(1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one

Base Information

• Chemical Name: (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one
• CAS No.: 148516-16-9
• Molecular Formula: C₂₅H₂₀FNO₃
• Molecular Weight: 401.437

Synonyms:(1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one

Chemical Property of (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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MSDS Files:

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Technology Process of (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one

There total 14 articles about (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one 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: 81.0%

(6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-5,6-dihydro-2H-pyran-2-one (148516-15-8) → (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one (148516-16-9)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol; dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1016/S0957-4166(00)82337-X

Reference yield:

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5) → (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one (148516-16-9)

Guidance literature:

Multi-step reaction with 10 steps

1: tri-n-butylphosphine / pyridine / Ambient temperature

2: 1.) tert-butyllithium / 1.) THF, 2.) THF, -78 deg C, 1 h

3: potassium hydroxide / tetrahydrofuran / 3.5 h / Ambient temperature

4: 100 percent / dimethylsulfoxide / 0.5 h / Ambient temperature

5: 67 percent / palladium(II) chloride, copper(II) chloride, NaOAc / 3 h / 760 Torr / Ambient temperature

6: H₂ / Lindlar cat. / methanol / 25 h / Ambient temperature

7: pyridinium p-toluenesulfonate (PPTS) / toluene / 1.5 h / Heating

8: m-chloroperbenzoic acid (m-CPBA) / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) -40 deg C, 30 min

9: calcium carbonate / toluene / 0.5 h / Heating

10: 81 percent / 30percent hydrogen peroxide, 4 N aq. NaOH / methanol; CH₂Cl₂ / 0.67 h / 0 °C

With potassium hydroxide; sodium hydroxide; tributylphosphine; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium acetate; pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; copper dichloride; palladium dichloride; Lindlar catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0957-4166(00)82337-X

Reference yield:

2-cyclopropyl-4-(4-fluoro-phenyl)-3-quinoline carboxylic acid ethyl ester (148516-11-4) → (1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one (148516-16-9)

Guidance literature:

Multi-step reaction with 11 steps

1: lithium aluminum hydride / tetrahydrofuran / from 0 deg C to RT

2: tri-n-butylphosphine / pyridine / Ambient temperature

3: 1.) tert-butyllithium / 1.) THF, 2.) THF, -78 deg C, 1 h

4: potassium hydroxide / tetrahydrofuran / 3.5 h / Ambient temperature

5: 100 percent / dimethylsulfoxide / 0.5 h / Ambient temperature

6: 67 percent / palladium(II) chloride, copper(II) chloride, NaOAc / 3 h / 760 Torr / Ambient temperature

7: H₂ / Lindlar cat. / methanol / 25 h / Ambient temperature

8: pyridinium p-toluenesulfonate (PPTS) / toluene / 1.5 h / Heating

9: m-chloroperbenzoic acid (m-CPBA) / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) -40 deg C, 30 min

10: calcium carbonate / toluene / 0.5 h / Heating

11: 81 percent / 30percent hydrogen peroxide, 4 N aq. NaOH / methanol; CH₂Cl₂ / 0.67 h / 0 °C

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; tributylphosphine; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium acetate; pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; copper dichloride; palladium dichloride; Lindlar catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0957-4166(00)82337-X

upstream raw materials:

(6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-5,6-dihydro-2H-pyran-2-one

(S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne

(S)-2-(3-trimethylsilyl-2-propynyl)oxirane

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

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