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Cas Database

79137-48-7

79137-48-7

Identification

Synonyms:5(4H)-Oxazolone, 2-(4-methoxyphenyl)-4-(1-methylethyl)-

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 6 Articles be found

Asymmetric trifluoromethylthiolation of azlactones under chiral phase transfer catalysis

Alemán, José,Bernardi, Luca,Borello, Fabio,Cano, Rafael,Capaccio, Vito,Díaz-Tendero, Sergio,De Riccardis, Francesco,Della Sala, Giorgio,Rodríguez, Ricardo I.,Sicignano, Marina

, p. 2914 - 2920 (2020/04/28)

The first enantioselective method for the installation of the SCF3 group at the C-4 position of azlactones is described in the present communication under quinidinium phase transfer catalysis. The higher performance of substrates containing electron-rich 2-aryl groups at the azlactone was rationalized using DFT calculations.

Catalytic Aerobic Cross-Dehydrogenative Coupling of Azlactones en Route to α,α-Disubstituted α-Amino Acids

Tsuji, Taro,Tanaka, Takafumi,Tanaka, Tsukushi,Yazaki, Ryo,Ohshima, Takashi

, p. 4164 - 4170 (2020/06/04)

We developed a catalytic aerobic method to synthesize α,α-disubstituted α-amino acids through cross-dehydrogenative coupling of azlactones. Combining an iron catalyst with a bisoxazolidine ligand resulted in high catalytic performance, and cross-coupling with an indole proceeded smoothly under aerobic conditions. A wide variety of α-aryl and aliphatic amino acid derived azlactones were applied to the present catalysis. In addition, a quaternary carbon could be constructed using oxindole and benzofuranone under aerobic conditions.

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

Deng, Yun,Guo, Hai-Ming,Huang, Bin,Li, Ning,Qu, Gui-Rong,Tian, Yin,Wu, Xiao-Xia,Xie, Ming-Sheng

supporting information, p. 19226 - 19238 (2020/11/13)

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.

Strategy for Catalytic Chemoselective Cross-Enolate Coupling Reaction via a Transient Homocoupling Dimer

Tanaka, Takafumi,Tanaka, Tsukushi,Tsuji, Taro,Yazaki, Ryo,Ohshima, Takashi

supporting information, p. 3541 - 3544 (2018/06/26)

A new strategy, a transient homocoupling dimer strategy, for direct catalytic oxidative cross-enolate coupling reactions is developed. Cross-enolate coupling products bearing a (contiguous) tetrasubstituted carbon center were obtained chemoselectively without the need for stoichiometric amounts of strong bases/metal oxidants, and thus, the present catalysis provides a general method for the synthesis of unnatural α,α-disubstituted amino acid motifs. The distinct transformation of azlactone and 2-acylimidazole units highlighted the synthetic utility of the present catalysis.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Wang, Tianli,Yu, Zhaoyuan,Hoon, Ding Long,Phee, Claire Yan,Lan, Yu,Lu, Yixin

supporting information, p. 265 - 271 (2016/01/25)

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Process route upstream and downstream products

Process route

(4-methoxybenzoyl)valine
93709-65-0

(4-methoxybenzoyl)valine

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

Conditions
Conditions Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;
78%
With acetic anhydride;
With dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;
906 mg
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; Inert atmosphere;
2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: thionyl chloride / 0 °C / Reflux
2: triethylamine / dichloromethane / 0 - 20 °C
3: sodium hydroxide / methanol
4: dicyclohexyl-carbodiimide / dichloromethane / 20 °C
With thionyl chloride; triethylamine; dicyclohexyl-carbodiimide; sodium hydroxide; In methanol; dichloromethane;
Multi-step reaction with 2 steps
1: sodium hydroxide / 2 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C / Inert atmosphere
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In dichloromethane;
Multi-step reaction with 2 steps
1: sodium carbonate / 1,4-dioxane; water / 1 h / 0 - 20 °C / Inert atmosphere
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
With sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water;
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium hydroxide / 2 h / 20 °C
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 20 °C / Inert atmosphere
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In dichloromethane;
Multi-step reaction with 2 steps
1: sodium carbonate / 1,4-dioxane; water / 1 h / 0 - 20 °C / Inert atmosphere
2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
With sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water;
DL-valine methyl ester hydrochloride
5619-05-6,6306-52-1,7146-15-8

