87630-35-1

Usage

Uses

Used in Organic Synthesis:
1-(Triisopropylsilyl)pyrrole is used as a reagent in perfluoroalkylation and Vilsmeier formylation reactions. It is employed for the preparation of ethyl 2-(2,4-dinitrophenylhydrazono)-3-[1-(triisopropylsilyl)pyrrol-2-yl]propanoate, a key intermediate in the synthesis of various organic compounds.
Used in Heterocyclic Chemistry:
TISP serves as a heterocyclic base for the synthesis of 3-nitropyrrole, which is an essential component in the preparation of 1-(2'-deoxy-β-D-ribofuranosyl)-3-nitropyrrole, a compound with potential applications in medicinal chemistry.
Used in Electrophilic Substitution Reactions:
1-(Triisopropylsilyl)pyrrole is used as a reactant in various electrophilic substitution reactions, specifically at the β-position, with different electrophilic reagents such as Br+, I+, and NO2+. This makes it a versatile building block for the synthesis of a wide range of heterocyclic compounds and organic molecules.

InChI:InChI=1/C13H25NSi/c1-11(2)15(12(3)4,13(5)6)14-9-7-8-10-14/h7-13H,1-6H3

Upstream product

• 109-97-7 pyrrole 
• 13154-24-0 triisopropylsilyl chloride 
• 16199-06-7 potassium pyrrolide 
• 87630-36-2 3-bromo-1-triisopropylsilanyl-1H-pyrrole 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 108030-46-2 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 
• 130408-79-6 α-bromo-1-(triisopropylsilyl)pyrrole 

Downstream Products

• 107407-80-7 ethyl pyrrolo[1,2-c]pyrimidine-3-carboxylate 
• 107384-68-9 1H-Pyrrolo<3,2-c>pyridin-6-carbonsaeure-ethylester 
• 5919-26-6 2-nitro-1H-pyrrole 
• 87630-39-5 1-(tri-isopropylsilyl)-3-nitropyrrole 
• 130408-83-2 3-chloro-1-(triisopropylsilyl)-1H-pyrrole 
• 130408-81-0 2-Chloro-1-triisopropylsilanyl-1H-pyrrole 
• 130408-84-3 2,3-dichloro-1-(triisopropylsilyl)pyrrole 
• 93362-53-9 2,3-dibromo-1-(triisopropylsilyl)pyrrole 
• 130408-80-9 2,4-Dibromo-1-triisopropylsilanyl-1H-pyrrole 
• 93362-54-0 3,4-dibromo-1--1H-pyrrole 
• 93362-20-0 2,3,4-tribromo-1-(triisopropylsilyl)pyrrole 
• 90971-77-0 3-benzoyl-1-(triisopropylsilyl)pyrrole 
• 27472-43-1 ethyl 1H-pyrrole-2-(α-oxo)acetate 
• 87630-37-3 ethyl 1-(triisopropylsilyl)-3-pyrrolylglyoxalate 

Relevant academic research and scientific papers

Cationic Polypyrrole Composites with Anionic Functional Molecules

Positively charged pyrroles incorporating the quaternized pyridine moiety, and , have been synthesized.The polymer of MPP (PMPP), cationic polypyrrole obtained by chemical polymerization and electropolymerization of MPP, is soluble in various polar solvents and displays anion-exchange ability.The amount of the incorporated anionic species in PMPP is ca. five times greater than that in polypyrrole because incorporation is through anodic doping and electrostatic binding with the pyridinium moiety.The PMPP composites with anionic metal complexes and anionic polymers provide films either by the casting method or by the dipping method.These films were also obtained by electropolymerization of MPP in the presence of the anionic functional molecules.The resulting composite-modified electrodes show clear electrochromism (EL) for PMPP/FeBPS and bright electrogenerated chemiluminescence (ECL) for PMPP/RuBPS, respectively.Excellent optical properties are achieved by incorporation of a large amount of the anionic functional molecules and therefore by suppression of undesired background absorption of the PMPP matrix.Another cationic polymer of PPP showed high conductivity (10-2 S cm-1) as well as high-density incorporation of anionic functional molecules.

Electrophilic fluorination of a highly functionalized pyrrole

Bromine-lithium exchange of 3-bromo-1-(triisopropylsilyl) pyrrole 6 followed by treatment with N-fluorobenzenesulfonimide gave the fluoropyrrole 8. Application of this methodology to the highly functionalized pyrrole 1 afforded the fluoropyrrole 4, which was found to be inaccessible by other approaches.

Regioselective syntheses of 2,3,4-tribromopyrrole and 2,3,5-tribromopyrrole

2,3,4-Tribromopyrrole (1) and 2,3,5-tribromopyrrole (2) were each synthesized from pyrrole. Spectral data and antifeedant effects for synthetic 1 and the antipredatory chemical defense compound of the marine hemichordate Saccoglossus kowalevskii were in agreement, confirming the structure of the deterrent natural product as 1. Spectral data for 2 differed from synthetic and natural 1.

