78385-36-1

Usage

Uses

Used in Organic Synthesis:
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is used as a reactant for the atypical aza-Morita-Baylis-Hillman mechanism, which is a carbonyl addition reaction involving imines and aldehydes. This reaction allows for the formation of nitrogen-containing compounds with potential applications in the synthesis of pharmaceuticals and other organic molecules.
Used in Thermal Decomposition:
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is also used in thermal decomposition processes, where it can be heated to release the benzyloxycarbonylmethyl group as a leaving group. This process can be employed in the synthesis of various organic compounds, including those with potential applications in the pharmaceutical industry.
Used in Double Aza-Michael Reaction:
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is utilized in double aza-Michael reactions, which involve the addition of two nitrogen-containing nucleophiles to a Michael acceptor. This reaction can lead to the formation of complex nitrogen-containing compounds with potential applications in various industries, including pharmaceuticals and materials science.
Used in Cyclodextrin Derivatives:
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is used as a reactant in the synthesis of cyclodextrin derivatives, which are cyclic oligosaccharides known for their ability to form inclusion complexes with various guest molecules. Cyclodextrin derivatives have applications in drug delivery, food science, and other industries due to their unique properties.
Used in Stereoselective Preparation of α,β-Unsaturated Carbonyl Compounds:
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is used in the stereoselective preparation of α,β-unsaturated carbonyl compounds via stereoselective Wittig olefination with aldehydes. This process can be carried out under solventless conditions or using ultrasonication, which can improve the efficiency and selectivity of the reaction. The resulting α,β-unsaturated carbonyl compounds have potential applications in the synthesis of various organic molecules and pharmaceuticals.
Used in Synthesis of [Difluoro(alkenylphenyl)methyl]phosphonic Acids:
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is used in the synthesis of [difluoro(alkenylphenyl)methyl]phosphonic acids on non-crosslinked polystyrene as inhibitors of PTP-1B via Wittig reaction. PTP-1B is a protein tyrosine phosphatase that plays a role in various cellular processes, and its inhibition can have therapeutic applications in the treatment of various diseases, including diabetes and cancer.

InChI:InChI=1/C27H24O2P.BrH/c28-27(29-21-23-13-5-1-6-14-23)22-30(24-15-7-2-8-16-24,25-17-9-3-10-18-25)26-19-11-4-12-20-26;/h1-20H,21-22H2;1H/q+1;/p-1

Upstream product

• 100-51-6 benzyl alcohol 
• 5437-45-6 Benzyl bromoacetate 
• 603-35-0 triphenylphosphine 

Downstream Products

• 307494-00-4 (E)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-2-enoic acid benzyl ester 
• 15097-38-8 (carbobenzyloxymethylene)triphenylphosphorane 
• 187661-86-5 buta-2,3-dienoic acid benzyl ester 
• 481014-56-6 (±)-benzyl penta-2,3-dienoate 
• 139132-06-2 benzyl 2-cyclopropylideneacetate 
• 445396-69-0 (2E,6E)-(4R,5R)-4,5-Bis-benzyloxy-heptadeca-2,6-dienoic acid benzyl ester 
• 445396-70-3 (2E,6E)-(4R,5R)-4,5-Bis-benzyloxy-7-phenyl-hepta-2,6-dienoic acid benzyl ester 
• 445396-68-9 (2E,6E)-(4R,5R)-4,5-Bis-benzyloxy-deca-2,6-dienoic acid benzyl ester 
• 445396-67-8 (2E,6E)-(4R,5R)-4,5-Bis-benzyloxy-nona-2,6-dienoic acid benzyl ester 
• 445396-58-7 (E)-(4R,5R)-4,5-Bis-benzyloxy-hex-2-enoic acid benzyl ester 
• 146737-68-0 benzyl 4-(indan-2-yl)-2-butenoate 
• 116998-17-5 4,4,4-Trifluoro-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid benzyl ester 
• 78385-35-0 benzyloxycarbonylbromomethylenetriphenylphosphorane 

Relevant academic research and scientific papers

Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E -selectivity.

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

DMAP Mediated Efficient Construction of Functionalized Chromenes through One-Pot Reaction of para-Quinone Methides with Allenoates

A novel DMAP-mediated Rauhut-Currier/oxa-Michael addition cascade reaction of hydroxylphenyl-substituted para-quinone methide with allenoate was reported for the first time. A series of functionalized chromenes were successfully obtained with moderate to

Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones

An efficient enantioselective [3+2] cycloaddition of isomünchnones with methyleneindolinones that are generated by anin situintramolecular addition of the carbonyl group to rhodium carbenes is realized with a chiralN,N′-dioxide/Zn(ii) complex as a Lewis acid. A series of chiral oxa-bridged 3-spiropiperidines are obtained in high yields with excellent dr and excellent ee values.

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.

SUBSTITUTED PYRROLIDINES AND THEIR USE

The invention discloses compounds of Formula (I) wherein R1, R2, R3, R3A, R4, and R5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.

NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates

An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.