

2-hydroxy-4-oxo-4-phenyl-butyric acid
65245-10-5

2-hydroxy-4-oxo-4-phenyl-butyric acid

sulfuric acid
7664-93-9

sulfuric acid

2-hydroxy-4-oxo-4-phenyl-butyric acid
65245-10-5

2-hydroxy-4-oxo-4-phenyl-butyric acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

α-bromo-β-benzoylpropionic acid
63104-90-5

α-bromo-β-benzoylpropionic acid

natrium carbonate

natrium carbonate

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

4-hydroxy-4-phenylbut-2-enoic acid
99389-54-5

4-hydroxy-4-phenylbut-2-enoic acid

iodine
7553-56-2

iodine

natrium carbonate

natrium carbonate

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
at 20℃;
ethanol
64-17-5

ethanol

β-benzoyl-acrylic acid-dibromide
22221-93-8, 22221-94-9, 99074-11-0

β-benzoyl-acrylic acid-dibromide

sodium thiosulfate

sodium thiosulfate

potassium iodide

potassium iodide

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

α-chloro-β-benzoylpropionic acid
90798-09-7

α-chloro-β-benzoylpropionic acid

natrium carbonate

natrium carbonate

A

hydrogenchloride
7647-01-0

hydrogenchloride

B

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

α-chloro-β-benzoylpropionic acid
90798-09-7

α-chloro-β-benzoylpropionic acid

water
7732-18-5

water

A

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

B

2-hydroxy-4-oxo-4-phenyl-butyric acid
65245-10-5

2-hydroxy-4-oxo-4-phenyl-butyric acid

phenylglyoxal dimethylacetal
19159-39-8

phenylglyoxal dimethylacetal

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene / 5.5 h / Heating
2: HCO2H, H2SO4 / 1 h / 100 °C
View Scheme
(2R)-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid
861896-81-3

(2R)-4-oxo-4-phenyl-2-{[(1R)-1-phenylethyl]amino}butanoic acid

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

morpholine
110-91-8

morpholine

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

2-Morpholino-4-oxo-4-phenyl-butansaeure
21813-61-6

2-Morpholino-4-oxo-4-phenyl-butansaeure

Conditions
ConditionsYield
In ethanol; toluene97%
With benzene
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

3-bromo-4-oxo-4-phenylbutanoic acid
53515-22-3

3-bromo-4-oxo-4-phenylbutanoic acid

Conditions
ConditionsYield
With bromine In acetic acid at 60℃;94%
piperidine
110-89-4

piperidine

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

4-Oxo-4-phenyl-2-piperidino-butansaeure
101105-59-3

4-Oxo-4-phenyl-2-piperidino-butansaeure

Conditions
ConditionsYield
In ethanol; toluene93%
With benzene
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

(2E)-1-phenyl-3-(2-naphthyl)-2-propen-1-one
42299-50-3, 53744-33-5

(2E)-1-phenyl-3-(2-naphthyl)-2-propen-1-one

Conditions
ConditionsYield
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;90%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

trans-4-methoxychalcone
22252-15-9

trans-4-methoxychalcone

Conditions
ConditionsYield
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;89%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-methyl ester

2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-methyl ester

Conditions
ConditionsYield
In benzene for 6h; other β-aroylacrylic acid or cinnamic acid, other phosphorane;88%
In benzene for 6h; Heating;88%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

para-bromotoluene
106-38-7

para-bromotoluene

(E)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one
22252-14-8, 72758-77-1, 4224-87-7

(E)-3-(4-methylphenyl)-1-phenyl-2-propen-1-one

Conditions
ConditionsYield
With sodium acetate; palladium diacetate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere;87%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-(4-chlorophenyl)-4-phenylbutane-1,4-dione
60721-33-7

1-(4-chlorophenyl)-4-phenylbutane-1,4-dione

Conditions
ConditionsYield
With sodium carbonate; triethylamine; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide In ethanol at 80℃; for 6h;86%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-ethyl ester

2-Phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-succinic acid 4-ethyl ester

Conditions
ConditionsYield
In benzene for 6h; Heating;85%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

6-(4-Chloro-phenyl)-4-(2-methoxy-4-methyl-phenyl)-1H-pyrimidine-2-thione
181763-50-8

