20845-80-1

Upstream product

• 186581-53-3 diazomethane 
• 645-45-4 hydrocinnamic acid chloride 
• 3277-89-2 phenethylmagnesium bromide 
• 79-04-9 chloroacetyl chloride 
• 622-24-2 2-phenylethyl chloride 
• 82772-38-1 α-(trichloromethyl)benzenepropanol 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 308796-14-7 phenethylzinc(II) bromide 
• 16520-62-0 4-Phenyl-1-butyne 
• 2344-70-9 1-phenyl-3-butanol 
• 2550-26-7 4-Phenyl-2-butanone 
• 67442-07-3 2-chloro-N-methoxy-N-methylacetamide 
• 90878-19-6 phenethylmagnesium chloride 
• 20296-07-5 1-hydroxy-4-phenyl-2-butanone 

Downstream Products

• 20296-08-6 1-acetoxy-4-phenyl-2-butanone 
• 159851-15-7 N-(2-oxo-4-phenyl-butyl)-phthalimide 
• 70080-77-2 2-amino-6-phenethyl-3,7-dihydro-pyrimido[4,5-b][1,4]oxazin-4-one 
• 134306-64-2 2-(3-phenylpropionylmethylseleno)benzothiazole 
• 352276-27-8 1-iodo-4-phenylbutan-2-one 
• 1821-12-1 4-Phenylbutyric acid 
• 2550-26-7 4-Phenyl-2-butanone 
• 22820-50-4 1-(isopropylamino)-4-phenylbutan-2-ol 
• 122218-14-8 4,4'-diphenethyl-2,2'-diphenyl-5,5'-selanediyl-bis-thiazole 
• 102831-08-3 1-azido-4-phenylbutan-2-one 
• 93434-80-1 1-phenyl-4-phenylsulphonylbutan-3-one 
• 1259944-09-6 3-hydroxy-2-phenylethylquinolin-4(1H)-one 
• 1373121-39-1 C₂₆H₂₄N₂O₃ 
• 1373121-58-4 C₁₈H₁₉ClN₂O₂ 

Relevant academic research and scientific papers

Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent "ene"-Reductases

α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent ‘ene'-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.

Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.

Palladium-Catalyzed C–C Ring Closure in α-Chloromethylimines: Synthesis of 1H-Indoles

The C-C ring closure of α-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or commercially available α-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.

A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant

α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).

Direct conversion of alcohols to α-chloro aldehydes and α-chloro ketones

Direct conversion of primary and secondary alcohols into the corresponding α-chloro aldehydes and α-chloro ketones using trichloroisocyanuric acid, serving both as stoichiometric oxidant and α-halogenating reagent, is reported. For primary alcohols, TEMPO has to be added as an oxidation catalyst, and for the transformation of secondary alcohols (TEMPO-free protocol), MeOH as an additive is essential to promote chlorination of the intermediary ketones.

Electrophilicity of α-oxo gold carbene intermediates: Halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones

α-Oxo gold carbenes generated via intermolecular oxidation of terminal alkynes are shown to be highly electrophilic and can effectively abstract halogen from halogenated solvents such as 1,2-dichloroethane or 1,2-dibromoethane. Chloro/bromomethyl ketones are prepared in moderate efficiencies in one step using Ph3PAuNTf2 as the catalyst and 8-methylquinoline N-oxide as the oxidant.

Studies on the chemistry and reactivity of α-substituted ketones in isonitrile-based multicomponent reactions

(Chemical Equation Presented) Using the Passerini and Ugi reactions as representative tests, the utility of several α-substituted ketones R-CO-CH2-X (X = sulfonyloxy, acyloxy, azido, halo, hydroxy, and sulfonyl) in isonitrile-based multicompone

Copper(I)-promoted synthesis of chloromethyl ketones from trichloromethyl carbinols

(Chemical Equation Presented) Reaction of several trichloromethyl carbinols with 2 equiv of CuCl/bpy in refluxing DCE for 3 h afforded chloromethyl ketones in excellent yield by 1,2-H shift in the copper-chlorocarbenoid intermediate.

Methods and Compositions for Treatment of Scleritis and Related Disorders

The present teachings relate to the field of anti-inflammatory substances and more particularly to compounds that are useful for the treatment of scleritis, a scleritis symptom, or a scleritis-related disorder. In one aspect, methods of treating scleritis, a scleritis symptom, or a scleritis-related disorder generally include administering to a subject a compound of Formula I: or a pharmaceutically acceptable salt, hydrate or ester thereof, wherein W1, W2, R1, L, X, Y, Z, and n1 are defined as described herein.

A mechanistic study of the chromium(II)-mediated transformations of trichloromethyl alkyls and carbinols: evidence for carbene, carbyne, and carbenoid intermediates

Using CrCl2 in THF at room temperature, trichloromethyl carbinols and trichloromethylalkanes are readily transformed to the highly reactive α-chlorocarbenes, carbynes and α-chloro-α-chromium(III) vinylidene carbenoids. A mechanistic study is carried out to determine the nature of the intermediates.