5861-31-4

Upstream product

• 100-42-5 styrene 
• 6832-16-2 methyl diazoacetate 
• 186581-53-3 diazomethane 
• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 
• 67-56-1 methanol 
• 23020-15-7 (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 103-26-4 Methyl cinnamate 
• 292638-85-8 acrylic acid methyl ester 
• 100-39-0 benzyl bromide 
• 97-71-2 ethyl (S,S)-2-phenylcyclopropane-1-carboxylate 
• 97-71-2 ethyl (1S,2R)-2-phenylcyclopropylcarboxylate 
• 48126-51-8 (1R,2S)-2-phenylcyclopropane-1-carboxylic acid 
• 75-09-2 dichloromethane 
• 6482-26-4 methyl dibromoacetate 

Downstream Products

• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 53403-04-6 (+)-(1S,2S)-1-methyl-2-phenylcyclopropane 
• 110659-49-9 (+)-(1'S,2'S)-2-(2'-methylcyclopropyl)aniline 
• 110659-48-8 (1'S,2'S)-1-(2'-methylcyclopropyl)-2-nitrobenzene 
• 29667-46-7 (1S,2R)-2-phenylcyclopropylmethanol 
• 29667-47-8 (+)-(1S,2R)-1-methyl-2-phenylcyclopropane 
• 110659-53-5 (+)-(1'R,2'S)-2-(2'-methylcyclopropyl)aniline 
• 110659-52-4 (1'R,2'S)-1-(2'-methylcyclopropyl)-2-nitrobenzene 
• 14561-40-1 2-phenyl-cyclopropanecarboxylic acid hydrazide 
• 79981-48-9 trans-(3-phenylcyclopropyl)methanol 
• 13279-88-4 racemic trans-2-methoxycarbonylcyclopropanecarboxylic acid 
• 67528-62-5 cis-methyl 2-phenylcyclopropane-1-carboxylate 
• 34271-31-3 trans-2-phenylcyclopropanecarbaldehyde 
• 56434-66-3 1-Methyl-c-2-phenyl-r-1-cyclopropancarbonsaeure-methylester 

Relevant academic research and scientific papers

Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters

Diacids are important monomers in the polymer industry to construct valuable materials. Dicarboxylation of unsaturated bonds, such as alkenes and alkynes, with CO2 has been demonstrated as a promising synthetic method. However, dicarboxylation of C-C single bonds with CO2 has rarely been investigated. Herein we report a novel electrochemical ring-opening dicarboxylation of C-C single bonds in strained rings with CO2. Structurally diverse glutaric acid and adipic acid derivatives were synthesized from substituted cyclopropanes and cyclobutanes in moderate to high yields. In contrast to oxidative ring openings, this is also the first realization of an electroreductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggested that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of the products. Furthermore, we conducted polymerization of the corresponding diesters with diols to obtain a potential UV-shielding material with a self-healing function and a fluorine-containing polyester, whose performance tests showed promising applications.

Boronic Acid-Mediated Photocatalysis Enables the Intramolecular Hydroacylation of Olefins Using Carboxylic Acids

An intramolecular hydroacylation of olefins using carboxylic acids (CAs) has been developed. With the aid of a boronic acid, CAs can be used as acyl-radical precursors in catalytic photoredox reactions driven by visible light. The CAs are easily converted into their corresponding cyclic ketones without the need to use any stoichiometric activating reagents. Mechanistic studies implied that the formation of an “ate” complex from the CA and boronic acid is crucial for the generation of the acyl radical equivalent from the unreactive carboxy group.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound

The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C-H activation, O-H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.

Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction

The potential of [PAIM][NTf2]/BMIM-ILs as a base/solvent in the Corey-Chaykovsky reaction is demonstrated by the facile synthesis of libraries of functionalized cyclopropanes from enones and oxiranes from aldehydes and ketones, at room temperature in respectable isolated yields. To demonstrate their application, the synthesized epoxides were employed as substrates for the synthesis of a library of 2,3-disubstituted quinolines, using [BMIM(SO3H)][OTf]/[BMIM][PF6] as a catalyst/solvent. The potential for recycling/reuse of the IL solvents was also explored.

