1771-65-9

Usage

Uses

2-Methyl-4-oxo-4-phenylbutyric Acid is a chemical reagent used in the synthesis of various pharmaceutically active compounds. Used in the synthesis of Minozac, a suppressor of brain proinflammatory cytokine up-regulation.

General Description

2-Methyl-4-oxo-4-phenylbutyric acid is a butyric acid derivative.

InChI:InChI=1/C11H12O3/c1-8(11(13)14)7-10(12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,13,14)

Upstream product

• 495-41-0 1-phenylbut-2-en-1-one 
• 15732-75-9 3-benzoyl-2-methylenepropionic acid 
• 15121-71-8 (E)-2-methyl-3-benzoylpropenoic acid 
• 336624-91-0 2-methyl-4-oxo-4-phenyl-cis-crotonic acid 
• 70-11-1 α-bromoacetophenone 
• 609-08-5 Diethyl methylmalonate 
• 4100-80-5 2-methylsuccinic anhydride 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 16002-63-4 phenylmagnesium iodide 
• 14308-32-8 2,2-diethoxy-3-methyl-5-phenyl-2,3-dihydro-furan 
• 88670-17-1 5-isopropyl-2-methyl-7a-phenylhexyhydropyrrolizin-3-one 
• 113549-23-8 5-methyl-3-phenyl-6H-1,2-oxazin-6-one 
• 71819-05-1 4-methyl-2-morpholin-4-yl-2-phenyl-pentanedinitrile 

Downstream Products

• 109251-79-8 4-methyl-2-(1-methyl-[4]piperidyl)-6-phenyl-2H-pyridazin-3-one 
• 52239-91-5 4-methyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one 
• 1949-41-3 2-methyl-4-phenylbutanoic acid 
• 53515-28-9 3-bromo-2-methyl-4-oxo-4-phenyl-butyric acid 
• 603-54-3 N,N-diphenylurea 
• 36057-38-2 2-methyl-4-oxo-4-phenyl-butyric acid methyl ester 
• 1590-08-5 2-methyl-1-tetralone 
• 75380-99-3 succinimido 3-benzoyl-2-methylpropionate 
• 15121-74-1 3-methyl-5-phenylfuran-2(3H)-one 
• 84143-18-0 (S)-2-Methyl-4-oxo-4-phenylbutanoic acid 
• 84143-17-9 (R)-2-methyl-4-oxo-4-phenylbutanoic acid 
• 41927-29-1 (S)-2-methyl-4-phenyl-1-butyric acid 
• 80651-37-2 (R)-(-)-2-methyl-4-phenylbutyric acid 
• 33268-39-2 2-methyl-4-oxo-4-phenyl-butyric acid anilide 

Relevant academic research and scientific papers

gamma-alkenyl ketone and preparation method thereof

The invention discloses a gamma-alkenyl ketone preparation method, wherein the target product can be obtained at high yield and high regioselectivity by using acetophenone and 1,3-butadiene as raw materials in the presence of an organic solvent, a catalyst, an additive and a ligand. According to the invention, the method has advantages of high atom economy, high regioselectivity, high yield and the like, can achieve the efficient conversion from a cheap basic organic chemical product 1,3-butadiene to high-added-value gamma-alkenyl ketone, and uses the cheap catalyst, so that the reaction conditions are neutral and mild, and the experimental operation is safe and simple; and the synthesized gamma-alkenyl ketone is a useful synthetic intermediate, can be subjected to a series of conversionsto obtain a series of drug molecule precursors or key intermediates, and has wide application prospect.

Pd(ii)/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids

An efficient Pd/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids is described. This methodology offers a divergent synthesis of α-methyl-γ-keto carboxylic acids, α-methylcarboxylic acids, and lactones starting from α-me

Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation

A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).

A simple synthesis of α-methyl-γ-keto acids

The reaction of the anion derived from α-marpholinonitriles with methyl acrylate in excess of NaH in DMF gives γ-keto acids in high yield. This process is highly convenient for the synthesis of various α-substituted-γ-keto acids, which can be easily converted to naturally occurring α-substituted -γ-lactones.

