22003-17-4

Usage

Uses

Used in Pharmaceutical Industry:
(Phenylmethyl)-carbamic acid phenyl ester is used as an intermediate for the synthesis of various pharmaceuticals, contributing to the development of new medications and therapies.
Used in Pesticide Industry:
(Phenylmethyl)-carbamic acid phenyl ester is also utilized as a pesticide, highlighting its application in agriculture to protect crops from pests and ensure a stable food supply.
Used as a Chemical Reaction Inhibitor:
(Phenylmethyl)-carbamic acid phenyl ester serves as an inhibitor in various chemical reactions, playing a crucial role in controlling the rate and progress of these processes.
Used as a Solvent in Different Applications:
(Phenylmethyl)-carbamic acid phenyl ester is employed as a solvent in a range of applications, demonstrating its versatility and utility across different industries and processes.

InChI:InChI=1/C14H13NO2/c16-14(17-13-9-5-2-6-10-13)15-11-12-7-3-1-4-8-12/h1-10H,11H2,(H,15,16)

Upstream product

• 3173-56-6 benzyl isothiocyanate 
• 108-95-2 phenol 
• 1885-14-9 phenyl chloroformate 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 
• 102-09-0 bis(phenyl) carbonate 
• 10229-60-4 Z-benzaldehyde O-benzyloxime 
• 4383-24-8 N,O-dibenzylhydroxylamine 
• 17175-11-0 phenyl O‐(4‐nitrophenyl) carbonate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 65263-72-1 N-benzyl O-methyl thiocarbamate 
• 5555-82-8 N-(phenylmethoxy)-N-bnzylphenoxycarboxamide 
• 622-46-8 carbamic acid phenyl ester 

Downstream Products

• 1987-58-2 N-[[(phenylmethyl)amino]carbonyl]-p-toluenesulfonamide 
• 47037-01-4 N-(benzylcarbamoyl)benzenesulfonamide 
• 51327-43-6 N-(benzylcarbamoyl)-4-chlorobenzenesulfonamide 
• 31348-34-2 N-(benzylcarbamoyl)-4-bromobenzenesulfonamide 
• 13143-28-7 1-benzyl-3-(m-tolyl)urea 
• 5436-83-9 N-benzyl-4-methylbenzamide 
• 1086764-86-4 4-[(3-benzylureido)methyl]benzoic acid 
• 15667-57-9 6-(N'-benzyl-ureido)-hexanoic acid 
• 57965-06-7 ethyl 2-(benzylcarbamoyl)hydrazine-1-carboxylate 
• 2221-11-6 3,5-dibenzyltetrahydro-1H-imidazole-2,4-dione 
• 34658-65-6 3-benzyl-5-phenylimidazolidine-2,4-dione 
• 2301-40-8 3-benzylhydantoin 
• 2301-36-2 3-benzyl-5-methylimidazolidine-2,4-dione 
• 148149-21-7 1-isoquinolinecarboxylic acid benzylamide 

Relevant academic research and scientific papers

A practical synthesis of carbamates using an 'in-situ' generated polymer-supported chloroformate

A versatile method for the synthesis of carbamates from an 'in-situ' generated polymer-supported chloroformate resin is presented. BTC (bis-trichloromethyl carbonate) is used as phosgene equivalent to afford a supported chloroformate, which, by sequential 'one-pot' reaction with a variety of alcohols and amines, furnishes the corresponding carbamates in high yields and purities. A versatile method for the synthesis of carbamates from an 'in-situ' generated polymer-supported chloroformate resin is presented. BTC (bis-trichloromethyl carbonate) is used as phosgene equivalent to afford a supported chloroformate, which, by sequential 'one-pot' reaction with a variety of alcohols and amines, furnishes the corresponding carbamates in high yields and purities.

3-(dimethylaminomethyl) piperidine-4-alcohol derivative as well as preparation method and pharmaceutical application thereof

The present invention provides compounds of formula (FWBF) or pharmaceutically acceptable salts thereof, in which the substituents are as defined in the specification, as well as a preparation method and pharmaceutical use thereof.

Design, synthesis, and biological activity of novel semicarbazones as potent Ryanodine receptor1 inhibitors of Alzheimer's disease

Ryanodine receptors (RyRs) are important ligand-gated Ca2+ channels; their excessive activation leads to Ca2+ leakage in the sarcoplasmic reticulum that may cause neurological diseases. In this study, three series of novel potent RyR1 inhibitors based on dantrolene and bearing semicarbazone and imidazolyl moieties were designed and synthesized, and their biological activity was evaluated. Using a single-cell calcium imaging method, the calcium overload inhibitory activities of 26 target compounds were tested in the R614C cell line, using dantrolene as a positive control. The preliminary investigation showed that compound 12a suppressed Ca2+ release as evidenced by store overload-induced Ca2+release (SOICR) (31.5 ± 0.1%, 77.2 ± 0.1%, 93.7 ± 0.2%) at 0.1 μM, 3 μM and 10 μM, respectively. Docking simulation results showed that compound 12a could bind at the active site of the RyR1 protein. The Morris water-maze test showed that compound 12a significantly improved the cognitive behavior of AD-model mice. Further studies on the structural optimization of this series of derivatives are currently underway in our laboratory.

