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Cas Database

157019-58-4

157019-58-4

Identification

  • Product Name:2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

  • CAS Number: 157019-58-4

  • EINECS:

  • Molecular Weight:366.049

  • Molecular Formula: C12H14Br2O3

  • HS Code:

  • Mol File:157019-58-4.mol

Synonyms:2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

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Relevant articles and documentsAll total 5 Articles be found

Transmission of substituent effects through extended systems-III. p-Substituted ethyl trans cinnamates and phenylpropiolates

Butt, G.,Topsom, R. D.

, p. 649 - 654 (1982)

Infrared data and 13C chemical shifts are reported for a series of ethyl p-substituted trans-cinnamates and ethyl phenylpropiolates.The i.r. values include intensities for the benzene, ethylene and carbonyl vibrations which allow an estimation of resonance effects.The relative importance of the various mechanisms of transmission of substituent effects are discussed and compared to those previously reported for p-substituted trans cinnamonitriles.It is shown that the carbon-carbon triple bond is less efficient in transmitting substituent effects than carbon-carbon double bonds.

Synthesis and biological evaluation of 4-arylcoumarins as potential anti-Alzheimer's disease agents

Miao, Yuhang,Sun, Jie,Wang, Xiaojing,Yang, Jie,Yun, Yinling

, (2020/01/03)

Alzheimer's disease (AD) is a progressive neurological degenerative disease that has complex pathogenesis. A variety of studies in humans indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted 4-arylcoumarin derivatives were synthesised, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity, MAO inhibitory activity, and antioxidant activity. Most of the compounds were found to exhibit high inhibitory activity, and individual compounds have extremely excellent activities. Therefore 4-arylcoumarins provides an idea for drugs design for the development of therapeutic or preventive agents for AD.

Preparation method of neoflavonoids

-

, (2017/04/26)

The invention relates to the field of chemical synthesis, in particular to a preparation method of neoflavonoids. The preparation method is characterized by comprising the following steps of using substituted benzaldehyde as an initial raw material to be reacted with malonic acid to generate a substituted phenylacrylic acid compound; performing an addition reaction, an elimination reaction and the like on the substituted phenylacrylic acid compound, or performing acetylation so as to protect a phenolic hydroxyl group, then performing a bromination reaction and the elimination reaction so as to synthesize the substituted phenylpropiolic acid compound ; and using montmorillonite K-10 after being acidulated by sulfuric acid as a catalyst, enabling the substituted phenylpropiolic acid compound and a phenolic compound to perform a heating reaction so as to generate the neoflavonoids. Compared with the prior art, the preparation method of the neoflavonoids, disclosed by the invention, has the characteristics that raw materials are cheap, and easy to obtain, the operation is simple, the catalyst can be recovered for use, and the method is environmentally-friendly, the post-treatment is simple, and the production cost is low, and the method has a high popularization and application value.

An efficient synthesis of neoflavonoid antioxidants based on Montmorillonite K-10 catalysis

Lee,Tseng,Lee

, p. 2247 - 2254 (2007/10/03)

A new approach to synthesis of neoflavonoids, based on a high yielding Montmorillonite K-10 catalyzed lactone ring forming cyclization process, is described. The utility of this methodology is exemplified by its employment in the preparation of the substituted 4-phenylneoflavonoids 1-8. The free radical scavenging properties of these substances were evaluated. The neoflavonoids 1 and 5, which mimic esculetin-type antioxidants, were observed to quench hydrazyl free radicals.

Enantioselective Catalytic Epoxidation of Cinnamate Esters

Jacobsen, Eric N.,Deng, Li,Furukawa, Yoshiro,Martinez, Luis E.

, p. 4323 - 4334 (2007/10/02)

A broad study of the (salen)Mn(III)-catalyzed asymmetric epoxidation of cis-cinnamate esters reveals that the steric properties of the ester group have a profound influence on enantioselectivity in the epoxidation reaction, with bulkier esters affording highest ee's.The sensitivity of the reaction selectivity to the steric properties of the cis-alkene are consistent with a "skewed" side-on approach of olefin to the metal -oxo.The electronic properties of the substrate arene ring substituents do not correlate with epoxidation ee, but instead with the cis/trans partitioning of product formation.Evidence is provided for a non-polar inter mediate in a stepwise oxygen-atom-transfer mechanism.The presence of pyridine N-oxide derivatives has a significant effect on catalysts rates and total turnovers, but negligible influence on the stereoselectivity of epoxidation.A mechanistic basis for the role of these additives is proposed.The synthetic applicability of the cinnamate epoxidation methodology is illustrated in the highly enantioslective synthesis of diltiazem.

Process route upstream and downstream products

Process route

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

Conditions
Conditions Yield
With bromine;
99%
With bromine; In tetrachloromethane; Heating;
With bromine; In dichloromethane; at 0 ℃;
ethyl 3-(4-methoxyphenyl)propynoate
51718-85-5

ethyl 3-(4-methoxyphenyl)propynoate

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 2.3 percent Chromat. / quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature
2: 99 percent / Br2
With quinoline; hydrogen; bromine; Lindlar's catalyst; In hexane;
3-(4'-methoxyphenyl)propenoic acid
830-09-1

3-(4'-methoxyphenyl)propenoic acid

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: thionyl chloride / 2 h / 82 °C
2: bromine / dichloromethane / 1.5 h / Cooling with ice
With thionyl chloride; bromine; In dichloromethane;
Multi-step reaction with 2 steps
1: thionyl chloride
2: bromine / dichloromethane / 0.33 h / 0 °C
With thionyl chloride; bromine; In dichloromethane;
(E)-3-(4-methoxyphenyl)acrylic acid
943-89-5

