50874-13-0

Upstream product

• 67-56-1 methanol 
• 16169-88-3 1-phenylprop-2-ynyl acetate 
• 134225-41-5 N-((phenylethynyl)methylene)-trans-2,3-diphenyl-1-aziridinamine 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 74-88-4 methyl iodide 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 104846-76-6 (±)-methyl (1-phenylprop-2-yn-1-yl) carbonate 
• 100-52-7 benzaldehyde 
• 77-78-1 dimethyl sulfate 
• 118804-16-3 1-methoxy-4,4-dimethyl-1-phenyl-4-sila-2-pentyne 
• 1794-48-5 1-bromo-3-phenylprop-2-yne 
• 50874-12-9 (3-Phenyl-prop-2-ynyl)-carbamic acid methyl ester 
• 2579-22-8 Phenylpropargyl aldehyde 
• 51094-85-0 C₁₁H₁₀N₂O₃ 

Downstream Products

• 7624-24-0 1-methoxy-1-phenyl-acetone 
• 83564-77-6 4-methoxy-4-phenylbut-2-yn-1-ol 
• 118804-16-3 1-methoxy-4,4-dimethyl-1-phenyl-4-sila-2-pentyne 
• 40025-32-9 2-n-propyl-5-phenylfuran 
• 955-83-9 2,5-diphenylfuran 
• 4482-17-1 1,4-diphenyl-but-2-yne-1,4-diol 
• 495-71-6 phenacylacetophenone 
• 31650-07-4 1-phenyl-3-(trimethylsilyl)-1,2-propadiene 
• 1189021-19-9 methyl 4-methoxy-4-phenyl-2-butynoate 
• 1338795-56-4 (E)-2-(3-methoxy-3-phenylprop-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1361962-68-6 1-(1-ethyl-1H-indol-2-yl)-4-phenylbuta-2,3-dien-1-ol 
• 1361962-69-7 C₂₁H₂₁NO₂ 
• 14371-10-9 (E)-3-phenylpropenal 
• 1207847-62-8 4-(methoxy(phenyl)methyl)-2-phenylquinoline 

Relevant academic research and scientific papers

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

HBF4-Catalysed Nucleophilic Substitutions of Propargylic Alcohols

The activity of HBF4 (aqueous solution) as a catalyst in propargylation reactions is presented. Diverse types of nucleophiles were employed in order to form new C-O, C-N and C-C bonds in technical acetone and in air. Good to excellent yields and good chemoselectivities were obtained using low acid loading (typically 1 mol-%) under simple reaction conditions. The activity of HBF4 (aq. solution) as a catalyst in propargylation reactions is presented. C-O, C-N and C-C bonds were formed in technical acetone and in air. Good to excellent yields were obtained using low acid loading (typically 1 mol-%) under mild reaction conditions.

Gold(I)-catalyzed decarboxylation of propargyl carbonates: Reactivity reversal of the gold catalyst from π-Lewis acidity to σ-Lewis acidity

A cationic gold(I)-catalyzed decarboxylative etherification of propargyl carbonates to selectively produce propargyl ethers is reported. In the reaction the gold(I) catalyst shows a distinct σ-Lewis acidity rather than the commonly observed π-Lewis acidity, and thus catalyzes the decarboxylation of a variety of propargyl carbonates to give the corresponding propargyl ethers with high selectivity. This reaction represents a rare example of the tunable reactivity of cationic gold(I) complexes between σ-Lewis acidity and π-Lewis acidity.

Cobaltocene-induced low-temperature radical coupling reactions in a cobalt-alkyne series

A novel method for the low-temperature generation of Co2(CO) 6-complexed propargyl radicals is developed. It consists of an in situ preparation of the respective cationic species (-50 to -10 °C) and their rapid reduction with cobaltocene, Cp2Co, at -50 °C. The optimized experimental protocol is applied to both inter- and intramolecular reactions, affording topologically diverse α-aryl and α-napthyl, d,l- and meso-1,5-hexadiynes and 1,5-cyclodecadiynes. The d,l configuration is the most preferable steric arrangement in intermolecular radical C-C bond-forming reactions (d,l 69-92%), while a reversal of stereoselectivity is observed in intramolecular cyclizations (meso 79%). Under oxidizing conditions (Ce4+), decomplexation affords d,l-3,4-diaryl- and d,l-3,4-(1-/2-naphthyl)-1,5-hexadiynes in good to excellent yields (47-98%). An enhanced functional tolerance is showcased by introducing peripheral acid-sensitive functionalities, such as benzyloxy and methylenedioxy groups, and carrying out a five-step conversion scheme-from commercial aromatic aldehydes to radical dimers-under nonacidic conditions.

KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME

The present teachings provide a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. Also described are a pharmaceutical composition and method of use thereof.

Resolution of carboxylic acids using copper(I)-promoted removal of propargylic esters under neutral conditions

A method for the optical resolution of carboxylic acids is described. Condensation of racemic carboxylic acids with chiral terminal propargyl alcohols gave separable diastereomeric esters. Chromatographic separation followed by heating the individual diastereomers in methanol with catalytic copper(I) halide regenerated the carboxylic acids in good yields and in enantiomeric ratios of ?94%. This method is particularly useful for the resolution of carboxylic acids that are incompatible with conventional ester hydrolysis.

Gold-catalyzed synthesis of bicyclo[3.2.0]heptenes via a formal [3+2]/[2+2]-annulation of allylsilane with 4-methoxybut-2-yn1-ols

This work reports the novel gold-catalyzed [3+ 2]/[2+2]-annulation of allylsilane with Amethoxybut-2-yn-l-ols that yields highly strained bicyclo[3.2.0]heptene products efficiently and stereoselectively.

Cationic rhodium(I)/bisphosphane complex-catalyzed isomerization of secondary propargylic alcohols to α,β-enones

We have determined that hydrogenated cationic Rh(I)/bisphosphane complexes are highly active catalysts for the isomerization of secondary propargylic alcohols to α,β-enones. A kinetic resolution of secondary propargylic alcohols proceeded with moderate selectivity with [Rh((R)-BINA-P)]OTf as a catalyst. Mechanistic studies revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways. The isomerization of propargylic diol derivatives was also investigated, which revealed that 1,4-diketones, furans, and α,β-enones were obtained from 2-butyn-1,4-diol, 1-methoxy-2-butyn-4-ol, and 1-acetoxy-2-butyn-4-ol derivatives, respectively. Furthermore, chemoselectivity of the isomerization of an acetylenic diol was investigated, and preferential oxidation of a propargylic hydroxy group was observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Palladium-catalyzed silastannation of secondary propargylic alcohols and their derivatives

A series of terminal propargylic alcohols and their derivatives were subjected to Pd-catalyzed silastannation. In all reactions, complete regio- and stereoselectivities were observed with the tributyltin moiety exclusively adding to the internal carbon of the triple bond in a cis fashion, including the first example of a diyne bis-silastannation. Silastannation reaction products could sequentially be protiodesilylated or iododestannylated, thus providing synthetic routes to 1,1-gem-disubstituted alkenylstannanes and iodides, respectively.

TiCl4-mediated nucleophilic substitution of propargylic esters

Direct displacement reactions of propargylic esters are reported. 10 mol% of TiCl4 were used to carry out a nucleophilic substitution. Scope and limitation of this novel reaction are described. (C) 2000 Elsevier Science Ltd.