6-(4-Chloro-phenyl)-4-(2-methoxy-4-methyl-phenyl)-1H-pyrimidine-2-thione

2-[4-(4-Chloro-phenyl)-6-(2-methoxy-4-methyl-phenyl)-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid
181763-69-9

2-[4-(4-Chloro-phenyl)-6-(2-methoxy-4-methyl-phenyl)-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid

Conditions
ConditionsYield
With piperidine In benzene for 6h; Heating;85%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

1-(4-thioxo-3,4-dihydroquinazolin-2-yl)heptadecane-1-sodium sulfonate

1-(4-thioxo-3,4-dihydroquinazolin-2-yl)heptadecane-1-sodium sulfonate

sodium 4-oxo-4-phenyl-2-[2-(1-sulfoheptadecyl)quinazolin-4-ylsulfanyl]butanoic acid

sodium 4-oxo-4-phenyl-2-[2-(1-sulfoheptadecyl)quinazolin-4-ylsulfanyl]butanoic acid

Conditions
ConditionsYield
In benzene at 20℃; for 48h;85%
With piperidine In benzene at 20℃; for 48h;85%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

ethyl (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)benzoate
87116-41-4

ethyl (E)-4-(3-oxo-3-phenylprop-1-en-1-yl)benzoate

Conditions
ConditionsYield
With sodium acetate; palladium diacetate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere;85%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

ammonium salt of N-o-anisylamino dithiocarbamic acid
49791-47-1

ammonium salt of N-o-anisylamino dithiocarbamic acid

3-(2-methoxyphenyl)-5-(2-oxo-2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one
1075256-86-8

3-(2-methoxyphenyl)-5-(2-oxo-2-phenylethyl)-2-thioxo-1,3-thiazolidin-4-one

Conditions
ConditionsYield
In ethanol at 20℃; for 0.5h;84%
pentanal
110-62-3

pentanal

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

1-Phenyl-1,4-octanedione
77588-52-4

1-Phenyl-1,4-octanedione

Conditions
ConditionsYield
With sodium carbonate; triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In ethanol at 80℃; for 6h;83%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

cyclohexanone
108-94-1

cyclohexanone

4-Oxo-2-(2-oxo-cyclohexyl)-4-phenyl-butyric acid
54469-72-6

4-Oxo-2-(2-oxo-cyclohexyl)-4-phenyl-butyric acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 30 - 40℃; for 1h;83%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

phenylboronic acid
98-80-6

phenylboronic acid

1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

Conditions
ConditionsYield
With palladium diacetate; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;83%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

2-N-Methylpiperazino-4-oxo-4-phenyl-butansaeure
35045-67-1

2-N-Methylpiperazino-4-oxo-4-phenyl-butansaeure

Conditions
ConditionsYield
In ethanol; toluene82%
furfural
98-01-1

furfural

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

1-(furan-2-yl)-4-phenylbutane-1,4-dione
77588-51-3

1-(furan-2-yl)-4-phenylbutane-1,4-dione

Conditions
ConditionsYield
With sodium carbonate; triethylamine; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide In ethanol at 80℃; for 6h;82%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

6-(4-Chloro-phenyl)-4-(4-methoxy-2-methyl-phenyl)-5,6-dihydro-1H-pyrimidine-2-thione
249526-05-4

6-(4-Chloro-phenyl)-4-(4-methoxy-2-methyl-phenyl)-5,6-dihydro-1H-pyrimidine-2-thione

2-[4-(4-Chloro-phenyl)-6-(4-methoxy-2-methyl-phenyl)-4,5-dihydro-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid

2-[4-(4-Chloro-phenyl)-6-(4-methoxy-2-methyl-phenyl)-4,5-dihydro-pyrimidin-2-ylsulfanyl]-4-oxo-4-phenyl-butyric acid

Conditions
ConditionsYield
With piperidine In benzene for 6h; Heating;82%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

α-chloro-β-benzoylpropionic acid
90798-09-7

α-chloro-β-benzoylpropionic acid

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 72h;81%
With hydrogenchloride; acetic acid
With hydrogenchloride
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

benzaldehyde
100-52-7

benzaldehyde

phenacylacetophenone
495-71-6

phenacylacetophenone

Conditions
ConditionsYield
With sodium carbonate; triethylamine; 3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide In ethanol at 80℃; for 6h;81%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