(E)-3-(4-methoxyphenyl)acrylic acid

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: SOCl2 / 4 h / Heating
2: Br2 / CH2Cl2 / 0 °C
With thionyl chloride; bromine; In dichloromethane;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium
2: diethyl ether; bromine
With diethyl ether; bromine; sodium;
2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

p-methoxycinnamic acid isopropyl ester
53484-51-8,5466-76-2

p-methoxycinnamic acid isopropyl ester

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 51 percent / KOH / aq. ethanol / 12 h / Heating
2: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
3: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature
With quinoline; dmap; potassium hydroxide; hydrogen; dicyclohexyl-carbodiimide; Lindlar's catalyst; In ethanol; hexane; dichloromethane;
2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
42399-49-5

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Conditions
Conditions Yield
Multi-step reaction with 8 steps
1: 51 percent / KOH / aq. ethanol / 12 h / Heating
2: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
3: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature
4: 55 percent / 1,2-dichloro-ethane / 24 h / Irradiation
5: 4-picoline-N-oxide, sodium hypochlorite / (salen)Mn(III)-complex / benzene; H2O / 24 h / 4 °C
6: 1.) NaHCO3, 2.) FeSO4.7H2O / 1.) EtOH, reflux, 12 h; 2.) EtOH, water, reflux, 30 min
7: 56 percent / NaOH / H2O; ethanol / 1 h / Heating
8: 64 percent / xylene / 12 h / Heating
With 4-methylpyridine-1-oxide; quinoline; dmap; potassium hydroxide; sodium hydroxide; sodium hypochlorite; hydrogen; sodium hydrogencarbonate; iron(II) sulfate; dicyclohexyl-carbodiimide; Lindlar's catalyst; In ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; xylene; benzene;
Multi-step reaction with 7 steps
1: 51 percent / KOH / aq. ethanol / 12 h / Heating
2: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
3: 93 percent Chromat. / quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature
4: 4-picoline-N-oxide, sodium hypochlorite / (salen)Mn(III)-complex / benzene; H2O / 24 h / 4 °C
5: 1.) NaHCO3, 2.) FeSO4.7H2O / 1.) EtOH, reflux, 12 h; 2.) EtOH, water, reflux, 30 min
6: 56 percent / NaOH / H2O; ethanol / 1 h / Heating
7: 64 percent / xylene / 12 h / Heating
With 4-methylpyridine-1-oxide; quinoline; dmap; potassium hydroxide; sodium hydroxide; sodium hypochlorite; hydrogen; sodium hydrogencarbonate; iron(II) sulfate; dicyclohexyl-carbodiimide; Lindlar's catalyst; In ethanol; hexane; dichloromethane; water; xylene; benzene;
ethanol
64-17-5

ethanol

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

<i>N</i>,<i>N</i>-dimethyl-aniline
121-69-7,77733-26-7

N,N-dimethyl-aniline

ethyl p-methoxycinnamate
24393-56-4,51507-22-3,1929-30-2

ethyl p-methoxycinnamate

ethyl 3-(4-methoxyphenyl)propynoate
51718-85-5

ethyl 3-(4-methoxyphenyl)propynoate

Conditions
Conditions Yield
2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid
42399-48-4

(2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 51 percent / KOH / aq. ethanol / 12 h / Heating
2: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
3: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature
4: 55 percent / 1,2-dichloro-ethane / 24 h / Irradiation
5: 4-picoline-N-oxide, sodium hypochlorite / (salen)Mn(III)-complex / benzene; H2O / 24 h / 4 °C
6: 1.) NaHCO3, 2.) FeSO4.7H2O / 1.) EtOH, reflux, 12 h; 2.) EtOH, water, reflux, 30 min
7: 56 percent / NaOH / H2O; ethanol / 1 h / Heating
With 4-methylpyridine-1-oxide; quinoline; dmap; potassium hydroxide; sodium hydroxide; sodium hypochlorite; hydrogen; sodium hydrogencarbonate; iron(II) sulfate; dicyclohexyl-carbodiimide; Lindlar's catalyst; In ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; benzene;
Multi-step reaction with 6 steps
1: 51 percent / KOH / aq. ethanol / 12 h / Heating
2: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature
3: 93 percent Chromat. / quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature
4: 4-picoline-N-oxide, sodium hypochlorite / (salen)Mn(III)-complex / benzene; H2O / 24 h / 4 °C
5: 1.) NaHCO3, 2.) FeSO4.7H2O / 1.) EtOH, reflux, 12 h; 2.) EtOH, water, reflux, 30 min
6: 56 percent / NaOH / H2O; ethanol / 1 h / Heating
With 4-methylpyridine-1-oxide; quinoline; dmap; potassium hydroxide; sodium hydroxide; sodium hypochlorite; hydrogen; sodium hydrogencarbonate; iron(II) sulfate; dicyclohexyl-carbodiimide; Lindlar's catalyst; In ethanol; hexane; dichloromethane; water; benzene;
2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester
157019-58-4

2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester

3-(4-methoxyphenyl)propynoic acid
2227-57-8

3-(4-methoxyphenyl)propynoic acid

Conditions
Conditions Yield
With potassium hydroxide; In ethanol; Reflux;
65%
With potassium hydroxide; In ethanol; for 12h; Heating;
51%
With potassium hydroxide; In ethanol; for 4h; Heating;
With ethanol; potassium hydroxide; at 82 ℃; for 10h;
4.6 g
With potassium hydroxide; In ethanol; for 6h; Reflux;

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