10541-56-7

Usage

Uses

Used in Pharmaceutical Industry:
4'-N-OCTYLACETOPHENONE is used as an intermediate in the synthesis of Diethyl 2-Acetamido-2-[2-(4-octylphenyl)-2-oxo-ethyl]malonate (D443140) for its role in the preparation of the immunosuppressive agent FRY-720 (F805000). This application is significant as it contributes to the development of pharmaceuticals that can help regulate the immune system and potentially treat conditions related to immune system dysregulation.

InChI:InChI=1/C16H24O/c1-3-4-5-6-7-8-9-15-10-12-16(13-11-15)14(2)17/h10-13H,3-9H2,1-2H3

Upstream product

• 2189-60-8 Octylbenzene 
• 75-36-5 acetyl chloride 
• 28741-08-4 n-octylboronic acid 
• 99-90-1 para-bromoacetophenone 
• 108-24-7 acetic anhydride 
• 111-85-3 n-chlorooctane 
• 149104-90-5 4-acetylphenylboronic acid 
• 2550-26-7 4-Phenyl-2-butanone 
• 133997-05-4 (4-octylphenyl)boronic acid 
• 872-05-9 1-Decene 
• 14850-23-8 trans-4-Octene 
• 13329-40-3 4-Iodoacetophenone 
• 629-27-6 1-Iodooctane 
• 1674-37-9 n-octanophenone 

Downstream Products

• 173031-24-8 ethyl 3-oxo-3-(4-octyl)propionate 
• 78575-34-5 [(E)-Hydroxyimino]-(4-octyl-phenyl)-acetaldehyde oxime 
• 1233091-81-0 5-(4-octylphenyl)-1,3,4-thiadiazol-2-amine 
• 1369885-79-9 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl-N-(5-(4-octylphenyl)-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamide 
• 3575-31-3 4-octylbenzoic acid 
• 268557-49-9 2-(acetylamino)-2-[2-(4-octylphenyl)-2-oxo-ethyl]propanedioic acid diethyl ester 
• 1620230-20-7 N-[1,1-bis(hydroxymethyl)-3chloro-(4-octylphenyl)propyl]acetamide 
• 249289-10-9 N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl) butan-2-yl) acetamide 
• 162359-55-9 fingolimod 
• 1620230-21-8 N-[1,1-bis(hydroxymethyl)-3-(4-octylphenyl)allyl]acetamide 
• 1620230-22-9 2-amino-2-[2-(4-octylphenyl)vinyl]propane-1,3-diol 
• 93-58-3 benzoic acid methyl ester 

Relevant academic research and scientific papers

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation

A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.

Terminal-Selective C(sp3)-H Arylation: NiH-Catalyzed Remote Hydroarylation of Unactivated Internal Olefins

A terminal-selective migratory hydroarylation of unactivated olefins has been developed though a NiH-catalyzed alkene isomerization-hydroarylation relay process. This sp3C-H arylation was achieved with a simple pyrox ligand under mild conditions. The practicality and synthetic flexibility of the method is highlighted by the successful regioconvergent conversion of isomeric mixtures of alkenes to value-added linear arylation products on a gram scale.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation

A combinatorial nickel-catalyzed monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides by reductive cross-coupling has been developed. This method demonstrated high efficiency, mild conditions, and excellent functional-group tolerance, thus enabling the late-stage monofluoroalkylation of diverse drugs. The key to success was the combination of diverse readily available bidentate and monodentate pyridine-type nitrogen ligands with nickel, which in situ generated a variety of readily tunable catalysts to promote fluoroalkylation with broad scope with respect to both coupling partners. This combinatorial catalysis strategy offers a solution for nickel-catalyzed reductive cross-coupling reactions and provides an efficient way to synthesize fluoroalkylated druglike molecules for drug discovery.

INTERMEDIATES AND PROCESS FOR THE PREPARATION OF HIGH PURITY FINGOLIMOD HYDROCHLORIDE

The present invention relates to a simple and commercially feasible preparation of Fingolimod hydrochloride with high purity of greater than 99.9%. The.present invention also provides novel intermediates for the preparation of Fingolimod Hydrochloride of Formula 1.

Synthesis, insecticidal evaluation of novel 1,3,4-thiadiazole chrysanthemamide derivatives formed by an EDCI/HOBt condensation

A series of novel pesticides with two components derived from a 1,3,4-thiadiazole and chrysanthemic acid were synthesised via an EDCI/HOBt condensation. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, 1H NMR and elemental analyses. Their insecticidal activity was also evaluated.

Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides

(Chemical Equation Presented) The direct reductive cross-coupling of alkyl halides with aryl halides is described. The transformation is efficient (equimolar amounts of the starting materials are used), generally high-yielding (all but one between 55 and 88% yield), highly functional-group-tolerant [OH, NHBoc, NHCbz, Bpin, C(O)Me, CO2Et, and CN are all tolerated], and easy to perform (uses only benchtop-stable reagents, tolerates small amounts of water and oxygen, changes color when complete, and uses filtration workup). The reaction appears to avoid the formation of intermediate organomanganese species, and a synergistic effect was found when a mixture of two ligands was employed.

Syndiospecific synthesis of longer p-n-alkyl-substituted polystyrenes using monocyclopentadienyl-type titanium catalysts

Substituted styrenes with linear alkyl substituents (C6 to C12) at the para position on the ring were synthesized and polymerized using the (Me)5CpTi(OMe)3/MAO catalytic system. Increased polymerization activiti

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids

Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.

Method for producing Suzuki coupling compound catalysed by a nickel compound

There are disclosed a method for producing a cross-coupling compound of formula (3):(Y-)(n-1)R1-R2-(R1)(n'-L) ???wherein R1 represents ???a substituted or unsubstituted, linear, branched, or cyclic hydrocarbon group, and ???n and n' each represent 1 or 2, ???provided that when n and n' are the same, both n and n' are not 2, ???R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group, ???and ???Y represents R2 or X1, wherein R2 is as defined above, and X1 represents a chlorine, bromine or iodine atom, ???which method comprises reacting ???an organic halide of formula (1):n'(R1X1?n), ???wherein R1 is as defined above and carbon atoms at the α and β positions relative to X1 are sp3 carbon atoms, and X1, n and n' are as defined above, ???with a boron compound of formula (2):m{R2(BX2?2)n'}, ???wherein R2 and n' are as defined above, ???X2 independently represents a hydroxyl group or an alkoxy or aryloxy group, or X22 together form an alkoxy or aryloxy group, and m represents 1 or 2, and m≤n, and the boron atom is bonded with an sp2 carbon atom of R2 group, or a boronic acid trimer anhydride thereof, in the presence of a base and a catalyst comprising a nickel compound and a compound of formula (i): ???wherein R3 represents a substituted or unsubstituted alkyl group, ???R4 represents a hydrogen atom or a substituted or unsubstituted alkyl group, ???1 represents an integer of 1 to 3, and ???p and q each represents an integer of 0 to 2; and a catalyst.