17125-07-4

Usage

Type of compound

Secondary amine

Structure

Hexene chain with a phenyl group attached to the fifth carbon and an amine group attached to the third carbon

Potential applications

Organic synthesis and medicinal chemistry for the development of pharmaceuticals and bioactive molecules

Hazardous properties

May have hazardous properties if not properly handled

Caution

Handle and use with care

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 356762-89-5 N-(1,1-diphenyl-3-butenyl)amine 
• 27126-20-1 (3-azidopropyl)benzene 

Relevant academic research and scientific papers

Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines

We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.

Sulfonium ion-promoted traceless Schmidt reaction of alkyl azides

Schmidt reaction by sulfonium ions is described. General primary, secondary, and tertiary alkyl azides were converted to the corresponding carbonyl or imine compounds without any trace of the activators. This bond scission reaction through 1,2-migration of C-H and C-C bonds was accessible to the one-pot substitution reaction.

NOVEL HISTONE METHYLTRANSFERASE INHIBITORS

The present invention relates to novel compounds of formula (I) as defined herein. The compounds are inhibitors of histone methyltransferases of the seven-beta-strand family, in particular of KMT9.

Pd(II)-catalyzed allylic C-H amination for the preparation of 1,2- and 1,3-cyclic ureas

A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)2/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.

METHODS OF PREPARING SECONDARY CARBINAMINE COMPOUNDS WITH BORONIC ACIDS

The present application relates to novel methods for the preparation of secondary carbinamine compounds, particularly the preparation of secondary carbinamine compounds of the formula Ia, formula Ib or formula IV from aldehydes of the formula II and boronic acids of the formula III or formula V, in the presence of ammonia or an ammonia equivalent of the formula NH4+X-.

METHODS OF PREPARING PRIMARY, SECONDARY AND TERTIARY CARBINAMINE COMPOUNDS IN THE PRESENCE OF AMMONIA

The present application relates to novel methods for the preparation of primary, secondary and tertiary carbinamine compounds, particularly the preparation of compounds of formulae I, IV and VI, from a carbonyl compound of formula II in the presence of ammonia or an ammonium equivalent of the formula NH4+X-, by way of allylation, crotylation, arylation, reductive amination and catalytic hydrogenation.

α-aminoallylation of aldehydes in aqueous ammonia

α-Aminoallylation of aldehydes in aqueous ammonia has been developed; commercial aqueous ammonia was successfully used, and this method does not require anhydrous conditions thus leading to easy and practical operations.

α-aminoallylation of aldehydes with ammonia: Stereoselective synthesis of homoallylic primary amines

Three-component reactions of aldehydes, ammonia, and allylboronates were found to provide homoallylic primary amines in high yields with high chemo- and stereoselectivities. A two-step, one-pot, stereoselective synthesis of an uncommon α-amino acid, alloisoleucine, was achieved utilizing this reaction. Copyright