β-benzoyl-α-(diphenylphosphoryl)propionic acid
433942-28-0

β-benzoyl-α-(diphenylphosphoryl)propionic acid

Conditions
ConditionsYield
In benzene for 6h; Heating;81%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

3-benzoyl-2,3-dibromopropionic acid
99074-11-0

3-benzoyl-2,3-dibromopropionic acid

Conditions
ConditionsYield
With bromine In acetic acid at 20℃;80%
With bromine In chloroform at 20℃; for 3h;40.64%
With chloroform; bromine
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

butyraldehyde
123-72-8

butyraldehyde

1-phenylheptane-1,4-dione
63297-52-9

1-phenylheptane-1,4-dione

Conditions
ConditionsYield
With sodium carbonate; triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In ethanol at 80℃; for 6h;80%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

(Benzoylmethylene)triphenylphosphorane
20913-05-7

(Benzoylmethylene)triphenylphosphorane

4-Oxo-4-phenyl-2-phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-butyric acid

4-Oxo-4-phenyl-2-phenylacetyl-3-(triphenyl-λ5-phosphanylidene)-butyric acid

Conditions
ConditionsYield
In ethyl acetate for 10h; Heating;80%
thiophene
188290-36-0

thiophene

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

4-Oxo-4-phenyl-2-thiophen-2-yl-butyric acid
170874-98-3

4-Oxo-4-phenyl-2-thiophen-2-yl-butyric acid

Conditions
ConditionsYield
In benzene for 5h; Heating;80%
3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

para-bromoacetophenone
99-90-1

para-bromoacetophenone

(E)-3-(4-Acetylphenyl)-1-phenyl-prop-2-en-1-on
253597-40-9

(E)-3-(4-Acetylphenyl)-1-phenyl-prop-2-en-1-on

Conditions
ConditionsYield
With sodium acetate; palladium diacetate; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 120℃; for 4h; Inert atmosphere;80%
dimethyl 2,2'-azobis(isobutyrate)
2589-57-3

dimethyl 2,2'-azobis(isobutyrate)

3-benzoylacrylic acid
583-06-2

3-benzoylacrylic acid

(E)-methyl 2,2-dimethyl-5-oxo-5-phenylpent-3-enoate

(E)-methyl 2,2-dimethyl-5-oxo-5-phenylpent-3-enoate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; silver orthophosphate; copper(II) nitrate trihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Inert atmosphere;80%

583-06-2Relevant articles and documents

Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids

Lu, Yufei,Li, Jing,Zhu, Yue,Shen, Jiefeng,Liu, Delong,Zhang, Wanbin

supporting information, p. 3643 - 3649 (2019/05/29)

An asymmetric hydrogenation of aroylacrylic acids catalyzed by RuPHOX-Ru catalyst has been developed, affording the corresponding chiral γ-lactones in high yields and with up to 93% ee. The methodology has the advantage of utilizing easily accessible substrates and has therefore expand the scope of the resulting chiral γ-lactones. Furthermore, high catalytic efficiency was achieved in that the reduction of both the C[dbnd]C and C[dbnd]O double bonds was achieved in one step. The current work provides an alternative and convenient pathway for the synthesis of a wide range of chiral γ-lactones.

Photoinduced, Copper-Promoted Regio- and Stereoselective Decarboxylative Alkylation of α,β-Unsaturated Acids with Alkyl Iodides

Wang, Chao,Lei, Yingjie,Guo, Mengzhun,Shang, Qinyu,Liu, Hong,Xu, Zhaoqing,Wang, Rui

supporting information, p. 6412 - 6415 (2017/12/08)

The first example of UV light-induced, copper-catalyzed regio- and stereoselective decarboxylative coupling of α,β-unsaturated acids with alkyl iodides was reported. Under standard conditions, the 1°, 2°, and 3° alkyl iodides proceeded smoothly with the E-selective alkenes obtained in uniformly good yields and high stereoselectivities.

