680190-96-9

Usage

Uses

Used in Organic Synthesis:
Tert-Butyl 4-ethynylbenzylcarbamate is used as a building block for the synthesis of various biologically active compounds. Its unique structure allows it to be a key component in creating pharmaceutical drugs and agrochemicals, contributing to the development of new and effective treatments and products.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, tert-Butyl 4-ethynylbenzylcarbamate is employed as a precursor in the design and synthesis of potential therapeutic agents. Its functional groups enable it to be modified and incorporated into diverse molecular frameworks, enhancing the discovery of novel drugs with improved pharmacological properties.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
Tert-Butyl 4-ethynylbenzylcarbamate is used as a reagent in Suzuki-Miyaura cross-coupling reactions, a class of palladium-catalyzed reactions that facilitate the formation of carbon-carbon bonds. Its participation in these reactions allows for the efficient construction of complex organic molecules, which are valuable in the synthesis of pharmaceuticals and other specialty chemicals.
Used in Sonogashira Coupling Reactions:
Additionally, tert-Butyl 4-ethynylbenzylcarbamate is utilized in Sonogashira coupling reactions, which are palladium-catalyzed reactions that form carbon-carbon bonds between sp and sp carbons. This reagent plays a crucial role in the synthesis of conjugated molecules, such as those found in organic materials and pharmaceutical agents, further expanding its applications in chemical research and development.

Upstream product

• 680190-94-7 1-azidomethyl-4-iodo-benzene 
• 68819-84-1 tert-butyl N-(4-bromobenzyl)carbamate 
• 26177-44-6 4-bromobenzylamine hydrochloride 
• 59528-27-7 p-iodobenzylamine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 16004-15-2 1-bromomethyl-4-iodobenzene 
• 189132-01-2 4-[(N-tert-butyloxycarbonylamino)methyl]iodobenzene 
• 39959-59-6 4-iodobenzyl amine 
• 680190-95-8 (4-trimethylsilylethyn-1-ylbenzyl)carbamic acid tert-butyl ester 

Downstream Products

• 1381949-73-0 ditert-butyl ((ethyne-1,2-diylbis(4,1-phenylene))bis(methylene))dicarbamate 
• 1482499-10-4 C₂₉H₂₆Fe₂N₂O₇S₂ 
• 197844-23-8 (4-ethynylphenyl)methanamine 
• 803704-45-2 4,4'-butadiynedibenzylamine 

Relevant academic research and scientific papers

The Delicate Balance of Preorganisation and Adaptability in Multiply Bonded Host–Guest Complexes

Rigidity and preorganisation are believed to be required for high affinity in multiply bonded supramolecular complexes as they help reduce the entropic penalty of the binding event. This comes at the price that such rigid complexes are sensitive to small geometric mismatches. In marked contrast, nature uses more flexible building blocks. Thus, one might consider putting the rigidity/high-affinity notion to the test. Multivalent crown/ammonium complexes are ideal for this purpose as the monovalent interaction is well understood. A series of divalent complexes with different spacer lengths and rigidities has thus been analysed to correlate chelate cooperativities and spacer properties. Too long spacers reduce chelate cooperativity compared to exactly matching ones. However, in contrast to expectation, flexible guests bind with chelate cooperativities clearly exceeding those of rigid structures. Flexible spacers adapt to small geometric host–guest mismatches. Spacer–spacer interactions help overcome the entropic penalty of conformational fixation during binding and a delicate balance of preorganisation and adaptability is at play in multivalent complexes.