Donor-Acceptor Bicyclopropyls as 1,6-Zwitterionic Intermediates: Synthesis and Reactions with 4-Phenyl-1,2,4-triazoline-3,5-dione and Terminal Acetylenes

The bicyclopropyl system activated by incorporation of donor and acceptor groups in the presence of Lewis acids was used as a synthetic equivalent of 1,6-zwitterions. Opening of both cyclopropane rings in 2′-aryl-1,1′-bicyclopropyl-2,2-dicarboxylates (D-A bicyclopropyl, ABCDs) in the presence of GaI3 + Bu4N+GaI4- results in 5-iodo-5-arylpent-2-enylmalonates as products of HI formal 1,6-addition to the bicyclopropyl system. The use of GaCl3 or GaBr3 as a Lewis acid and terminal aryl or alkyl acetylenes as 1,6-zwitterion interceptors allows the alkyl substituent to be grown to give the corresponding acyclic 7-chloro(bromo)-hepta-2,6-dienylmalonates. The reaction of ABCDs with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) catalyzed by Yb(OTf)3 also results in the opening of both cyclopropane rings. The reaction products are tetrahydropyridazine derivatives - (7,9-dioxo-1,6,8-triazabicyclo[4.3.0]non-3-en-2-ylmethyl)malonates - containing one more PTAD moiety in the malonyl group.

ARYL CYCLOPROPYL-AMINO-ISOQUINOLINYL AMIDE COMPOUNDS

Provided herein are arylcyclopropyl amino-isoquinoline amide compounds. In particular, the disclosure provides compounds that affect the function of kinases in a cell and that are useful as therapeutic agents or with therapeutic agents. The compounds of t

Catalytic Hydrogenolysis of Enantioenriched Donor–Acceptor Cyclopropanes Using H2 and Palladium on Charcoal

The hydrogenolysis of enantioenriched donor–acceptor (D–A) cyclopropanes using H2 (1 atm) and a catalytic amount of palladium on charcoal gave trans-α-alkoxycarbonyl-β-benzyl-γ-lactones or β-substituted γ-aryl-α,α-diesters with high enantiomeric excess. The reaction was also used as a key step in the asymmetric total synthesis of yatein with high ee and excellent dr. This demonstrates the utility of this new protocol for the asymmetric synthesis of trans-α,β-disubstituted γ-butyrolactones. D–A cyclopropanes containing electron-withdrawing groups at the β-position were not susceptible to hydrogenolysis under these conditions. The reductive ring-opening of a D–A cyclopropane using D2 instead of H2 generated the corresponding monodeuterated product.

Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

A configurationally simple and robust semibatch apparatus for the in situ on-demand generation of anhydrous solutions of diazomethane (CH2N2) avoiding distillation methods is presented. Diazomethane is produced by base-mediated decomposition of commercially available Diazald within a semipermeable Teflon AF-2400 tubing and subsequently selectively separated from the tubing into a solvent- and substrate-filled flask (tube-in-flask reactor). Reactions with CH2N2 can therefore be performed directly in the flask without dangerous and labor-intensive purification operations or exposure of the operator to CH2N2. The reactor has been employed for the methylation of carboxylic acids, the synthesis of α-chloro ketones and pyrazoles, and palladium-catalyzed cyclopropanation reactions on laboratory scale. The implementation of in-line FTIR technology allowed monitoring of the CH2N2 generation and its consumption. In addition, larger scales (1.8 g diazomethane per hour) could be obtained via parallelization (numbering up) by simply wrapping several membrane tubings into the flask.

Synthesis of a novel C2-symmetric bis-oxazoline (=bis[4,5-dihydrooxazole]) and its application as chiral ligand in asymmetric transition metal catalysis

The new C2-symmetric bis-oxazoline (=bis[4,5-dihydrooxazole]) 2 with a chiral trans-(2R,3R)-2,3-bis(3,5-diphenylphenyl)cyclopropylidene (=trans-(2R,3R)-2,3-bis([1,1′: 3′,1″-terphenyl]-5′-yl) cyclopropylidene) backbone was efficiently synthesized (Scheme). All synthetic steps were easy to perform and led to the desired product in good overall yields. Compound 2 was tested and compared as ligand in several enantioselective catalytic reactions such as palladium(0)-catalyzed enantioselective allylic alkylations and copper(I)-catalyzed enantioselective cyclopropanations and aziridinations. Copyright