Synthesis, antioxidant and antimicrobial activities of novel thiopyrano[2,3-d]thiazoles based on aroylacrylic acids

Lozynskyi, Andrii,Zasidko, Viktoria,Atamanyuk, Dmytro,Kaminskyy, Danylo,Derkach, Halyna,Karpenko, Olexandr,Ogurtsov, Volodymyr,Kutsyk, Roman,Lesyk, Roman

, p. 427 - 436 (2017/05/29)

Abstract: Here it is described the synthesis, antioxidant and antimicrobial activity determination of novel rel-(5 R, 6 S, 7 R)-6-benzoyl-7-phenyl-2-oxo-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazole-5-carboxylic acids. The target compounds were obtained in good yields from 5-arylidene-4-thioxo-2-thiazolidinones and β -aroylacrylic acids via regio- and diastereoselective hetero-Diels–Alder reaction. The stereochemistry of the cycloaddition was confirmed by NMR spectra. The antioxidant and antimicrobial activity screening identified 7 compounds (3c, 3e, 3f, 3g, 3k, 3l, 3p) with a high level of free radical scavenging (43–77% DPPH assay), and compounds with significant influence on Staphylococcus aureus, Bacillus subtilis and Candida albicans (MIC 3.13–6.25 μ g/mL), but slight effect on Escherichia coli.

Synthesis of 1,5-benzodiazepine derivatives using p-toluenesulfonic acid as catalyst

Wang, Shasha,Hu, Lijuan,Cheng, Suyan,Wang, Lanzhi

, p. 419 - 424 (2015/01/30)

A series of substituted ethyl 4-oxo-4-phenylbut-2-enoates were prepared and reacted with substituted o-phenylenediamine, undergone Michael addition reactions and cyclodehydration to provide novel 4-phenyl-2,3-dihydro-1,5-benzodiazepine-2-carboxylate derivatives with excellent yields. The synthetic protocol fulfilled many green-chemical requirements by using simple catalyst p-toluenesulfonic acid as activator and ethanol as solvent at room temperature.

Structure-activity relationship, cytotoxicity and mode of action of 2-ester-substituted 1,5-benzothiazepines as potent antifungal agents

Kang, Wang,Du, Xingqiong,Wang, Lanzhi,Hu, Lijuan,Dong, Yuhuan,Bian, Yanqing,Li, Yuan

, p. 1305 - 1314 (2013/11/06)

Our studies examined the structural features responsible for the antifungal activity of 2-ethoxycarbonyl-1,5-benzothiazepine (7a). Three series of 1,5-benzothiazepine derivatives were synthesized and screened for their antifungal activity. The results suggested that the ethoxycarbonyl group at the 2 position and the imine moiety on the seven-membered ring are essential for activity. The most potent of the synthesized analogues (7a, 7b) were further studied by evaluating their cytotoxicity and mode of action (for 7a). The results showed that compounds 7a and 7b were relatively safe for BV2 cells, but compound 7a interfered with Cryptococcus neoformans cell wall integrity by increasing the chitinase activity. Therefore, compound 7a was considered safe as an antifungal agent for animal cells. Three series of 1,5-benzothiazepine derivatives were synthesized and their antifungal activities were evaluated to determine the structure-activity relationships with respect to the antifungal activity of 2-ester-substituted 1,5-benzothiazepines. The effective antifungal compounds 7a and 7b were further studied for their antifungal activity, cytotoxicity and mechanism of action (for compound 7a). The results provided important information about this class of benzothiazepines. Copyright

Synthesis and evaluation of anticancer activity of some novel 6-aryl-2-(p-sulfamylphenyl)-pyridazin-3(2H)-ones

Rathish,Javed, Kalim,Ahmad, Shamim,Bano, Sameena,Alam,Akhter, Mymoona,Pillai,Ovais, Syed,Samim, Mohammed

scheme or table, p. 304 - 309 (2012/04/10)

A series of novel pyridazinone derivatives bearing benzenesulfonamide moiety (2a-h) has been synthesized by the condensation of appropriate aroylacrylic acid and 4-hydrazinobenzenesulfonamide hydrochloride in ethanol. Five derivatives (2a, 2b, 2d, 2g and 2h) were evaluated for their anticancer activity toward human cancer cell lines by the National Cancer Institute. The 2h showed remarkable activity against SR (leukemia) and NCI-H522 (non-small cell lung) with a GI50 value of less than 0.1 μM. It also displayed good activity against leukemia (CCRF-CEM, HL-60 (TB), K-562, MOLT-4, RPMI-8226), non-small cell lung cancer (NCI-H460), colon (HCT-116, HCT-15, HT29, KMI2, SW-620), CNS (SF-295), melanoma (MALME-3M, M14, MDA-MB-435 SK-MEL-5), ovarian (OVCAR-3, NCI/ADR-RES) and breast (MCF7) cancer cell lines with a GI 50 less than 1.0 μM. The acute toxicity study of 2h indicated that it is well tolerated intra-peritoneally (400 mg/kg) by athymic nude mice. The 2h may possibly be used as lead compound for developing new anticancer agents.