Synthesis, biological evaluation, and docking studies of various β-substituted porphyrin conjugates embedded with N-containing heterocycles

A new methodology for the synthesis of some new β-porphyrin heterocyclic compounds containing nitrogen derivatives 10, 12, 13, 15, 17, 19, 21, 22, 25, 27, and 29 was screened for their cytotoxic activities. Both elemental and spectral analyses were used to confirm the structures of new compounds. Compounds 22, 27, and 21 exhibited very strong activity against the HepG2 cell line. Investigation of the binding between porphyrin 22 and the binding site of telomerase was performed by molecular docking.

Identification of the First Steps of the Electrochemical Polymerization of Pyrroles by Means of Fast Potential Step Techniques

The early stages of the electrochemical polymerization of three substituted pyrroles were investigated by means of fast double potential step chronoamperometry thanks to the use of electrodes in the micrometer diameter range.Systematic analysis of the reaction kinetics allowed the conclusion that, for all three pyrroles, the cation radicals, rather than the neutral radicals that would result from their deprotonation, are involved in the carbon-carbon bond forming process and that they couple between themselves rather than with the starting monomer.

Electron-transfer processes in 3,4-diferrocenylpyrroles: Insight into a missing piece of the polyferrocenyl-containing pyrroles family

3,4-Diiodo-1-(triisopropylsilyl)-1H-pyrrole (1), 3,4-diferrocenyl-1- (triisopropylsilyl)-1H-pyrrole (2), and 3,4-diferrocenyl-1H-pyrrole (3) were prepared and characterized using spectroscopic methods and X-ray crystallography. UV-vis spectra of 2 and 3 were correlated with their density functional theory (DFT)-calculated electronic structures as well as theoretically predicted by the time-dependent (TD) DFT-calculations vertical excitation energies. Redox properties of 2 and 3 were investigated using cyclic voltammetry, differential pulse voltammetry, and spectroelectrochemical approaches. Ferrocene-centered oxidation processes in 2 and 3 were found to be separated by ～180 and ～300 mV in DCM/TBAP and DCM/(NBu 4)[B(C6F5)4] systems, respectively. Stepwise spectroelectrochemical oxidation of 2 and 3 allowed us to obtain spectroscopic signatures of the mixed-valence [2]+ and [3] + cations. Hush analysis of the intervalence charge-transfer band in [2]+ and [3]+ is suggestive of class II (in Robin and Day classification) mixed-valence behavior. Electronic structures of neutral and spin-localized/delocalized single-electron oxidized mixed-valence cations of 2,5-di-, 3,4-di-, and 2,3,4,5-tetraferrocenylpyrroles were investigated by DFT calculations to resolve current uncertainties regarding the first oxidation process of tetraferrocenylpyrrole.

Identification, characterization, synthesis of major metabolites biotransformed from vonoprazan fumarate

A first synthetic research concerning four observed metabolites and their deuterium-labeled analogues of reflux esophagitis drug vonoprazan fumarate is reported. Among which the synthetic methods of three metabolites M ? I, M-III, M-IV-Sul, and four stable isotop labeled analogues M-I-d4, M-II-d4, M-III-d4, M-IV-Sul-d4 have not yet been reported before. The structures of these compounds were elucidated on the basis of MS and NMR spectroscopy.

4-Acyl Pyrrole Capped HDAC Inhibitors: A New Scaffold for Hybrid Inhibitors of BET Proteins and Histone Deacetylases as Antileukemia Drug Leads

Multitarget drugs are an emerging alternative to combination therapies. In three iterative cycles of design, synthesis, and biological evaluation, we developed a novel type of potent hybrid inhibitors of bromodomain, and extra-terminal (BET) proteins and histone deacetylases (HDACs) based on the BET inhibitor XD14 and well-established HDAC inhibitors. The most promising new hybrids, 49 and 61, displayed submicromolar inhibitory activity against HDAC1-3 and 6, and BRD4(1), and possess potent antileukemia activity. 49 induced apoptosis more effectively than the combination of ricolinostat and birabresib (1:1). The most balanced dual inhibitor, 61, induced significantly more apoptosis than the related control compounds 62 (no BRD4(1) affinity) and 63 (no HDAC inhibition) as well as the 1:1 combination of both. Additionally, 61 was well tolerated in an in vivo zebrafish toxicity model. Overall, our data suggest an advantage of dual HDAC/BET inhibitors over the combination of two single targeted compounds.

Synthesis of aminal-type Lilium candidum alkaloids and lilaline; determination of their relative configuration by the concerted use of NMR spectroscopy and DFT conformational analysis

We hereby report the synthesis of six racemic alkaloids isolated from Lilium candidum L. Their common structural feature is a five-membered lactam ring which is, in the case of the flavonoid alkaloid lilaline, attached to the molecule's aromatic core, while in the case of the other five compounds, it is connected to the nitrogen atom of a pyrrolinone ring by an aminal function. The syntheses of these natural products were achieved via Mannich-type alkylations through cyclic N-acyliminium ions as intermediates. Besides the synthesis, the so far unexplored stereochemistry of these natural products was determined by a combination of NMR-based proton–proton distance measurements and theoretical conformational analyses carried out at the DFT level.

Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity

Pseudomonads employ several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A-D, which have all been isolated from numerous Pseudomonad extracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth in Pseudomonads.