1075-28-1

Upstream product

• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 95-46-5 2-methylphenyl bromide 
• 15115-58-9 3-(2-bromophenyl)propionic acid 
• 42918-20-7 1-allyl-2-bromobenzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 

Downstream Products

• 52221-90-6 [3-(2-Bromo-phenyl)-propyl]-phosphonic acid diethyl ester 
• 169626-57-7 5,5-bis(ethoxycarbonyl)-8-(2'-bromophenyl)-1,2-octadiene 
• 74685-38-4 C₃₁H₆₀O₃Si 
• 685087-65-4 1-benzyl-1-phenyl-1-sila-1,2,3,4-tetrahydronaphthalene 
• 685087-79-0 (SiRS)-1-(1R,2S,5R)-menthoxy-1-naphthyl-1-sila-1,2,3,4-tetrahydronaphthalene 
• 924661-31-4 (SiS)-1-isopropyl-1-[(1R,2S,5R)-1-menthyloxy]-1,2,3,4-tetrahydro-1-silanaphthalene 

Relevant academic research and scientific papers

Iridium-Catalyzed Cycloisomerization of Alkynoic Acids: Synthesis of Unsaturated Lactones

The iridium-catalyzed cycloisomerization of various alkynoic acids was successfully developed, and a series of five-, six-, and especially seven-membered unsaturated lactones were constructed with moderate yields and excellent regioselectivities (up to 68

Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp3)-H Bond Functionalization

Herein we report a diastereoselective synthesis of medium-sized carbocycle-fused piperidines via [1,n (n = 6, 7)]-[1,5]-sequential hydride shift triggered double C(sp3)-H bond functionalization. When cinnamylidene malonates having N,N-dibenzyl propylamine moiety were treated with 5 mol % of Yb(OTf)3, a [1,6]-[1,5]-sequential hydride shift/cyclization process proceeded to afford seven-membered carbocycle-fused piperidines with excellent diastereoselectivities. This sequential system was applicable to the synthesis of eight-membered carbocycle-fused piperidines by an unprecedented [1,7]-[1,5]-sequential hydride shift/cyclization process.

Expedient Access to 2-Benzazepines by Palladium-Catalyzed C?H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold

Bioactive 2-benzazepines were accessed in an atom- and step-economical manner through a versatile palladium-catalyzed C?H activation strategy. The C?H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional-group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable potential for anti-cancer applications.

MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R1, R2, R3, W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

Modulators of Cystic Fibrosis Transmembrane Conductance Regulator

The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R1, R2, R3, W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

Structural effects in radical clocks and mechanisms of grignard reagent formation: Special effect of a phenyl substituent in a radical clock when the crossroads of selectivity is at a metal/solution interface

A large class of radical clocks is based on the intramolecular trapping of a reactive radical by a suitably located, unsaturated system. Depending on the substituents present on this unsaturated system, the rate of cyclisation may vary drastically. This property has been repeatedly used, to diagnose the participation of very short-lived radicals in the mechanisms of a wide variety of reactions. For reactions occurring in homogeneous solution, a phenyl substituent capable of stabilizing the radical formed during the act of trapping has been one of the most widely used tools of this type. During study of the mechanisms of formation of Grignard reagents - reactions that occur at the interface of the metal and the solution - the phenyl substituent displayed a specific new behaviour pattern. Besides its stabilizing role, it was also able to play the role of mediator in redox catalysis of electron transfer. In this case, the first events on the pathway to the Grignard reagents involve a cascade of three (one intermolecular followed by two intramolecular) electron transfers. Introduction of a p-methoxy substituent on the phenyl ring, making the phenyl group a poorer electron acceptor, suppresses this specific second role. Applied to the mechanism of Grignard reagent formation, this p-methoxy effect is consistent with a triggering mechanistic act of electron transfer from the metal to the aryl halide rather than with a concerted oxidative addition. A similar change in selectivity is observed, when a p-methoxy group is introduced onto a phenyl group that also bears a halogen, but its origin is different: this effect is associated with the shortening of the lifetime of the radical anion formed by the triggering electron transfer. These observations reemphasise our earlier proposals to use concepts originating from, electrochemical kinetics to explain, the selectivities of reactions occurring at metal/solution interfaces. This conjecture could possibly hold for any interface where the diffusion of reactive species plays a role in the settling of selectivity. These concepts emphasise the necessity to consider, for each reactive species, their average distance of diffusion away from the metal/solution interface. Wiley-VCH Verlag GmbH & Co. KGaA.

Indium-catalyzed cycloisomerization of ω-alkynyl-β-ketoesters into six- to fifteen-membered rings

(Chemical Equation Presented) Many different sizes of rings available: Heating ω-alkynyl-β-ketoesters in the presence of In(NTf 2)3 (Tf=trifluoromethanesulfonyl) produces six- to fifteen-membered ring products in good yields. The reaction features low catalyst loading and moderately dilute conditions, and the formation of medium-sized rings is sometimes faster than that for the corresponding six-membered rings. A synthesis of (±)-muscone is also reported.

A Convergent Method for the Synthesis of Highly Enantiomerically Enriched Cyclic Silanes with Silicon-Centered Chirality

A preparatively straightforward methodology has been developed which allows the assembly of silicon-containing carbocycles as mixtures of diastereomers with silicon as the sole center of stereogenic information. One-step construction of the chiral cyclic silanes is realized by reaction of equimolar amounts of a dibromide and a chirally modified dichlorosilane under Barbier conditions giving access to several monofunctionalized 1-sila-1,2,3,4-tetrahydronaphthalenes and a corresponding phenanthrene derivative. Facile large scale syntheses of 3-(2-bromoaryl)propyl bromides as well as dichlorosilanes have been elaborated. This highly convergent methodology relies on the novel (-)-menthyloxy-substituted dichlorosilanes, which have the chiral auxiliary for the subsequent optical resolution installed. These enantiopure dichlorosilanes are useful building blocks for a general and modular one-step approach to silanes with silicon-centered chirality since this strategy avoids the linear sequences reported in literature. The optical resolution has been exemplarily optimized for the 1-phenyl-1-sila-1,2,3,4- tetrahydronaphthalene derivative and the absolute configuration has been established by X-ray crystallography. The chiral auxiliary is stereospecifically displaced by simple reduction providing the highly enantioenriched silane (er = 98:2) which is enantiospecifically chlorinated as verified by a Walden inversion at silicon.