4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields

Vitorovi?-Todorovi?, Maja D.,Jurani?, Ivan O.,Mandi?, Ljuba M.,Drakuli?, Branko J.

scheme or table, p. 1181 - 1193 (2010/04/06)

Synthesis and anticholinesterase activity of 4-aryl-4-oxo-N-phenyl-2-aminylbutyramides, novel class of reversible, moderately potent cholinesterase inhibitors, are reported. Simple substituent variation on aroyl moiety changes anti-AChE activity for two orders of magnitude; also substitution and type of hetero(ali)cycle in position 2 of butanoic moiety govern AChE/BChE selectivity. The most potent compounds showed mixed-type inhibition, indicating their binding to free enzyme and enzyme-substrate complex. Alignment-independent 3D QSAR study on reported compounds, and compounds having similar potencies obtained from the literature, confirmed that alkyl substitution on aroyl moiety of molecules is requisite for inhibition activity. The presence of hydrophobic moiety at close distance from hydrogen bond acceptor has favorable influence on inhibition potency. Docking studies show that compounds probably bind in the middle of the AChE active site gorge, but are buried deeper inside BChE active site gorge, as a consequence of larger BChE gorge void.

The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction

Jakubec, Pavol,Petras, Pavel,Duris, Andrej,Berkes, Dusan

scheme or table, p. 69 - 74 (2010/04/24)

The novel synthesis of highly enantioenriched N-substituted α-amino-γ-alkyl(aryl)-γ-oxobutanoic acids is described. The process involves the combination of a crystallization-induced asymmetric transformation (CIAT) and the Mannich reaction. The role of retro-Mannich and retro-Michael reactions in the mechanism of the highly stereoselective transformation is also discussed.

Synthesis and analgesic and antiinflammatory activity of 6-phenyl/(4-methylphenyl)-3(2H)-pyridazinon-2-propionamide derivatives

Goekce, Mehtap,Colak, Meral Sirin,Kuepeli, Esra,Sahin, Mustafa Fethi

experimental part, p. 357 - 363 (2010/03/23)

For reducing gastrointestinal toxicity associated with non-steroidal anti-inflammatory drugs (NSAIDs) a variety of 6-phenyl/(4-methylphenyl)-3(2H)- pyridazinon-2-propionamide were synthesized. The structures of these new pyridazinone derivatives were confirmed by their IR, 1 H-NMR spectra and elementary analysis. All the new compounds were tested in vivo for their analgesic and anti-inflammatory activities. The analgesic activity of the test compounds was determined by phenylbenzoquinone-induced writhing assay and the anti-inflammatory activity was evaluated by the carrageenan-induced rat paw edema model. 6-Phenyl-3(2H)-pyridazinon-2-yl-[4-(4-fluorophenyl) piperazinyl] propanamide IV a-3 was the most active one among the synthesized compounds. Also this compound exhibited most potent anti-inflammatory activity. Acetylsalicylic acid and indometacin were used as reference drugs. Adverse effects of the compounds were examined on gastric mucosa. None of the compounds showed gastric ulcerogenic effect compared with the reference NSAIDs. ECV Editio Cantor Verlag.

Syntheses of 1,5-Benzothiazepines: Part II - Synthesis of 4-Aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines

Pant, Umesh C.,Gaur, B. S.,Chugh, Manju

, p. 947 - 950 (2007/10/02)

β-Aroylacrylic acids (II) react with 2-aminothiophenols (I) in ethanol containing gl.acetic acid to give 4-aryl-2-carboxy-2,3-dihydro-1,5-benzothiazepines (VII).Their structures have been established by elemental analyses and spectral data (IR, PMR, 13C NMR and mass).

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