3553-94-4

Upstream product

• 105-60-2 caprolactam 
• 75-77-4 chloro-trimethyl-silane 
• 25436-07-1 trimethylsilyl trichloroacetate 

Downstream Products

• 75-77-4 chloro-trimethyl-silane 
• 139885-37-3 N,N-Diethyl-2-(2-oxo-azepan-1-yl)-acetamide 
• 105-60-2 caprolactam 
• 2857-97-8 trimethylsilyl bromide 
• 140-88-5 ethyl acrylate 
• 93969-49-4 3-(6-Methyl-4-oxo-2-phenyl-3,4-dihydro-2H-[1,3]oxazin-2-yl)-azepan-2-one 
• 139885-42-0 (S)-3-Methyl-2-[2-(2-oxo-azepan-1-yl)-acetylamino]-butyric acid methyl ester 
• 124943-51-7 3-(5-Phenyl-pent-4-ynyl)-azepan-2-one 
• 124943-56-2 3-((E)-4-Phenyl-but-3-enyl)-azepan-2-one 
• 124943-55-1 3-(4-Phenyl-but-3-ynyl)-azepan-2-one 
• 139885-40-8 (S)-1-[2-(2-Oxo-azepan-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid ethyl ester 
• 124663-84-9 C₁₅H₂₃NO₄SSi 
• 139885-49-7 1-[2-(4-Isobutyl-5-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-azepan-2-one 
• 79302-54-8 N-(3-trimethylsiloxybenzoyl)-caprolactam 

Relevant academic research and scientific papers

A Fit-for-Purpose Synthesis of (R)-2-Methylazepane

The preparation of new RSV inhibitors required an efficient synthesis of (R)-2-methylazepane ((R)-1) amenable to large-scale production to support preclinical studies. After consideration of different options, an efficient five-step synthesis relying on t

Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO2 and Phenylisocyanate

Lactamomethylsilanes of γ-butyrolactam, δ-valerolactam, ε-caprolactam, and 1-isoindolinone (phthalimidine) with up to three methyl moieties were synthesized according to the chemical formula MexSiLac(4–x) (x = 0, 1, 2, and 3). Using the lactams as starting materials four synthetic routes were tested: salt elimination, transsilylation, transamination, and metallation of the lactames followed by reaction with methylchlorosilanes. All products were analyzed by NMR (1H, 13C and 29Si) and RAMAN spectroscopy. Selected solid products were crystallized and the molecular structure was determined by single-crystal X-ray diffraction. The reactivity of the lactamomethylsilanes towards phenylisocyanate and CO2 was studied.

Ring-Opening Polymerization of Allyl-Functionalized Lactams

Aliphatic polyamides containing pendent allyl groups were prepared by anionic ring-opening copolymerization of -caprolactam with monomer 1, the substituted lactam 3-(3-propenyl)-2-azepanone. Copolymerization experiments revealed that up to 11 mol % of 1 was integrated successfully into these novel polyamides, which ranged in molecular weight from 27 to 72 kDa. Relative to the well-known commercial polyamide-6 (PA-6), the degree of crystallinity of the copolymers decreased with incorporation of functional monomer. Moreover, the pendent allyl groups afforded rapid access to numerous functional aliphatic polyamides, using photoinitiated thiol-ene chemistry, providing a pathway to cross-linked polyamide films and gels.

Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives

A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.

Highly effective asymmetric hydrogenation of cyclic N -alkyl imines with chiral cationic Ru-MsDPEN catalysts

A range of cyclic N-alkyl imines were efficiently hydrogenated by using a chiral cationic Ru(η6-cymene)(MsDPEN)(BArF) complex (MsDPEN = N-(methanesulfonyl)-1,2-diphenylethylenediamine) in high yields and up to 98% ee. A one-pot synthesis of chiral 2-phenylpyrrolidine via reductive amination was also developed.

A double alkylation - Ring closing metathesis approach to spiroimines

As part of a programme directed towards the synthesis of the marine toxins, the spirolides and gymnodimine, a convenient synthesis of the key bicyclic spiroimine ring systems has been developed. The method involves double alkylation of a simple lactam, Grubbs ring closing metathesis of the resultant dialkylated lactam then reduction of the lactam to an imine.

Dual protein farnesyltransferase-geranylgeranyltransferase-I inhibitors as potential cancer chemotherapeutic agents

A series of novel diaryl ether lactams have been identified as very potent dual inhibitors of protein farnesyltransferase (FTase) and protein geranylgeranyltransferase I (GGTase-I), enzymes involved in the prenylation of Ras. The structure of the complex formed between one of these compounds and FTase has been determined by X-ray crystallography. These compounds are the first reported to inhibit the prenylation of the important oncogene Ki-Ras4B in vivo. Unfortunately, doses sufficient to achieve this endpoint were rapidly lethal.

Synthesis of Spirocyclic Imines: Key Pharmacophores in the Shellfish Toxins Spirolides and Gymnodimine

The efficient synthesis of several spirocyclic imines of similar structure to that present in the shellfish toxins, the spirolides and gymnodimine, is described. The key steps involved double α-alkylation of simple lactam starting materials, Grubbs' ring closing metathesis of the resultant bis-alkylated lactams and LiEt3BH reduction of the TEOC protected lactams to imines.

Inhibitors of prenyl-protein transferase

The present invention is directed to compounds which inhibit prenyl-protein transferase and particularly, the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this in

Inhibitors of prenyl-protein transferase

The present invention is directed to azepan-2-one compounds which inhibit prenyl-protein transferase, particularly farnesyl-protein transferase (Ftase), and the prenylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting prenyl-protein transferase and the prenylation of the oncogene protein Ras.