38768-08-0

Usage

Uses

Used in Pharmaceutical Industry:
Tropolone Tosylate is used as a purification agent for the preparation of L-piperidinecarboxylic acid, a compound with potential applications in the synthesis of pharmaceuticals. Its good adsorption effect ensures the efficient removal of impurities, resulting in a high-quality end product.

InChI:InChI=1/C14H12O4S/c1-11-7-9-12(10-8-11)19(16,17)18-14-6-4-2-3-5-13(14)15/h2-10H,1H3

Upstream product

• 533-75-5 2-hydroxy-2,4,6-cycloheptatrien-1-one 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 3786-66-1 2-amino-1,3-dicyanoazulene 
• 113548-32-6 2-<(R)-α-methylbenzylamino>tropone 
• 53526-98-0 2-<2-(m-tolyl)hydrazino>tropone 
• 53526-92-4 2-<2-(3-chlorophenyl)hydrazino>tropone 
• 118818-40-9 2-(N-amino-4-methoxyanilino)tropone 
• 2745-07-5 2-(2-phenylhydrazino)tropone 
• 53526-99-1 2-<2-(2-methoxyphenyl)hydrazino>tropone 
• 53526-97-9 2-<2-(o-tolyl)hydrazino>tropone 
• 107752-49-8 2-<2-(2-nitrophenyl)hydrazino>tropone 

Relevant academic research and scientific papers

Synthesis and conformational analysis of new troponyl aromatic amino acid

Synthetic peptides are in huge demand in expansion of potential peptide mimics, which may have improved or comparable function as natural one. With these concerns, phenyl bearing aromatic amino acids and peptides has extensively explored, because phenyl r

Novel azulene-based derivatives as potent multi-receptor tyrosine kinase inhibitors

A series of azulene-based derivatives were synthesized as potent inhibitors for receptor tyrosine kinases such as FMS-like tyrosine kinase 3 (FLT-3). Systematic side chain modification of prototype 1a was carried out through SAR studies. Analogue 22 was i

Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, c

Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.

The relationship between free radicals and acute or chronic inflammation has been well established. We have previously reported the significant antioxidant activity of the natural azulene derivatives chamazulene and guaiazulene. Furthermore, some syntheti

Radical and Ionic Reactions of Indolizin-1-ols: Synthesis of 3-Arylsulfanyl-, 3-(Tropon-2-yl)- And 3-(Tropolon-5-ylazo)-1-hydroxyindolizines from 3,3-Difluorocyclopropenes

An aerobic multicomponent reaction between monoalkyl-3,3-difluorocyclopropenes, pyridines, and arylthiols has been discovered to afford 3-arylsulfanyl-1-hydroxyindolizines. This reaction proceeds via intermediate C3-free indolizin-1-ols, easily forming free radicals in air. In the presence of arylthiols, potent radical traps, incorporation of arylsulfanyl substituent occurs at the C3 position of indolizin-1-ols by radical recombination. On the contrary, in an inert atmosphere, intermediate 1-hydroxyindolizines react with C- and N-electrophiles in a one-pot fashion. Novel, intensively colored 3-(tropon-2-yl)-indolizin-1-ols and high absorption coefficient 3-(tropolon-5-ylazo)-indolizin-1-ol dyes were synthesized in a multicomponent manner in 50-80% yields. The presence of an O-uncapped indolizin-1-ol moiety modulates the redox properties of the whole molecule, facilitating free radical formation, which is susceptible to further transformations. Three such examples were demonstrated: oxidative recyclization of 3-(2-hydroxyphenylsulfanyl)-indolizin-1-ol, auto-oxidation of substituted 3,3′-biindolizine-1,1′-diol, and diacetoxyiodobenzene (DAIB)-mediated dehydrogenation of 3-(tropolon-5-ylazo)-indolizin-1-ol. The latter reaction affords 3-((4,5-dioxocyclohepta-2,6-dien-1-ylidene)hydrazono)-3H-indolizin-4-ium-1-olate, a mesomeric betaine, strongly absorbing light on the borders of the visible range and showing a solvatochromic effect.

Synthesis and x-ray crystallography of chiral tropocoronands

The synthesis of several chiral tropocoronands (6 and 7) has been accomplished. These compounds have been shown to complex with various metals. Tropocoronands that have been synthesized include H2(TC-3,cyhex) through H2(TC-6,cyhex) (6) and H2 (TC-3,diphen) through H2(TC-6,diphen) (7). The route is short and the tropocoronands are easily purified by chromatography or recrystallization. Two other groups have been incorporated into tropocoronands, H2(TC-3,binap) (9) and H2(TC-6,pent) (10).

Structural Biology-Guided Design, Synthesis, and Biological Evaluation of Novel Insect Nicotinic Acetylcholine Receptor Orthosteric Modulators

The development of novel and safe insecticides remains an important need for a growing world population to protect crops and animal and human health. New chemotypes modulating the insect nicotinic acetylcholine receptors have been recently brought to the agricultural market, yet with limited understanding of their molecular interactions at their target receptor. Herein, we disclose the first crystal structures of these insecticides, namely, sulfoxaflor, flupyradifurone, triflumezopyrim, flupyrimin, and the experimental compound, dicloromezotiaz, in a double-mutated acetylcholine-binding protein which mimics the insect-ion-channel orthosteric site. Enabled by these findings, we discovered novel pharmacophores with a related mode of action, and we describe herein their design, synthesis, and biological evaluation.

BODIPY analogues: Synthesis and photophysical studies of difluoro boron complexes from 2-aminotropone scaffolds through: N, O -chelation

Boron-dipyrromethene (BODIPY) fluorophore derivatives were prepared from a Pyrromethene scaffold and di-fluoroboron. To add to the range of biocompatible fluorophores, this report describes the synthesis and photophysical studies of carboxylate-functionalized BODIPY analogues from natural products, Tropolone and α-amino acids, through N,O-chelation. The structure of a few derivatives was confirmed by single crystal X-ray studies. UV/fluorescence studies revealed their fluorescence behaviors in organic solvents with a quantum yield of ～0-15%, which varied based on the structure of amino acids. Further, electrochemical studies were accomplished by cyclic voltammetry, which confirm only one irreversible reduction reaction with Epc = -1.3 (V). Finally, their HOMO and LUMO molecular orbitals/energy differences were calculated from a theoretically (DFT) optimized structure, which also supported the role of amino group residues in the enhancement of the fluorescence. The glycinate derivative exhibited the greatest quantum yield compared to the other amino groups. Hence, 2-aminotropone containing BODIPY analogues are potential candidates for the development of various types of functionalized fluorophores as BODIPY analogues.

Syntheses and properties of linear π-conjugated molecules composed of 1-azaazulene and azulene

Two compounds, 6-(1-azaazulen-2-yl)ethynylazulene (8) and 6-(2-azulenyl)ethynylazulene (10), were synthesized using the Sonogashira-Hagihara cross-coupling reaction followed by decarboxylation with concentrated phosphoric acid. Compounds 8 and 10 were cha

Novel fluorophores: Syntheses and photophysical studies of boron-aminotroponimines

The syntheses and photophysical study of novel fluorescent boron-aminotroponimine complexes are described. The chemical structure of one of the boron complexes was confirmed by single crystal X-ray analysis, which shows the appearance of the distorted tetrahedral geometry at boron. The photophysical studies of these complexes revealed that the boron-aminotroponimines are fluorescent molecules with quantum yields ca. 0.17–0.28.