885-75-6

Usage

Main properties

1. Chemical compound
2. Molecular formula: C14H13NO
3. Aromatic and carbonyl functional groups
4. Used in organic synthesis and pharmaceutical research

Specific content

1. Reagent in organic synthesis and pharmaceutical research
2. Known for aromatic and carbonyl functional groups
3. Studied for potential biological and pharmacological properties
4. Investigated for potential application in drug development
5. Demonstrated potential as an intermediate in the synthesis of various organic compounds

Upstream product

• 109-06-8 α-picoline 
• 14257-84-2 N-acetyl-α-phenylglycine 
• 93-97-0 benzoic acid anhydride 
• 3893-31-0 N-(2-oxo-1,2-diphenylethyl)acetamide 
• 32493-66-6 2-(2-oxo-1,2-diphenylethyl)isoindoline-1,3-dione 
• 169899-58-5 2-(1-hydroxy-1-phenylmethyl)-4,5-dimethylthiazole 
• 100-58-3 phenylmagnesium bromide 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 451-40-1 phenyl benzyl ketone 
• 100-52-7 benzaldehyde 
• 98837-46-8 N-benzylidenediphenylphosphinamide 
• 5908-41-8 benzoyltrimethylsilane 
• 801219-76-1 2-(diphenylphosphinamide)-1,2-diphenylethanone 
• 1484-50-0 desyl bromide 

Downstream Products

• 854228-62-9 2-amino-1,2-diphenyl-1-o-tolyl-ethanol 
• 3893-31-0 N-(2-oxo-1,2-diphenylethyl)acetamide 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 102474-68-0 (1RS,2RS)-2-amino-1,2-diphenyl-1-p-tolyl-ethanol 
• 58417-78-0 α-Benzoylbenzyldithiocarbaminsaeure-methylester 
• 200802-49-9 4-Cyanomethyl-N-(2-oxo-1,2-diphenyl-ethyl)-benzamide 
• 6942-03-6 α-benzamidylbenzyl phenyl ketone 
• 15045-46-2 4-nitro-N-(2-oxo-1,2-diphenylethyl)benzamide 
• 102474-68-0 (1Ξ,2S)-2-amino-1,2-diphenyl-1-p-tolyl-ethanol 
• 1826-15-9 4,5-diphenylthiazole 
• 65996-43-2 N₁-(1-methyl-2-oxo-2-phenylethyl)-4-methyl-1-benzenesulfonamide 

Relevant academic research and scientific papers

Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones

A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent, and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective synthesis of an MDM2-p53 inhibitor precursor.

Synthesis of functionalized imidazolidine-2-thiones: Via NHC/base-promoted aza-benzoin/aza-acetalization domino reactions

A strategy for the synthesis of biologically relevant 5-hydroxy-imidazolidine-2-thione derivatives is presented. A novel class of α-sulfonylamines have been suitably prepared (46-81% yield) as precursors of formal benzylidenethiourea acceptors; these are generated in situ and intercepted by N-heterocyclic carbene (NHC)-activated aldehydes affording open-chain aza-benzoin-type adducts, which in turn undergo an intramolecular aza-acetalization reaction in a one-pot fashion. A thiazolium salt/triethylamine couple proved to be the more effective system to trigger the domino sequence giving the target heterocycles in good yields (45-97%) and diastereoselectivities (up to 99 : 1 dr). The multigram scale synthesis and elaboration of a selected 5-hydroxy-imidazolidine-2-thione compound is also described.

Concise synthesis of 1H-pyrazin-2-ones and 2-aminopyrazines

Convenient syntheses of 1H-pyrazin-2-ones and 2-aminopyrazines are described. By coupling Boc-protected amino acids with α-amino ketones or with amino alcohols and subsequent oxidation, 1H-pyrazin-2-ones were obtained. Transformation into the corresponding pyrazine triflates and substitution with primary or secondary amines led to 2-aminopyrazines. Since these syntheses take advantage of the use of readily available starting materials (e.g., amino acids, aminoalcohols and amines) a variety of the entitled structures can be obtained in few, high yielding steps.

Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones

(Chemical Equation Presented) The addition of acylsilanes to imines catalyzed by neutral carbenes (or zwitterions) generated in situ from readily available thiazolium salts is described. The general reaction successfully utilizes acylsilanes as carbonyl anion precursors and is tolerant of a range of structural diversity on the acylsilane or imine electrophile. The overall reaction utilizes easily available precursors and directly accesses protected α-amino ketones in the correct oxidation state.

Pyrrolomorphinans as δ opioid receptor antagonists. The role of steric hindrance in conferring selectivity

A series of 2',3'-disubstituted pyrrolomorphinans (5a-i) were synthesized to determine the role of steric hindrance at μ and γ receptors in promoting δ opioid receptor antagonist selectivity. In smooth muscle preparations, five members of the series (5a-c,e,f) possessed K(e) values in the range 2-15 nM and were 6 selective. Since the unsubstituted analogue 4 possessed δ antagonist potency of similar magnitude, but was not δ selective, it is suggested that the 2',3'substitution confers δ selectivity by hindering the interaction of the pharmacophore at μ and γ receptors, while not affecting δ receptors.