DL-valine methyl ester hydrochloride

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: sodium hydroxide / methanol
3: dicyclohexyl-carbodiimide / dichloromethane / 20 °C
With triethylamine; dicyclohexyl-carbodiimide; sodium hydroxide; In methanol; dichloromethane;
C<sub>14</sub>H<sub>19</sub>NO<sub>4</sub>
251538-67-7

C14H19NO4

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol
2: dicyclohexyl-carbodiimide / dichloromethane / 20 °C
With dicyclohexyl-carbodiimide; sodium hydroxide; In methanol; dichloromethane;
4-methoxyphenylchloroformate
7693-41-6

4-methoxyphenylchloroformate

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

4-methoxyphenyl 2-(4-methoxyphenyl)-4-isopropyloxazol-5-yl carbonate
1203507-22-5

4-methoxyphenyl 2-(4-methoxyphenyl)-4-isopropyloxazol-5-yl carbonate

Conditions
Conditions Yield
With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;
80%
methanol
67-56-1

methanol

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

(S)-methyl 2-(4-methoxybenzamido)-4-methylpentanoate

(S)-methyl 2-(4-methoxybenzamido)-4-methylpentanoate

Conditions
Conditions Yield
With (S)-2-(2-((2,6-diisopropylphenyl)carbamoyl)pyrrolidin-1-yl)-4-(pyrrolidin-1-yl)pyridine 1-oxide; benzoic acid; In dichloromethane; at 20 ℃; for 72h; enantioselective reaction; Resolution of racemate;
84%
2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

methyl chloroformate
79-22-1

methyl chloroformate

2-(4-methoxyphenyl)-4-iso-propyloxazol-5-yl methyl carbonate
909122-68-5

2-(4-methoxyphenyl)-4-iso-propyloxazol-5-yl methyl carbonate

Conditions
Conditions Yield
With triethylamine; In tetrahydrofuran; at 0 - 25 ℃;
89%
With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;
89%
2,6-di-tert-butyl-4-(4-methoxybenzylidene)-cyclohexa-2,5-dienone
71711-98-3

2,6-di-tert-butyl-4-(4-methoxybenzylidene)-cyclohexa-2,5-dienone

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

(R)-4-((S)-(3,5-di-tert-butyl-4-hydroxyphenyl)(4-methoxyphenyl)methyl)-2-(4-methoxyphenyl)-4-propyloxazol-5(4H)-one

(R)-4-((S)-(3,5-di-tert-butyl-4-hydroxyphenyl)(4-methoxyphenyl)methyl)-2-(4-methoxyphenyl)-4-propyloxazol-5(4H)-one

Conditions
Conditions Yield
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In tetrachloromethane; at 50 ℃; for 48h; stereoselective reaction;
82%
2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole
79137-48-7

2-(4-methoxyphenyl)-5-oxo-4-iso-propyl-4,5-dihydrooxazole

4-benzylidene-2-phenylisoxazolidine-3,5-dione
5289-18-9

4-benzylidene-2-phenylisoxazolidine-3,5-dione

2-isopropyl-N,4-diphenyl-5-(p-methoxyphenyl)-1H-pyrrole-3-carboxamide

2-isopropyl-N,4-diphenyl-5-(p-methoxyphenyl)-1H-pyrrole-3-carboxamide

Conditions
Conditions Yield
With potassium acetate; In 1,2-dichloro-ethane; at 75 ℃; for 10h; regioselective reaction; Schlenk technique;
83%

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