2214-14-4

Upstream product

• 17343-73-6 (2,2-dibromo-1-methylcyclopropyl)benzene 
• 3591-42-2 1,1-dichloro-2-methyl-2-phenylcyclopropane 
• 515-40-2 neophyl chloride 
• 676-54-0 ethyl sodium 
• 109-66-0 pentane 
• 98-83-9 isopropenylbenzene 
• 75-11-6 diiodomethane 
• 2085-88-3 2-methyl-2-phenyloxirane 
• 76373-10-9 (trimethylstannyl)methyl-lithium 
• 82518-02-3 3-(2-phenyl-2-propyl)diazirine 
• 3100-04-7 Methylcyclopropen 
• 873-49-4 cyclopropylbenzene 
• 74-88-4 methyl iodide 
• 67-66-3 chloroform 

Downstream Products

• 40088-87-7 1-methyl-1-(o-nitrophenyl)cyclopropane 
• 40088-88-8 1-methyl-1-(4-nitrophenyl)cyclopropane 
• 42427-46-3 p-(1-Methylcyclopropyl)acetophenone 
• 87243-56-9 5-Methyl-5-phenyl-4,5-dihydroisoxazole 
• 98-86-2 acetophenone 
• 137601-89-9 p-(1-Methylcyclopropyl)-α-methylbenzyl Alcohol 
• 137601-79-7 p-(1-Methylcyclopropyl)-α-methylbenzyl Chloride 
• 1188906-50-4 3-phenyl-3-chlorobutyronitrile 
• 14368-40-2 (E)-3-phenyl-2-butenenitrile 
• 71759-33-6 1-methyl-1-(o-aminophenyl)cyclopropane 
• 1403387-80-3 4-bromo-2-(1-methylcyclopropyl)aniline 
• 1403387-81-4 4-bromo-2-(1-methylcyclopropyl)benzene-1-sulfonyl chloride 
• 1403387-82-5 4-bromo-N-(tert-butyl)-2-(1-methylcyclopropyl)benzenesulfonamide 
• 1403387-79-0 N-(tert-butyl)-2-(1-methylcyclopropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Silylium-Ion-Promoted Ring-Opening Hydrosilylation and Disilylation of Unactivated Cyclopropanes

A silylium-ion-promoted ring-opening hydrosilylation of unactivated cyclopropanes is reported. The reaction is facilitated by the γ-silicon effect, and the regioselectivity is influenced by various stabilizing effects on the carbenium-ion intermediates, including the β-silicon effect. The experimental observations are in accord with the computed reaction mechanism. The work also showcases the ability of silylium ions to isomerize cyclopropyl to allyl groups, and the resulting α-olefins engage in a silylium-ion-mediated disilylation with hexamethyldisilane.

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Direct Synthesis of Cyclopropanes from gem-Dialkyl Groups through Double C-H Activation

Cyclopropanes are important structural motifs found in numerous bioactive molecules, and a number of methods are available for their synthesis. However, one of the simplest cyclopropanation reactions involving the intramolecular coupling of two C-H bonds on gem-dialkyl groups has remained an elusive transformation. We demonstrate herein that this reaction is accessible using aryl bromide or triflate precursors and the 1,4-Pd shift mechanism. The use of pivalate as the base was found to be crucial to divert the mechanistic pathway toward the cyclopropane instead of the previously obtained benzocyclobutene product. Stoichiometric mechanistic studies allowed the identification of aryl- and alkylpalladium pivalates, which are in equilibrium via a five-membered palladacycle. With pivalate, a second C(sp3)-H activation leading to the four-membered palladacycle intermediate and the cyclopropane product is favored. A catalytic reaction was developed and showed a broad scope for the generation of diverse arylcyclopropanes, including valuable bicyclo[3.1.0] systems. This method was applied to a concise synthesis of lemborexant, a recently approved anti-insomnia drug.

