256431-72-8

Basic information

• Product Name: (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile
• Synonyms: (E)-3-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLINYL]-2-PROPENENITRILE;(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propopenenitrile;(2E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enenitrile;(E)-3-(2-Cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)acrylonitrile
• CAS NO: 256431-72-8
• Molecular Formula: C₂₁H₁₅FN₂
• Molecular Weight: 314.36
• EINECS: 1312995-182-4
• Mol File: 256431-72-8.mol

Chemical Properties

• Boiling Point: 494.251 °C at 760 mmHg
• Flash Point: 252.714 °C
• Appearance: white powder
• Density: 1.264
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.686
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.78±0.50(Predicted)
• CAS DataBase Reference: (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile(256431-72-8)
• EPA Substance Registry System: (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile(256431-72-8)

Safety Data

• Hazardous Substances Data: 256431-72-8(Hazardous Substances Data)

Usage

Uses

As of now, there is limited information available in public sources regarding the specific applications of (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile. However, given its complex structure and the presence of bioactive fluorophenyl groups, it can be inferred that this compound may have potential uses in various fields, such as:
Used in Pharmaceutical Industry:
(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile may be used as a pharmaceutical compound for its potential bioactive properties, which could be harnessed for the development of new drugs or therapeutic agents.
Used in Chemical Research:
(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile could be utilized in chemical research as a model or intermediate in the synthesis of other complex molecules, or for studying the properties and reactions of its constituent functional groups.
Used in Material Science:
The unique structure of (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile may also find applications in material science, where its properties could be explored for the development of new materials with specific characteristics, such as optical, electronic, or mechanical properties.

InChI:InChI=1/C21H15FN2/c22-16-11-9-14(10-12-16)20-17-4-1-2-6-19(17)24-21(15-7-8-15)18(20)5-3-13-23/h1-6,9-12,15H,7-8H2/b5-3+

Upstream product

• 3800-06-4 2-amino-4'-fluorobenzophenone 
• 765-43-5 Cyclopropyl methyl ketone 
• 121660-11-5 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline 
• 121660-18-2 [2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinolin-3-yl]-methanol 
• 121660-43-3 2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinoline-3-carbaldehyde 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 121660-37-5 2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline 

Downstream Products

• 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 
• 254452-93-2 (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 
• 254452-91-0 ethyl 5(S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 254452-95-4 ethyl 5(R)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate 
• 380848-30-6 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3S,5S)-dihydroxyhept-6-enic acid ethyl ester 
• 380848-32-8 (E)7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-(3R,5R)-dihydroxyhept-6-enic acid ethyl ester 
• 147511-69-1 (E)-(3S,5S)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 147511-69-1 (E)-(3R,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 254452-90-9 (E)-(S)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid methyl ester 
• 254452-94-3 (E)-(R)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid methyl ester 
• 147526-32-7 pitavastatin 
• 254452-86-3 (E)-(3S,5R)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid 
• 172336-32-2 ethyl (E)-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]hept-6-enoate 
• 172336-32-2 (±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester 

Relevant articles and documents

Diastereoselective synthesis of pitavastatin calcium via bismuth-catalyzed two-component hemiacetal/oxa-Michael addition reaction

An efficient and concise asymmetric synthesis of pitavastatin calcium (1) starting from commercially available (S)-epichlorohydrin is described. A convergent C1 + C6 route allowed for the assembly of the pitavastatin C7 side chain via a Wittig reaction between phosphonium salt 2 and the enantiomerically pure C6-formyl side chain 3. The 1,3-syn-diol acetal motif in 3 was established with excellent stereo control by a diastereoselective bismuth-promoted two-component hemiacetal/oxa-Michael addition reaction of (S)-α,β-unsaturated ketone 4 with acetaldehyde.

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.