14649-03-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1-Phenylethyl isocyanate is used as a chiral derivatizing agent for the resolution of enantiomers, which is crucial in the development of drugs with improved efficacy and reduced side effects.
Used in Cancer Prevention and Treatment:
(S)-(-)-1-Phenylethyl isocyanate is used as a potential cancer preventive and therapeutic agent for lung cancer and esophageal cancer. It works by inhibiting cell proliferation and inducing apoptosis, thereby helping to prevent the growth and spread of cancer cells.
Used in Fine Chemical Industry:
(S)-(-)-1-Phenylethyl isocyanate is used as a fine chemical intermediate in the synthesis of various compounds, contributing to the development of new materials and products in the chemical industry.

Purification Methods

Purify the isocyanates by fractional distillation under a vacuum. With ammonia

InChI:InChI=1/C9H9NO/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3/t8-/m0/s1

Upstream product

• 1623-51-4 α-Phenethylcarbamidsaeureethylester 
• 3315-16-0 silver cyanate 
• 585-71-7 (1-bromoethyl)benzne 
• 100-42-5 styrene 
• 75-13-8 isocyanic acid 
• 618-36-0 rac-methylbenzylamine 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 
• 98-85-1 1-Phenylethanol 
• 39139-87-2 tetrabutylammonium isocyanate 
• 14856-75-8 1-phenyl-1-trimethylsilyloxyethane 
• 492-37-5 hydratropic acid 
• 105966-39-0 2-(1-phenylethoxy)-tetrahydro-2H-pyran 
• 208924-64-5 (±)-N-hydroxy-2-phenylpropanamide 

Downstream Products

• 101260-94-0 (1-phenyl-ethyl)-carbamic acid-(2-diethylamino-ethyl ester) 
• 101174-10-1 6β-[3-((Ξ)-1-phenyl-ethyl)-ureido]-penicillanic acid 
• 40589-84-2 1-phenethyl urea 
• 80490-87-5 Piperazine-1,4-dicarboxylic acid bis-[(1-phenyl-ethyl)-amide] 
• 88235-71-6 5-Hydroxyamino-3,4,4-trimethyl-1-(1-phenyl-ethyl)-imidazolidin-2-one 
• 121060-83-1 1-[2-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-4-chloro-phenyl]-3-(1-phenyl-ethyl)-urea 
• 143164-06-1 ((S)-1-Phenyl-ethyl)-carbamic acid (6S,7S)-5,5-dimethyl-7-(2-oxo-piperidin-1-yl)-6,7-dihydro-5H-thieno[3,2-b]pyran-6-yl ester 
• 147169-48-0 (R,S)-N-(tert-butyloxycarbonyl)-α-methylbenzylamine 

Relevant academic research and scientific papers

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/[n-Bu4N]OCN as a useful system for the efficient conversion of tetrahydropyranyl (THP) ethers to the corresponding alkyl isocyanates

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium cyanate was used as an efficient system for the conversion of tetrahydropyranyl ethers to the corresponding alkyl isocyanates. Taylor & Francis Group, LLC.

Cocrystallization of Chiral N7,N16-bis (S-1-Phenylethyl)-1,4,10,13-Tetraoxo-7,16-Diazacyclooctadecane-7,16-Dicarboxamide with Hydrochlorides of Methyl Ethers of Leucine and Valine Enantiomers

An attempt to co-crystallize N7,N16-bis(S-1-phenylethyl)-1,4,10,13-tetraoxo-7,16-diazacyclooctadecane-7,16-dicarboxamide (1) with hydrochlorides of methyl ethers (HCMEs) of L- and D-valine and also L- and D-leucine results in separate crystallization of diazacrown-ether 1 (or its monohydrate 1·H2O) and HCMEs of respective α-amino acids. Crystal structures of D-leucine 1·H2O (1) and HCME (2) compounds, which were not described previously, are solved by single crystal X-ray diffraction.

A new and convenient method of generating alkyl isocyanates from alcohols, thiols and trimethylsilyl ethers using triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone/Bu4NOCN

Alkyl isocyanates are prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with triphenylphosphine/2,3-dichloro- 5,6-dicyanobenzoquinone/ Bu4NOCN in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl isocyanates in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers. Georg Thieme Verlag Stuttgart.

Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates

We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.

Benzylic C-H isocyanation/amine coupling sequence enabling high-throughput synthesis of pharmaceutically relevant ureas

C(sp3)-H functionalization methods provide an ideal synthetic platform for medicinal chemistry; however, such methods are often constrained by practical limitations. The present study outlines a C(sp3)-H isocyanation protocol that enables the synthesis of diverse, pharmaceutically relevant benzylic ureas in high-throughput format. The operationally simple C-H isocyanation method shows high site selectivity and good functional group tolerance, and uses commercially available catalyst components and reagents [CuOAc, 2,2′-bis(oxazoline) ligand, (trimethylsilyl)isocyanate, andN-fluorobenzenesulfonimide]. The isocyanate products may be used without isolation or purification in a subsequent coupling step with primary and secondary amines to afford hundreds of diverse ureas. These results provide a template for implementation of C-H functionalization/cross-coupling in drug discovery.

CARBAMATE DERIVATIVES AND USES THEREOF

The present disclosure relates to compounds of Formula (I): and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.

Amide compound, pharmaceutical composition, preparation method and application thereof

The invention provides an amide compound, a pharmaceutical composition, a preparation method and application thereof and belongs to the field of medicine. Structure of the amide compound is shown as aformula I. The preparation method includes: in an alkaline condition and in an organic solvent, allowing a compound I and a compound II to be in condensation reaction. The amide compound or pharmaceutically acceptable salt thereof have long-acting sensory and/or motion blocking activity, can be used for preparing long-acting local anesthetic or analgesic and is long in efficacy lasting time, little side effect and high in medication safety.

Alkyl Isocyanates via Manganese-Catalyzed C-H Activation for the Preparation of Substituted Ureas

Organic isocyanates are versatile intermediates that provide access to a wide range of functionalities. In this work, we have developed the first synthetic method for preparing aliphatic isocyanates via direct C-H activation. This method proceeds efficiently at room temperature and can be applied to functionalize secondary, tertiary, and benzylic C-H bonds with good yields and functional group compatibility. Moreover, the isocyanate products can be readily converted to substituted ureas without isolation, demonstrating the synthetic potential of the method. To study the reaction mechanism, we have synthesized and characterized a rare MnIV-NCO intermediate and demonstrated its ability to transfer the isocyanate moiety to alkyl radicals. Using EPR spectroscopy, we have directly observed a MnIV intermediate under catalytic conditions. Isocyanation of celestolide with a chiral manganese salen catalyst followed by trapping with aniline afforded the urea product in 51% enantiomeric excess. This represents the only example of an asymmetric synthesis of an organic urea via C-H activation. When combined with our DFT calculations, these results clearly demonstrate that the C-NCO bond was formed through capture of a substrate radical by a MnIV-NCO intermediate.

N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement

An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger-aza-Wittig reaction

A fast and efficient protocol for the synthesis of N,N'-disubstituted urea derivatives from alkyl halides and primary or secondary amines has been developed. The synthetic pathway combines nucleophilic substitutions and a Staudinger-aza-Wittig reaction in the presence of polymer-bound diphenylphosphine under 14 bar of CO2 pressure and has been performed in a one-pot two-step process. The protocol has been optimized under microwave irradiation and the scale-up experiment has been conducted under conventional conditions in a Parr reactor. The final compounds were isolated after simple filtration in almost quantitative overall yields which makes this procedure facile and rapid to execute.