Dehalogenation of functionalized alkyl halides in water at room temperature

Alkyl bromides and chlorides can be reduced to the corresponding hydrocarbons utilizing zinc in the presence of an amine additive. The process takes place in water at ambient temperatures, enabled by a commercially available designer surfactant. The reaction medium can be readily recycled, and the amount of organic solvent invested for product isolation is minimal, leading to very low E Factors. This journal is

Synergistic effect of additives on cyclopropanation of olefins

An efficient cyclopropanation of olefins with Zn(CH2I) 2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates,

PYRROLO SULFONAMIDE COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORGAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES

The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administrating these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo sulfonamide compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.

Cis-Dioxo-molybdenum(VI) Schiff base complexes: Synthesis, crystal structure and catalytic performance for homogeneous oxidation of olefins

The synthesis of two Mo(VI) tetradentate Schiff base complexes derived from 2,2′-dimethylpropylenediamine and aromatic aldehydes, (MoO 2{hnaphnptn} (1) and MoO2{salnptn(3-OMe)2} (2)) is reported. Full characterization of these complexes was accomplished with elemental analyses, spectroscopic studies (1H NMR, IR, and UV-Vis) and X-ray structure analysis. X-ray crystallography studies reveal that these complexes adopt a distorted octahedral six-coordinate configuration formed by tetradentate Schiff base ligand and two binding oxygen atoms. Catalytic performance of the prepared molybdenum complexes for oxidation of different olefins with tert-butyl hydroperoxide was evaluated. These complexes were found to be an efficient and selective catalyst for the homogeneous oxidation of various olefins. MoO2{salnptn(3-OMe)2} with a methoxy groups on the salicylidene ring of the ligand promote the effectiveness of the catalyst.

Preparation of a storable zinc carbenoid species and its application in cyclopropanation, chain extension, and [2,3]-sigmatropic rearrangement reactions

(Chemical Equation Presented) The formation of a new phosphate carbenoid (n-BuO)2P(O)OZnCH2I and its application in organozinc-mediated reactions is described. This carbenoid undergoes very slow degradation in solution and can be stored for several weeks at -20 °C. Its reactivity was tested with many representative alkenes and was determined to be a powerful cyclopropanating reagent, giving the corresponding cyclopropanes in 72-99% yield. The use of this carbenoid in the chain extension of 1,3-diketones and [2,3]-sigmatropic rearrangement reactions is also described. 2010 American Chemical Society.

Cyclopropanation of alkenes with CH2I2/Et3Al by the phase-vanishing method based on fluorous phase screen

Phase-vanishing (PV) method using perfluorohexanes as a screen phase was applied to cyclopropanation reactions with CH2I2/Et2Zn and CH2I2/Et3Al. When Et3Al was used as a carbenoid generator, the reaction proceeded smoothly and desired cyclopropane derivatives were obtained in high yield. The PV cyclopropanation took 2 or 3 days to complete, however, reduction of reaction time by a factor of 2-3 was also achieved by vigorous stirring after the bottom CH2I2 layer disappeared.

New copper(I) and silver(I) triazolato-complexes: Synthesis, reactivity and catalytic activity in olefin cyclopropanation

A new class of azolate ligands, deriving from the equimolar condensation of 3,5-diamino-1,2,4-triazole with salicylaldehyde (H3L1) and o-anisaldehyde (H3L2) was prepared. In their anionic form, these species act as bridging moieties upon coordination to Cu(I) and Ag(I), giving rise to the formation of dinuclear complexes with the ligand in the typical N,N′-exobidentate conformation. The copper derivative [Cu(H2L1)(CH3CN)]2 (1) showed attractive reactivity in the replacement of the labile acetonitrile molecules. In particular, it was possible to isolate a dinuclear copper(I)-carbonyl complex [Cu(H2L1)(CO)]2 (4), by substitution of the nitrile with carbon monoxide. Moreover, the reaction of 1 with ethyl diazoacetate (EDA) in CH2Cl2 afforded a mono-carbene product, as established by 13C NMR data. Finally, the copper derivative 1 proved to be a highly diastereoselective catalyst in olefin cyclopropanation in the presence of ethyl diazoacetate. In the case of internal alkenes a trans:cis ratio of up to 97:3 was reached. The X-ray structure of a dinuclear Ag(I) complex, namely [Ag(H2L1)(PPh3)]2 (3), obtained by reacting the polymeric [Ag(H2L1)]n (2), with triphenylphosphine, is also reported.