(R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate

Base Information

• Chemical Name: (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate
• CAS No.: 1327274-55-4
• Molecular Formula: C₂₂H₁₉NO₄
• Molecular Weight: 361.397
• Mol file: 1327274-55-4.mol

Synonyms:(R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate

Chemical Property of (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate

There total 3 articles about (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

quinoline 2-carbaldehyde (5470-96-2) + (E)-ethyl-2-oxo-4-phenylbut-3-enoate (17451-20-6,55674-14-1,55629-96-4) → (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate (1327274-55-4)

Guidance literature:

(E)-ethyl-2-oxo-4-phenylbut-3-enoate; With (5R,7R)-7-fluoro-5-isopropyl-2-(perfluorophenyl)-6,7-dihydro-5H-pyrrolo[2,1c][1,2,4]triazol-2-ium tetrafluoroborate; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

quinoline 2-carbaldehyde; With N-ethyl-N,N-diisopropylamine; In dichloromethane; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol202040b

Reference yield:

(E)-2-oxo-4-phenyl-3-butenoic acid (1914-59-6) → (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate (1327274-55-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / water; toluene / 4 h / 95 °C / Inert atmosphere

2.1: (5R,7R)-7-fluoro-5-isopropyl-2-(perfluorophenyl)-6,7-dihydro-5H-pyrrolo[2,1c][1,2,4]triazol-2-ium tetrafluoroborate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

2.2: Inert atmosphere

With hydrogenchloride; (5R,7R)-7-fluoro-5-isopropyl-2-(perfluorophenyl)-6,7-dihydro-5H-pyrrolo[2,1c][1,2,4]triazol-2-ium tetrafluoroborate; In dichloromethane; water; toluene; 2.1: Stetter reaction / 2.2: Stetter reaction;

DOI:10.1021/ol202040b

Reference yield:

benzaldehyde (100-52-7) → (R)-ethyl 2,5-dioxo-4-phenyl-5-(quinolin-2-yl)pentanoate (1327274-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanol; water / 0.17 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

1.3: pH 2 / Inert atmosphere

2.1: hydrogenchloride / water; toluene / 4 h / 95 °C / Inert atmosphere

3.1: (5R,7R)-7-fluoro-5-isopropyl-2-(perfluorophenyl)-6,7-dihydro-5H-pyrrolo[2,1c][1,2,4]triazol-2-ium tetrafluoroborate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

With hydrogenchloride; (5R,7R)-7-fluoro-5-isopropyl-2-(perfluorophenyl)-6,7-dihydro-5H-pyrrolo[2,1c][1,2,4]triazol-2-ium tetrafluoroborate; In methanol; dichloromethane; water; toluene; 3.1: Stetter reaction / 3.2: Stetter reaction;

DOI:10.1021/ol202040b

upstream raw materials:

quinoline 2-carbaldehyde

(E)-ethyl-2-oxo-4-phenylbut-3-enoate

(E)-2-oxo-4-phenyl-3-butenoic acid

benzaldehyde