19019-21-7

Usage

Derivative of

Acetophenone

Uses

Production of pharmaceuticals, perfumes, flavorings, and as an intermediate in the synthesis of various organic compounds

Physical properties

Clear, colorless liquid with a sweet, floral odor

Safety precautions

Flammable, should be handled and stored with proper safety measures in place

InChI:InChI=1/C11H14O2/c1-8(2)7-11(13)9-5-3-4-6-10(9)12/h3-6,8,12H,7H2,1-2H3

Upstream product

• 108-12-3 isopentanoyl chloride 
• 108-95-2 phenol 
• 15806-38-9 phenyl 3-methylbutanoate 
• 503-74-2 3-methylbutyric acid 
• 611-20-1 salicylonitrile 
• 78-77-3 Isobutyl bromide 
• 926-62-5 isobutylmagnesium bromide 
• 19311-91-2 N,N-diethylsalicylamide 
• 81851-76-5 (2-methylpropyl)diphenylchlorosilane 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 95255-51-9 (-)-2-{1-{[(1R)-1-phenylethyl]imino}ethyl}phenol 
• 89-95-2 2-methyl-benzyl alcohol 
• 193687-89-7 2-(1-hydroxy-3-methyl-butyl)phenol 
• 3780-33-4 2,3-dihydro-2,2-dimethylbenzo[b]pyran-4-one 

Downstream Products

• 115291-70-8 (2-isovaleryl-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 5032-03-1 (3-methyl-butyl)-phenol 
• 56014-87-0 (Z)-3-(2-methylpropylidene)phthalide 
• 364045-13-6 (4R)-4-isobutyl-3-[(1R)-1-phenylethyl]-3,4-dihydro-2H-1,3-benzoxazine 
• 223268-52-8 2-<(1R)-3-methyl-1-(<(1'R)-1'-phenylethyl>amino)butyl>phenol 

Relevant academic research and scientific papers

Relay Catalysis by Achiral Borane and Chiral Phosphoric Acid in the Metal-Free Asymmetric Hydrogenation of Chromones

A strategy of relay catalysis by achiral borane and chiral phosphoric acid was successfully developed for the asymmetric hydrogenation of chromones, giving the desired products in high yields with up to 95% ee. Achiral borane and chiral phosphoric acid are highly compatible in this reaction. The achiral borane acts as a Lewis acid for the first-step hydrogenation, and the chiral phosphoric acid acts as an effective chiral proton shuttle to control the enantioselectivity.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

Structure-activity relationships of novel salicylaldehyde isonicotinoyl hydrazone (SIH) analogs: Iron chelation, anti-oxidant and cytotoxic properties

Salicylaldehyde isonicotinoyl hydrazone (SIH) is a lipophilic, tridentate iron chelator with marked anti-oxidant and modest cytotoxic activity against neoplastic cells. However, it has poor stability in an aqueous environment due to the rapid hydrolysis of its hydrazone bond. In this study, we synthesized a series of new SIH analogs (based on previously described aromatic ketones with improved hydrolytic stability). Their structure-activity relationships were assessed with respect to their stability in plasma, iron chelation efficacy, redox effects and cytotoxic activity against MCF-7 breast adenocarcinoma cells. Furthermore, studies assessed the cytotoxicity of these chelators and their ability to afford protection against hydrogen peroxide-induced oxidative injury in H9c2 cardiomyoblasts. The ligands with a reduced hydrazone bond, or the presence of bulky alkyl substituents near the hydrazone bond, showed severely limited biological activity. The introduction of a bromine substituent increased ligand-induced cytotoxicity to both cancer cells and H9c2 cardiomyoblasts. A similar effect was observed when the phenolic ring was exchanged with pyridine (i.e., changing the ligating site from O, N, O to N, N, O), which led to pro-oxidative effects. In contrast, compounds with long, flexible alkyl chains adjacent to the hydrazone bond exhibited specific cytotoxic effects against MCF-7 breast adenocarcinoma cells and low toxicity against H9c2 cardiomyoblasts. Hence, this study highlights important structure-activity relationships and provides insight into the further development of aroylhydrazone iron chelators with more potent and selective anti-neoplastic effects.

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

Targeting the gatekeeper residue in phosphoinositide 3-kinases

A single residue in the ATP binding pocket of protein kinases-termed the gatekeeper-has been shown to control sensitivity to a wide range of small molecule inhibitors (Chem. Biol. 2004, 11, 691; Chem. Biol. 1999, 6, 671). Kinases that possess a small side chain at this position (Thr, Ala, or Gly) are readily targeted by structurally diverse classes of inhibitors, whereas kinases that possess a larger residue at this position are broadly resistant. Recently, lipid kinases of the phosphoinositide 3-kinase (PI3-K) family have become the focus of intense research interest as potential drug targets (Chem. Biol. 2003, 10, 207; Curr. Opin. Pharmacol. 2003, 3, 426). In this study, we identify the residue that corresponds structurally to the gatekeeper in PI3-Ks, and explore its importance in controlling enzyme activity and small molecule sensitivity. Isoleucine 848 of p110α was mutated to alanine and glycine, but the mutated kinase was found to have severely impaired enzymatic activity. A structural bioinformatic comparison of this kinase with its yeast orthologs identified second site mutations that rescued the enzymatic activity of the I848A kinase. To probe the dimensions of the gatekeeper pocket, a focused panel of analogs of the PI3-K inhibitor LY294002 was synthesized and its activity against gatekeeper mutated and wild-type p110α was assessed.

Synthesis of 2,3-disubstituted benzofurans from ortho-acylphenols

2,3-Disubstituted benzofuran derivatives were synthesized from ortho-acylphenols in two steps. The β-aryloxyacrylates prepared from the ortho-acylphenols were treated with n-Bu3SnH/ AIBN and then with 5% HCl-EtOH to afford 2,3-disubstituted benzofurans. Georg Thieme Verlag Stuttgart.

Alkylation of dianions derived from 2-(1-iminoalkyl) phenols: Synthesis of functionalized 2-acyl phenols

A method has been developed for the almost exclusive C-alkylation of the 2-(l-liminoalkyl) phenols 1, important organic compounds with a range of employment, which allows the preparation of complex derivatives 4 with good yields starting from easily available materials. The operational simplicity of this method take advantages in providing a variety of alkylated 2-acyl phenols 5 by an easy hydrolysis of the 2-(1-iminoalkyl) phenols 4.

Chromenes and chromanones. Part IV.1 The Birch reduction of 2,2-dimethyl-4-chromanone and its 7-substituted analogues

2,2-Dimethyl-4-chromanone (1a), 2,2,7-trimethyl-4-chromanone (1b) and 7-methoxy-2,2-dimethyl-4-chromanone (1c) have been reduced by sodium or lithium in liquid ammonia with the presence or without of proton donor. The bicyclic or phenolic products were obtained. Products with reduced benzene ring only were also observed. The possible mechanisms of reductions are considered.