Discovery of 3-((dimethylamino)methyl)-4-hydroxy-4-(3-methoxyphenyl)-N-phenylpiperidine-1-carboxamide as novel potent analgesic

Management of moderate to severe pain by clinically used opioid analgesics is associated with a plethora of side effects. Despite many efforts have been dedicated to reduce undesirable side effects, moderate progress has been made. In this work, starting from Tramadol, a series of 3-((dimethylamino)methyl)-4-hydroxy-4-(3-methoxyphenyl)piperidine-1-carboxamide derivatives were designed and synthesized, and their in vitro and in vivo activities were evaluated. Our campaign afforded selective μ opioid receptor (MOR) ligand 2a (KiMOR: 7.3 ± 0.5 nM; KiDOR: 849.4 ± 96.6 nM; KiKOR: 49.1 ± 6.9 nM) as potent analgesic with ED50 of 3.1 mg/kg in 55 °C hot plate model. Its antinociception effect was blocked by opioid antagonist naloxone. High binding affinity toward MOR of compound 2a was associated with water bridge, salt bridge, hydrogen bond and hydrophobic interaction with MOR. The high selectivity of compound 2a for MOR over δ opioid receptor (DOR) and κ opioid receptor (KOR) was due to steric hindrance of compound 2a with DOR and KOR. 2a, a compound with novel scaffold, could serve as a lead for the development of novel opioid ligands.

Monofunctionalized Bambus[6]urils and Their Conjugates with Crown Ethers for Liquid-Liquid Extraction of Inorganic Salts

Bambusurils are a growing family of macrocyclic anion receptors. In this Letter, we present the first syntheses of monofunctionalized bambusurils and their use for the preparation of heteroditopic bambusuril-crown ether conjugates suitable for the extraction of ion pairs from water to chloroform.

Investigations into the carbonic anhydrase inhibition of COS-releasing donor core motifs

Carbonyl sulfide (COS) releasing scaffolds are gaining popularity as hydrogen sulfide (H2S) donors through exploitation of the carbonic anhydrase (CA)-mediated hydrolysis of COS to H2S. The majority of compounds in this emerging class of donors undergo triggerable decomposition (often referred to as self-immolation) to release COS, and a handful of different COS-releasing structures have been reported. One benefit of this donation strategy is that numerous caged COS-containing core motifs are possible and are poised for development into self-immolative COS/H2S donors. Because the intermediate release of COS en route to H2S donation requires CA, it is important that the COS donor motifs do not inhibit CA directly. In this work, we investigate the cytotoxicity and CA inhibition properties of different caged COS donor cores, as well as caged CO2 and CS2 motifs and non-self-immolative control compounds. None of the compounds investigated exhibited significant cytotoxicity or enhanced cell proliferation at concentrations up to 100 μM in A549 cells, but we identified four core structures that function as CA inhibitors, thus providing a roadmap for the future development of self-immolative COS/H2S donor motifs.

Spontaneous and direct transformation of N,O-diaryl carbamates into N,N′-diarylureas

We have discovered a spontaneous reaction of N,O-diaryl carbamates to afford symmetrical N,N′-diarylureas. Optimization of the conditions indicated that N,N-dimethylformamide (DMF) was the best solvent and triethylamine (Et3N) was the best additive for this transformation. The reaction requires the presence of aryl groups on the nitrogen and oxygen atoms of carbamates. Substrates bearing an electron-donating methoxy group on either of the aryl groups reacted slowly under these conditions.

6,7-DIHYDRO-4H-PYRAZOLO[1,5-A]PYRAZINE AND 6,7-DIHYDRO-4H-TRIAZOLO[1,5-A]PYRAZINE COMPOUNDS FOR THE TREATMENT OF INFECTIOUS DISEASES

The present invention relates to compounds of the formula (I), or pharmaceutically acceptable salts, enantiomer or diastereomer thereof, wherein R1 to R4 and Q are as described above. The compounds may be useful for the treatment or prophylaxis of hepatitis B virus infection.

Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.

A facile synthesis of sulfonylureas: Via water assisted preparation of carbamates

A novel and simple approach to the synthesis of sulfonylureas has been reported. It involved the reaction of various amines with diphenyl carbonate to yield the corresponding carbamates, which subsequently reacted with different sulphonamides to produce different sulfonylureas in excellent yields. The first reaction of diphenyl carbonate with amines was carried out in aqueous:organic (H2O:THF, 90:10) medium at room temperature to produce carbamates that paved a straightforward route to sulfonylureas after reaction with sulfonamides. The above process avoided traditional multistep protocols and the use of hazardous, irritant, toxic and moisture sensitive reagents such as phosgene, isocyanates and/or chloroformates.