97023-66-0

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 19956-78-6 diphenylsulfonium 2-ethoxy-2-oxoethylide 
• 637-50-3 1-phenylpropene 

Downstream Products

• 24581-87-1 (1R*,2S*,3S*)-2-methyl-3-phenylcyclopropane-1-carboxylic acid 
• 24581-87-1 (1R*,2R*,3S*)-2-methyl-3-phenylcyclopropane-1-carboxylic acid 
• 24581-87-1 (1S*,2S*,3S*)-2-methyl-3-phenylcyclopropane-1-carboxylic acid 

Relevant academic research and scientific papers

Synthesis and evaluation of ruthenium catalysts containing diamine-based ligands in olefin cyclopropanation

Ruthenium complexes with N-(p-toluenesulfonyl)-diamine ligands were found to be efficient in the catalytic cyclopropanation reaction of olefins with alkyl diazoacetate.

Catalytic cyclopropanation, antimicrobial, and DFT properties of some chelated transition metal(II) complexes

Transition Metal (II) complexes of general formula [MII(NH2C2H4NH2)3][B(C6F5)4]2 (1-6), where (M= Mn, Fe, Co, Ni, Cu, Zn) have been synthesized and characterized in the solid state and in solution using elemental, thermogravimetric analysis, EPR, 11B-NMR and IR spectroscopy. All complexes were used as catalysts for the cyclopropanation reaction with a variety of olefins. Excellent yields up to 93% were obtained using complex 5. All prepared complexes were used as anti-bacterial agents against different types of bacteria (Gram-negative and Gram-positive), and as anti-fungal agents. Complex 6 showed the highest activity with MIC value of 8 μg/mL against Staphylococcus aureus (Gram-positive bacteria), and of 16 μg/mL against candida albicans. To get more insights into their structural features, molecular geometries of all prepared complexes were fully optimized using density functional theory calculations at the M06-2X/6-311+G** level of theory.

Structure-activity studies on N-Substituted tranylcypromine derivatives lead to selective inhibitors of lysine specific demethylase 1 (LSD1) and potent inducers of leukemic cell differentiation

FAD-dependent lysine-specific demethylase 1 (LSD1) is overexpressed or deregulated in many cancers such as AML and prostate cancer and hence is a promising anticancer target with first inhibitors in clinical trials. Clinical candidates are N-substituted derivatives of the dual LSD1-/monoamine oxidase-inhibitor tranylcypromine (2-PCPA) with a basic amine function in the N-substituent. These derivatives are selective over monoamine oxidases. So far, only very limited information on structure-activity studies about this important class of LSD1 inhibitors is published in peer reviewed journals. Here, we show that N-substituted 2-PCPA derivatives without a basic function or even a polar group are still potent inhibitors of LSD1 in vitro and effectively inhibit colony formation of leukemic cells in culture. Yet, these lipophilic inhibitors also block the structurally related monoamine oxidases (MAO-A and MAO-B), which may be of interest for the treatment of neurodegenerative disorders, but this property is undesired for applications in cancer treatment. The introduction of a polar, non-basic function led to optimized structures that retain potent LSD1 inhibitors but exhibit selectivity over MAOs and are highly potent in the suppression of colony formation of cultured leukemic cells. Cellular target engagement is shown via a Cellular Thermal Shift Assay (CETSA) for LSD1.

Generation and Reactivity of Electron-Rich Carbenes on the Surface of Catalytic Gold Nanoparticles

The reactive nature of carbenes can be modulated, and ultimately reversed, by receiving additional electron density from a metal. Here, it is shown that Au nanoparticles (NPs) generate an electron-rich carbene on surface after transferring electron density to the carbonyl group of an in situ activated diazoacetate, as assessed by Fourier transformed infrared (FT-IR) spectroscopy, magic angle spinning nuclear magnetic resonance (MAS NMR), and Raman spectroscopy. Density functional theory (DFT) calculations support the observed experimental values and unveil the participation of at least three different Au atoms during carbene stabilization. The surface stabilized carbene shows an extraordinary stability against nucleophiles and reacts with electrophiles to give new products. These findings showcase the ability of catalytic Au NPs to inject electron density in energetically high but symmetrically allowed valence orbitals of sluggish molecules.

ARTIFICIAL METALLOENZYMES CONTAINING NOBLE METAL-PORPHYRINS

The present invention is drawn to artificial metalloenzymes for use in cyclopropanation reactions, amination and C—H insertion.

A RuII-N-heterocyclic carbene (NHC) complex from metal-metal singly bonded diruthenium(I) precursor: Synthesis, structure and catalytic evaluation

A mononuclear Ru(II)-N-heterocyclic carbene (NHC) complex [Ru II(CO)2(κ2C,N-BIN)(H2O)Br] [OTf] (OTf = trifluoromethane sulphonate) (1) has been synthesized in high-yield by the oxidative cleavage of the metal-metal singly-bonded diruthenium(I) precursor [Ru2(CO)4(CH3CN)6(OTf) 2] with 1,8-naphthyridine functionalized NHC precursor 1-benzyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazolium bromide (BIN·HBr) at room temperature. Compound 1 catalyzes transfer hydrogenation of ketones to alcohols, and carbene-transfer from ethyl diazoacetate to a variety of substrates. It is shown to be an excellent catalyst for the insertion of carbene into the O-H and N-H bonds of alcohols and amines.

From homogeneously to heterogeneously catalyzed cyclopropanation reactions: New polymeric membranes embedding cobalt chiral schiff base complexes

In this paper we report the preparation of catalytic polymeric membranes having the complex [(N,N′-bis(3-tert-butyl-5-(heptadecafluorooctyl)salicylidene)-trans-1,2-cyclohexanediamine)Co] embedded into Hyflon AD60X, PES and PSf and their use in the cyclopr

Stabilization and recovery of gold catalysts in the cyclopropanation of alkenes within ionic liquids

Au(I) and Au(III) salts (NaAuCl4 and KAuCN2 respectively) were found to be active catalysts for the cyclopropanation of alkenes with ethyldiazoacetate, in many cases affording high yields of cyclopropanecarboxylates. But these gold s

Rhodium acetate dimer immobilized in 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid: A novel and recyclable catalytic system for the cyclopropanation of alkenes

Alkenes undergo smooth cyclopropanation with ethyl diazoacetate using a catalytic amount of rhodium acetate dimer, Rh2(OAc)4, immobilized in the air- and moisture-stable 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid, [

Strong electronic effects in the cis-selective asymmetric cyclopropanation of olefins catalyzed by [RuCl(PNNP)]+

The cationic [RuCl(PNNP)]+ catalysts containing tetradentate ligands with a P2N2 donor set (PNNP) show strong electronic effects in the cyclopropanation of para-substituted styrenes. The reactivity trend confirms that the carbene transfer to the olefin has electrophilic character. Linear free-energy relationships are observed for the relative reactivity, the cis/trans selectivity, and for the enantioselectivity (of the cis-cyclopropane). The linear correlation between log (kX/kH) and σ shows a large value of ρ (-2.4), which is indicative of significant charge buildup in the transition state of the carbene transfer to the olefin. All the relevant parameters (reactivity, diastereoselectivity, and enantioselectivity) increase with the increasing electron density at the C=C bond. To define the scope of the [RuCl(PNNP)]+ catalysts, 1- and 2-substituted styrenes, and oct-1-ene were also investigated.