41693-11-2

Upstream product

• 539-82-2 ethyl n-valerate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 26818-07-5 1-bromo-2-hexanone 
• 603-35-0 triphenylphosphine 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 638-29-9 n-valeryl chloride 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 693-03-8 n-butyl magnesium bromide 
• 73818-55-0 Bestmann ylide 

Relevant academic research and scientific papers

Carboprost tromethamine related impurity L-amyl 15-ketone and preparation method thereof

The invention relates to a carboprost tromethamine related impurity L-amyl 15-ketone and a preparation method thereof. The preparation method comprises the following steps of: (1) in the presence of afifth organic solvent, carrying out dehydrogenation reaction on methyl triphenyl phosphine halide by using strong base, adding ethyl valerate after reaction for a certain time, continuously reactingfor a certain time to obtain 1-triphenylphosphine 2-hexanone; and (2) carrying out wittig reaction on the 1-triphenylphosphine 2-hexanone obtained in the step (1) and a second organic solvent solutionof benzoyl corey lactone aldehyde to obtain a pentyl-15 ketone crude product. The method has the advantages of simple and convenient operation, high safety, and high yield and purity of an obtained product under optimal conditions, and can meet the requirements for impurity research.

Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction

NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

Synthesis and Biological Evaluation of Tricyclic Guanidine Analogues of Batzelladine K for Antimalarial, Antileishmanial, Antibacterial, Antifungal, and Anti-HIV Activities

Fifty analogues of batzelladine K were synthesized and evaluated for in vitro antimalarial (Plasmodium falciparum), antileishmanial (Leishmania donovani), antimicrobial (panel of bacteria and fungi), antiviral (HIV-1) activities. Analogues 14h and 20l exhibited potential antimalarial activity against chloroquine-sensitive D6 strain with IC50 1.25 and 0.88μm and chloroquine-resistant W2 strain with IC50 1.64 and 1.07μm, respectively. Analogues 12c and 14c having nonyl substitution showed the most potent antileishmanial activity with IC50 2.39 and 2.78μm and IC90 11.27 and 12.76μm, respectively. Three analogues 12c, 14c, and 14i were the most active against various pathogenic bacteria and fungi with IC503.02μm and MIC/MBC/MFC 6μm. Analogue 20l having pentyl and methyl substituents on tricycle showed promising activities against all pathogens. However, none was found active against HIV-1. Our study demonstrated that the tricyclic guanidine compounds provide new structural class for broad spectrum activity. Fifty analogues of tricyclic guanidine derivative of batzelladine K were synthesized and tested for antimalarial, antileishmanial, antimicrobial, antifungal and anti-HIV activities. We have identified several active analogues.

High-pressure accelerated asymmetric organocatalytic friedel-crafts alkylation of indoles with enones: Application to quaternary stereogenic centers construction

An organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones was found to be efficiently accelerated under high-pressure conditions with a low loading of chiral primary amine salts with good yield and enantioselectivity up to 90%. This approach also allows, for the first time, selected indole derivatives containing quaternary stereogenic centers to be obtained from prochiral β,β-disubstituted enones with an enantioselectivity up to 80%.

Conversion of conjugated enones into enantiomerically pure β-hydroxy ketones or 1,3-diols - Samarium(II) bromide reductions of protected α,β-dihydroxy ketones

Asymmetric dihydroxylations of α,β-unsaturated ketones in the presence of Sharpless' AD mix-β delivered α,β-dihydroxy ketones or, if phenylboronic acid was present, the corresponding phenylboronates. The Cα-O bonds of these species were removed

Cumulated Ylides XIX. Chain-lenghthening Difunctionalization of Grignard Compounds by Reaction with Ketenylidenetriphenylphosphorane. A New Route to (E)-α,β-Unsaturated Ketones and the Queen Substance

The reaction of Grignard compounds with ketenylidenetriphenylphosphorane and subsequent hydrolysis yields 2-oxoalkylidenetriphenylphosphoranes.The latter undergo Wittig reaction, whereby (E)-α,β-unsaturated ketones are obtained.An application of this strategy to the synthesis of carbonyl homologues of Lepidoptera pheromones and the queen substance is shown.