20907-24-8

Upstream product

• 71292-79-0 diethyl 1-trimethylsilyloxy-3-methyl-2-oxo-1-phenylbutylphosphonate 
• 100-39-0 benzyl bromide 
• 109334-46-5 N-methyl-2-S-benzylthioaniline 
• 582-62-7 3-methyl-1-phenylbutan-1-one 
• 100-52-7 benzaldehyde 
• 78-84-2 isobutyraldehyde 
• 82187-05-1 N-(2-Benzylsulfanyl-phenyl)-N-methyl-isobutyramide 
• 82187-14-2 3-Methyl-1-(2-methylamino-phenylsulfanyl)-1-phenyl-butan-2-one 
• 31675-43-1 diethyl 1-phenyl-1-(trimethylsiloxy)methanephosphonate 
• 80325-69-5 1-Chlor-2-isopropyl-1-phenyloxiran 

Downstream Products

• 104426-40-6 3-methyl-1-oxo-1-phenylbutan-2-yl acetate 
• 7332-95-8 3-methyl-1-phenylbutane-1,2-dione 

Relevant academic research and scientific papers

Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement

α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.

SMALL MOLECULE NEUTRAL SPHINGOMYELINASE 2 (NSMASE2) INHIBITORS

Small molecule inhibitors of neutral sphingomyelinase 2 (nSMase2) and their use for treating neurodegenerative diseases, such as, neurodegenerative diseases associated with high levels of ceramide, including, but not limited to Alzheimer's disease (AD), H

Neutral sphingomyelinase 2 inhibitors based on the 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol scaffold

Neutral sphingomyelinase 2 (nSMase2), a key enzyme in ceramide biosynthesis, is a new therapeutic target for the treatment of neurological disorders and cancer. Using 2,6-dimethoxy-4-[4-phenyl-5-(2-thienyl)-1H-imidazol-2-yl]phenol (DPTIP), our initial hit compound (IC50 = 30 nM) from nSMase2 screening efforts, as a molecular template, a series of 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol derivatives were designed, synthesized, and evaluated. Systematic examination of various regions of DPTIP identified the key pharmacophore required for potent nSMase2 inhibition as well as a number of compounds with the 4-(1H-imidazol-2-yl)-2,6-dialkoxyphenol scaffold with similar or higher inhibitory potency against nSMase2 as compared to DPTIP. Among them, 4-(4,5-diisopropyl-1H-imidazol-2-yl)-2,6-dimethoxyphenol (25b) was found to be metabolically stable against P450 metabolism in liver microsomes and displayed higher plasma exposure following oral administration as compared to DPTIP. Analysis of plasma samples identified an O-glucuronide as the major metabolite. Blockade of the phase II metabolism should further facilitate our efforts to identify potent nSMase2 inhibitors with desirable ADME properties.

Chemoselective and repetitive intermolecular cross-acyloin condensation reactions between a variety of aromatic and aliphatic aldehydes using a robust N-heterocyclic carbene catalyst

We found that chemoselectivity of the crossed acyloin product is controlled by the adjustment of the aromatic aldehyde/aliphatic aldehyde ratio. Moreover, we observed the persistent catalytic activity of the homogeneous NHC catalyst in a solution due to N

Benzaldehyde lyase-catalyzed diastereoselective C-C bond formation by simultaneous carboligation and kinetic resolution

Enzymes create chiral microenvironments that may simultaneously generate several stereogenic centers in the same catalytic cycle, broadening the possibilities of biocatalysis. Benzaldehyde lyase (BAL) affords highly diastereoselective α-hydroxy-ketones by simultaneously performing ligation and kinetic resolution of a racemic aldehyde. Thus, to the well-known enantioselective BAL-carboligation of aldehydes (C-C bond formation), another property, namely diastereoselectivity, is added in this paper for the first time.

Highly chemoselective direct crossed aliphatic-aromatic acyloin condensations with triazolium-derived carbene catalysts

It has been shown for the first time that triazolium precatalysts promote (in the presence of base) highly chemoselective crossed acyloin condensation reactions between aliphatic and ortho-substituted aromatic aldehydes. An o-bromine atom can serve as a temporary directing group to ensure high chemoselectivity (regardless of the nature of the other substituents on the aromatic ring) which then can be conveniently removed. The process is of broad scope and is operationally simple as it does not require the preactivation of any of the coupling partners to ensure selectivtiy. Preliminary data indicate that highly enantioselective variants of the reaction are feasible using chiral precatalysts.

Medium-ring Ketone Synthesis. Intramolecular Acylation of Sulfur-stabilized Carbanions: A Model Study

Intramolecular acylation of the sulfur-stabilized carbanions of the acyclic ester 9 and amide sulfides 11 was carried out as a model study for developing an effective method for the construction of medium-ring ketones by ring closure.Reaction of 9a-c or 11a-g with lithium diisopropylamide (LDA) proceeded smoothly and the expected keto sulfides 10a-c or 12a-g, respectively, were obtained.In the cases where R1 and/or R2 in 11 were normal alkyl groups, the reaction did not take place.However, these difficulties were readily overcome either by introducing a methyl group next to the carbonyl group or by converting the sulfides into the corresponding sulfoxides or sulfones.Acylation in the allyl sulfides 11b, d, f and the allyl sulfone 20b takes place at the α-position to the sulfur atom, yielding β,γ-unsaturated ketones.A reductive removal of the sulfide moiety or its conversion into other functional groups was also examined.

A New Type of P-C and C-C Bond Cleavage Reactions in α-Trimethylsilyloxy-β-oxo Phosphonates and α-Ethoxy-β-oxo Phosphonates. The Synthesis of Unsymmetrical α-Hydroxy Ketones Utilizing 1:1 Carbonyl Adducts of Diethyl Trimethylsilyl Phosphite with Benzaldehyde

α-Lithiated diethyl α-(trimethylsilyloxy)benzylphosphonate underwent facile acylation with various acylating agents to afford the corresponding α-acylated products in good yields.On treatment with the α-acylated products with 1 M NaOH-EtOH (1:1, v/v) the P-C bond was cleaved with elimination of diethyl phosphate to give α-hydroxy ketones predominantly.On the other hand, when diethyl α-acyl-α-ethoxybenzylphosphonates were treated under the same conditions, they were rather stable and recovered.However, the prolonged alkaline treatment or the use of 4 M NaOH-EtOH (1:1 v/v) resulted in the C-C bond cleavage giving carboxylic acids and diethyl α-ethoxybenzylphosphonate in quantitative yields, respectively.The mechanisms of the above two reactions were proposed and discussed in connection with the Perkow reaction and related reactions.