121660-63-7

Basic information

• Product Name: (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN
• Synonyms: (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN
• CAS NO: 121660-63-7
• Molecular Formula: C21H16FNO
• Molecular Weight: 317.3562432
• Mol File: 121660-63-7.mol

Chemical Properties

• Boiling Point: 491.793 °C at 760 mmHg
• Flash Point: 251.228 °C
• Appearance: /
• Density: 1.257 g/cm³
• CAS DataBase Reference: (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN(121660-63-7)
• EPA Substance Registry System: (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN(121660-63-7)

Safety Data

• Hazardous Substances Data: 121660-63-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN is used as a valuable precursor in the synthesis of various organic compounds due to its reactivity and the presence of a double bond in the acrolein group, which makes it prone to undergo addition reactions.
Used in Pharmaceutical Research:
In the Pharmaceutical Industry, (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN may be utilized as a starting material or intermediate in the development of new drugs, given its unique structure and potential biological activity. The substitution pattern on the quinolyl and fluorophenyl groups could be explored for designing compounds with specific pharmacological properties.
Used in Materials Science:
(E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLYL]-ACROLEIN could be employed in the development of new materials with unique properties, such as polymers or other advanced materials, owing to its reactive acrolein group and the possibility of forming various chemical bonds and structures.

Upstream product

• 256431-72-8 (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile 
• 391681-95-1 2-cyclopropyl-3-(3-ethoxy-1-hydroxy-2-propenyl)-4-(4-fluorophenyl)quinoline 
• 3800-06-4 2-amino-4'-fluorobenzophenone 
• 32249-35-7 methyl 3-cyclopropyl-3-oxopropanoate 
• 121660-11-5 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 
• 121659-86-7 methyl 4-(4'-fluorophenyl)-2-cyclopropylquinoline-3-carboxylate 
• 121660-43-3 2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinoline-3-carbaldehyde 
• 121660-18-2 [2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinolin-3-yl]-methanol 
• 113832-57-8 N-ethylidenecyclohexylamine 
• 7020-80-6 acetaldehyde N-tert-butylimine 
• 6898-74-4 Acetaldehyd-butylimin 
• 1403338-19-1 methyl (2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]acrylate 

Downstream Products

• 254452-93-2 (E)-(R)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid (R)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 254452-89-6 (E)-(S)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester 
• 254452-86-3 (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 254452-94-3 (E)-(R)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid methyl ester 
• 254452-90-9 (E)-(S)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid methyl ester 
• 147511-69-1 (E)-(3R,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 147511-69-1 (E)-(3S,5S)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 380848-32-8 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3R,5R)-dihydroxyhept-6-enic acid ethyl ester 
• 380848-30-6 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3S,5S)-dihydroxyhept-6-enic acid ethyl ester 
• 254452-95-4 ethyl 5(R)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 1403338-21-5 (3S,4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxypentenoic acid (R)-α-methylbenzylamine salt 
• 1403338-23-7 C₃₂H₃₆FN₃O₂Si 
• 222306-19-6 (3S,4E)-5-[2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl]-3-hydroxypentenoic acid 
• 1403338-27-1 C₂₉H₃₄FNO₃Si 

Relevant articles and documents

Synthesis method of (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein

The invention relates to a synthesis technology of pharmaceutical chemicals and particularly relates to a synthesis technology of (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein. (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-2-ethyl acrylate is taken as a raw material, and is thoroughly reduced into allyl alcohol through hydroboron, (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein is synthesized through DMSO oxidation, reaction conditions are optimized, and the yield of the (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein reaches over 95%. The method is simple in operation step, short in reaction period and high in conversion ratio; the required equipment is simple; the method is suitable for industrial massive production; the content of the produced (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein is greater than 99%; and the technical requirements of the market on the (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinoline]-2-acrolein are met.

PROCESS FOR PREPARING QUINOLINE DERIVATIVE

The present invention relates to a novel process for preparing Pitavastatin calcium salt of formula (I).

PROCESS FOR PRODUCING QUINOLINE COMPOUND

By a production method of a quinoline compound represented by the formula (I), which comprises reacting quinolinecarbaldehyde represented by the formula (II) with an imine compound represented by the formula (III) and then subjecting the resulting compoun

PROCESS FOR PREPARING QUINOLYLACRYLONITRILE AND INTERMEDIATES THEREFOR

3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrite is prepared by reacting 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde with acetonitrile in the presence of a base and then adding a dehydrating to the reaction mixture to conduct

PROCESS FOR THE PREPARATION OF QUINOLYLPROPENAL

3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enal is prepared in a high yield by reducing 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrite with Raney nickel either in the presence of formic acid and 0.25 to 1 part by volume of water per part by volume of formic acid or in the presence of both an amine salt of formic acid and an organic acid.

Process for the preparation of quinoline derivative and intermediate therefor

The present invention relates a process for producing the quinoline derivative (3) via the nitrile compound (1) obtained by reacting the aldehyde compound represented by formula (2) with diethyl cyanomethylphosphonate and its intermediate (1).

Synthesis and biological evaluations of quinoline-based HMG-CoA reductase inhibitors

A series of quinoline-based 3,5-dihydroxyheptenoic acid derivatives were synthesized from quinolinecarboxylic acid esters by homologation, aldol condensation with ethyl acetoacetate dianion, and reduction of 3-hydroxyketone to evaluate their ability to inhibit the enzyme HMG-CoA reductase in vitro. In agreement with previous literature, a strict structural requirement exists on the external ring, and 4-fluorophenyl is the most active in this system. For the central ring, substitution on positions 6, 7, and 8 of the central quinoline nucleus moderately affected the potency, whereas the alkyl side chain on the 2-position had a more pronounced influence on activity. Among the derivatives, NK-104 (pitavastatin calcium), which has a cyclopropyl group as the alkyl side chain, showed the greatest potency. We found that further modulation and improvement in potency at inhibiting HMG-CoA reductase was obtained by having the optimal substituents flanking the desmethylmevalonic acid portion, that is, 4-fluorophenyl and cyclopropyl, instead of the usual isopropyl group.

First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104

First systematic chiral syntheses of two pairs of enantiomers with 3,5-dihydroxyheptenoic acid chain, associated with a potent synthetic statin NK-104 are reported. A pair of syn diol isomers (NK-104 and its enantiomer) was obtained efficiently by diastereomeric resolution. The synthesis of a pair of anti diol isomers (3-epimer and 5-epimer) was accomplished effectively by the asymmetric aldol reaction followed by anti stereoselective reduction as key steps. Their purity determinations were effected by chiral HPLC analysis.