CASPASE INHIBITOR COMPRISING 2-ALKYL-4-OXOBUTANOYL GROUP AND PHARMACEUTICAL COMPOSITION THEREOF

The present invention relates to a compound of the formula (1), pharmaceutically acceptable salt, physiologically hydrolysable ester, hydrate, solvate, or steroisomer thereof having inhibitory activity against caspases. The compound contains unknown new 2

THERAPEUTIC AGENT FOR DIABETES

A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

Nonsteroidal Progesterone Receptor Ligands. 2. High-Affinity Ligands with Selectivity for Bone Cell Progesterone Receptors

A novel series of nonsteroidal heterocycles was discovered which display cell-type selective, high-affinity (nanomolar) binding to the progesterone receptors from TE85 osteosarcoma cells but > 1 μM binding affinity to the progesterone receptors from T47D and ZR75 human breast carcinpma cells.Structure-activity relationships were developed for a set of these compounds, and a representative analog 1-(3,4-dichlorobenzoyl)-3-phenyl-1,4,5,6-tetrahydropyridazine (1i, RWJ 25333) was chosen for further evaluation.RWJ 25333 stimulated the in vitro proliferation of human osteoblast-like cells but not human breast cells.

Model Studies of the Reduction of 3-Phenyl-6H-1,2-oxazines, Chemo- and Stereoselectivity: Synthesis of Amino Alcohols, Amino Acids, and Related Compounds

While palladium-catalyzed hydrogenation of 3-phenyl-6H-1,2-oxazine 1 produces primary amine 5 in a nitrogen-transposition reaction, the reductions of the related 1,2-oxazines 2, 10, and the 1,2-oxazin-6-one 3 afford the expected amino alcohols 4, 11, and the γ-amino acid 6, respectively, with low diastereoselectivities.In the presence of acetic acid 3 is reductively converted into γ-keto carboxylic acid 9 and 1 into the γ-lactam derivative 12 probably by a ring contraction to a nitrone intermediate.Raney nickel as the catalyst is able to transform 1,2-oxazine 7 bearing an exo-methylene unit into 3,4-dihydro-2H-pyrrole 13.The reaction of 6H-1,2-oxazine 1 with aluminium amalgam produces pyrrole 14 in moderate yield.Treatment of 1 with sodium in 2-propanol brings about its transformation into pyrrolidine derivative 15 together with pyrrole 14 and amino alcohol 4 as minor products.The chemoselectivity and stereoselectivity of these reductions are discussed including mechanistic proposals for the multistep processes involved. Key Words: 1,2-Oxazines / Hydrogenation, catalytic / Amino alcohols / γ-Amino acids / Pyrroles / γ-Lactams

Allylic Rearrangement of Cyanophosphates. III. Reaction of Acyclic Enone Cyanophosphates

Boron trifluoride-catalyzed allylic rearrangement of α,β-unsaturated ketone cyanophosphates (2, 6 and 12) gave (Z)-4-diethylphosphonooxy-2-butenenitriles (3, 8 and 13), while α,β-unsaturated aldehyde cyanophosphates (17a-c) afforded (E)-4-diethylphosphonooxy-2-butenenitriles (18a-c) stereoselectively.The stereo- and regioselective reaction of 2 with several kinds of aromatics in the presence of boron trifluoride etherate afforded (Z)-4-aryl-2-methyl-2-butenenitriles (20) via the SN2' reaction.On the other hand, treatment of 2 with 1-substituted indoles in the presence of boron trifluoride etherate gave 1-amino-2-methylcarbazole derivatives (23a-c).Keywords-α,β-unsaturated ketone; α,β-unsaturated aldehyde; cyanophosphate; allylic rearrangement; boron trifluoride etherate; 2-butenenitrile derivative; SN2' reaction; 1-aminocarbazole derivative

ON THE QUANTITATIVE RELATIONS BETWEEN STRUCTURE AND ANTIAGGREGATION ACTIVITY OF ω-ARYL-ω-OXOALKANOIC ACIDS

A series of ω-aryl-ω-oxoalkanoic acids, I-IV, has been prepared and investigated for dissociation constants in 80percent methylcellosolve, retention characteristics in thin-layer partition chromatography and partition coefficients P in the system octanol-water.Also evaluated were their anti-inflammatory efficacy and inhibitory effect on the platelet aggregation induced by collagen.Analysing the relations between structure and antiaggregation effect, we obtained a non-linear, quadratic dependence of this effect on lipophilicity, the optimum being at log P = 3.The antiaggregation effect increased with shortening the chain between the carbonyl and the carboxyl, and with increasing acidity.It was also diminished by the presence of a methyl group on the interlinking chain.To assess the role of lipophilicity we used the RM values of partition chromatography.The relation between anti-inflammatory efficacy and structure was assessed only qualitatively.In this aspect, too, the nature of the chain between the carbonyl and carboxyl proved to have a marked influence.The anti-inflammatory activity proved considerably enhanced by the presence of another aromatic ring in ω-oxoalkanoic acids derived from biphenyl.