Luminescence and Relaxometric Properties of Heteropolymetallic Metallostar Complexes with Selectively Incorporated Lanthanide(III) Ions

The synthesis and characterization of two diethylenetriaminepentaacetic acid (DTPA) based heteropolymetallic metallostar lanthanide complexes with the general formulas (GdL1)3Ln and (GdL2)3Ln are described. The

Exceptional poly(acrylic acid)-based artificial [FeFe]-hydrogenases for photocatalytic H2 production in water

Light, polymer, action: A set of water-soluble poly(acrylic acid) catalysts PAA-g-Fe2S2 containing {Fe2S2}, an [FeFe]-hydrogenase active-site mimic, is synthesized. This system, combined with CdSe quantum dots a

Degenerate molecular shuttles with flexible and rigid spacers

The preparation and dynamic behavior of degenerate rotaxane molecular shuttles are described in which a benzylic amide macrocycle moves back and forth between two naphthalimide-glycine units along a diphenylethyne spacer or an aliphatic spacer consisting of a C9, C12, or C 26 alkyl chain. Subtle differences in the 1H NMR spectra of the rotaxanes can be related to the presence of conformers in which the macrocycle interacts simultaneously with both glycines, especially in the case of the C9 spacer. The kinetic data of the shuttling behavior in the C26 rotaxane were obtained from dynamic NMR spectroscopy. The Eyring activation parameters were found to be ΔH? = 10 ± 1 kcal mol-1, ΔS? = -6.5 ± 2.0 cal mol-1 K-1, ΔG?298 = 11.9 ± 0.2 kcal mol-1. For the systems with the shorter spacers, the shuttling rates were higher. Also in the diphenylethyne, rotaxane shuttling is rapid on the NMR time scale, indicating that the rigid unit does not impose a large barrier to the translocation of the macrocycle.

Lacosamide isothiocyanate-based agents: Novel agents to target and identify lacosamide receptors

(R)-Lacosamide ((R)-2, (R)-N-benzyl 2-acetamido-3-methoxypropionamide) has recently gained regulatory approval for the treatment of partial-onset seizures in adults.Whole animal pharmacological studies have documented that (R)-2 function is unique. A robust strategy is advanced for the discovery of interacting proteins associated with function and toxicity of (R)-2 through the use of (R)-2 analogues, 3, which contain "affinity bait (AB)" and "chemical reporter (CR)" functional groups. In 3, covalent modification of the interacting proteins proceeds at the AB moiety, and detection or isolation of the selectively captured protein occurs through the bioorthogonal CR group upon reaction with an appropriate probe. We report the synthesis, pharmacological evaluation, and interrogation of the mouse soluble brain proteome using 3 where the AB group is an isothiocyanate moiety. One compound, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy) propionamide ((R)-9), exhibited excellent seizure protection in mice, and like (R)-2, anticonvulsant activity principally resided in the (R)-stereoisomer. Several proteins were preferentially labeled by (R)-9 compared with (S)-9, including collapsin response mediator protein 2. 2009 American Chemical Society.

N-[4-(Methylsulfonylamino)benzyl]thiourea analogues as vanilloid receptor antagonists: Analysis of structure-activity relationships for the 'C-Region'

We recently reported that N-(4-t-butylbenzyl)-N′-[4- (methylsulfonylamino)benzyl] thiourea (2) was a high affinity antagonist of the vanilloid receptor with a binding affinity of Ki=63 nM and an antagonism of Ki=53.9 nM in rat VR1 heterologously expressed in Chinese hamster ovary (CHO) cells (Mol. Pharmacol. 2002, 62, 947-956). In an effort to further improve binding affinity and antagonistic potency, we have modified the C-region of the lead 4-t-butylbenzyl group with diverse surrogates, such as araalkyl, alkyl, 4-alkynylbenzyl, indanyl, 3,3-diarylpropyl, 4-alkoxybenzyl, 4-substituted piperazine and piperidine. The lipophilic surrogates, arylalkyl and alkyl, conferred modest decreases in binding affinities and antagonistic potencies; the groups having heteroatoms resulted in dramatic decreases. Our findings indicate that 4-t-butylbenzyl is one of the most favorable groups for high receptor binding and potent antagonism to VR1 in this structural series.

Single-crystal-to-single-crystal polymerization of 4,4′- butadiynedibenzylammonium disorbate

Solid-state polymerization of 4,4′-butadiynedibenzylammonium disorbate was investigated. The quantitative polymer yield of the diene moieties was achieved under UV-, X-ray, and γ-ray irradiation, whereas the conversion of diyne moieties was low. X-ray cry