55791-75-8

Upstream product

• 111-83-1 1-bromo-octane 
• 150-13-0 4-amino-benzoic acid 
• 111-86-4 n-Octylamine 
• 104-88-1 4-chlorobenzaldehyde 
• 124-13-0 Octanal 
• 586-76-5 4-Bromobenzoic acid 
• 94-09-7 p-aminoethylbenzoate 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 260412-02-0 4-octylamino-benzoic acid phenyl ester 
• 65536-29-0 2,3-dihydroxypropyl 4-(n-octylamino)benzoate 
• 1012103-31-9 2-(dimethylamino)ethyl 4-(octylamino)benzoate 
• 1312300-89-2 4-(octylamino)-N-(2-(dimethylamino)ethyl)benzamide 
• 1344028-85-8 4-(octylamino)-3-bromobenzoic acid 

Relevant academic research and scientific papers

Stereoselectivity in dehydrative cyclic trimerization of substituted 4-alkylaminobenzoic acids

The cyclic trimerization of substituted 4-alkylaminobenzoic acids was investigated. From NMR analyses of DiMeO_C3A with two methoxy groups, which was obtained by using SiCl4 as a dehydrative condensation reagent and purified by preparative GPC, a syn/anti

DERIVATIVES OF TETRACAINE

Disclosed herein are derivatives of tetracaine that, among other things, block cyclic nucleotide gated (CNG) channels and are useful in the treatment of diseases characterized by overactive CNG channels such as retinal degeneration diseases.

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

Cyclic nucleotide-gated channel block by hydrolysis-resistant tetracaine derivatives

To meet a pressing need for better cyclic nucleotide-gated (CNG) channel antagonists, we have increased the biological stability of tetracaine-based blockers by synthesizing amide and thioamide linkage substitutions of tetracaine (1) and a higher affinity

A highly versatile catalyst system for the cross-coupling of aryl chlorides and Amines

The syntheses of 2-(di-tertbutylphosphino)-N,N-dimethylaniline (L1, 71%) and 2-(di-1-adamantylphosphino)-N,N-dimethylaniline (L2, 74%), and their application in BuchwaldHartwig amination, are reported. In combination with [Pd(allyl)Cl]2 or [Pd(cinnamyl)Cl]2, these structurally simple and air-stable P,N ligands enable the cross-coupling of aryl and heteroaryl chlorides, including those bearing as substituents enolizable ketones, ethers, esters, carboxylic acids, phenols, alcohols, olefins, amides, and halogens, to a diverse range of amine and related substrates that includes primary alkyl- and arylamines, cyclic and acyclic secondary amines, N-H imines, hydrazones, lithium amide, and ammonia. In many cases, the reactions can be performed at low catalyst loadings (0.5-0.02 mol % Pd) with excellent functional group tolerance and chemoselectivity. Examples of cross-coupling reactions involving 1,4-bromochlorobenzene and iodobenzene are also reported. Under similar conditions, inferior catalytic performance was achieved when using Pd(OAc)2, PdCl2, [PdCl2(cod)] (cod = 1,5-cyclooctadiene), [PdCl 2(MeCN)2], or [Pd2(dba)3] (dba = dibenzylideneacetone) in combination with L1 or L2, or by use of [Pd(allyl)Cl]2 or [Pd(cinnamyl)Cl]2 with variants of L1 and L2 bearing less basic or less sterically demanding substituents on phosphorus or lacking an ortto-dimethylamino fragment. Given current limitations associated with established ligand classes with regard to maintaining high activity across the diverse possible range of C-N coupling applications, L1 and L2 represent unusually versatile ligand systems for the cross-coupling of aryl chlorides and amines

Cu-Al hydrotalcite: An efficient and reusable ligand-free catalyst for the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines

Copper-aluminum hydrotalcite catalysts were effectively used in the coupling of aryl chlorides with aliphatic, aromatic, and N(H)-heterocyclic amines to afford the corresponding N-alkylated/arylated amines in excellent yields. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity. Georg Thieme Verlag Stuttgart.

Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: Scope and structure-activity relationships

We describe a systematic study of the scope and relationship between ligand structure and activity for a highly efficient and selective class of catalysts containing sterically hindered chelating alkylphosphines for the amination of heteroaryl and aryl chlorides, bromides, and iodides. In the presence of this catalyst, aryl and heteroaryl chlorides, bromides, and iodides react with many primary amines in high yields with part-per-million quantities of palladium precursor and ligand. Many reactions of primary amines with both heteroaryl and aryl chlorides, bromides, and iodides occur to completion with 0.0005-0.05 mol % catalyst. A comparison of the reactivity of this catalyst for the coupling of primary amines at these loadings is made with catalysts generated from hindered monophosphines and carbenes, and these data illustrate the benefits of chelation. Studies on structural variants of the most active catalyst indicate that a rigid backbone in the bidentate structure, strong electron donation, and severe hindrance all contribute to its high reactivity. Thus, these complexes constitute a fourth-generation catalyst for the amination of aryl halides, whose activity complements catalysts based on monophosphines and carbenes.

Block of cyclic nucleotide-gated channels by tetracaine derivatives: Role of apolar interactions at two distinct locations

A series of new tetracaine derivatives was synthesized to explore the effects of hydrophobic character on blockade of cyclic nucleotide-gated (CNG) channels. Increasing the hydrophobicity at either of two positions on the tetracaine scaffold, the tertiary amine or the butyl tail, yields blockers with increased potency. However, shape also plays an important role. While gradual increases in length of the butyl tail lead to increased potency, substitution of the butyl tail with branched alkyl or cyclic groups is deleterious.

[(CyPF-Bu)PdCI2]: An air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides

(Chemical Equation Presented) An air- and moisture-stable palladium catalyst, [(CyPF-1Bu)PdCI2] (1), for coupling of heteroaryl chlorides, bromides, and iodides with a variety of primary amines is described. Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups.

Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles

Resisting pathways for decomposition followed by palladium complexes of monodentate ligands is one characteristic of the highly reactive but long-lived catalyst generated from the Josiphos ligand L and palladium. It catalyzes under mild conditions the coupling of primary amines with chloropyridines and chloroarenes in high yield with low catalyst loadings (see scheme).