3553-93-3

Usage

Uses

Used in Organic Synthesis:
1-(Trimethylsilyl)piperidine-2-one is used as a synthetic building block for the creation of various organic compounds. Its unique structure, which includes a trimethylsilyl group and a piperidine-2-one moiety, allows it to be a versatile intermediate in the synthesis of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(Trimethylsilyl)piperidine-2-one is used as a key intermediate in the development of new drugs. Its ability to be modified and incorporated into complex molecular structures makes it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 1-(Trimethylsilyl)piperidine-2-one is utilized as a starting material for the synthesis of new pesticides, herbicides, and other crop protection agents. Its unique properties enable the development of more effective and targeted products for agricultural use.
Used in Specialty Chemicals:
1-(Trimethylsilyl)piperidine-2-one also finds application in the specialty chemicals market, where it is used to create compounds with specific properties for various industrial applications, such as materials science, coatings, and adhesives. Its versatility and reactivity make it a valuable component in the development of innovative products.

Upstream product

• 675-20-7 piperidin-2-one 
• 75-77-4 chloro-trimethyl-silane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 75-77-4 chloro-trimethyl-silane 
• 85841-56-1 1-<(bromomethyl)dimethylsilyl>-2-piperidone 
• 85841-57-2 1-<(bromodimethylsilyl)methyl>-2-piperidone 
• 93969-50-7 6-Methyl-2-(2-oxo-piperidin-3-yl)-2-phenyl-2,3-dihydro-[1,3]oxazin-4-one 
• 85841-55-0 1-<(chloromethyl)dimethylsilyl>-2-piperidone 
• 76128-62-6 1-(Dimethylchlorosilylmethyl)-2-piperidone 
• 400-53-3 trimethylsilyl trifluoroacetate 
• 124943-49-3 3-(5-Phenyl-pent-4-ynyl)-piperidin-2-one 
• 139885-39-5 (S)-1-[2-(2-Oxo-piperidin-1-yl)-acetyl]-pyrrolidine-2-carboxylic acid ethyl ester 
• 124663-83-8 C₁₄H₂₁NO₄SSi 
• 139885-48-6 1-[2-(4-Isobutyl-5-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-piperidin-2-one 
• 139974-07-5 1-[2-((R)-4-Isobutyl-5-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-piperidin-2-one 
• 19365-08-3 3-hydroxypiperidin-2-one 
• 675-20-7 piperidin-2-one 

Relevant academic research and scientific papers

Structure-activity relationships of benzylidene anabaseines in nicotinic acetylcholine receptors of cockroach nerve cords

Ten analogues of 6′-chloro-3-benzylideneanabaseine (CBA) bearing substituents at the ortho- and the para-positions of the phenyl group were synthesized, together with two related compounds. The affinity of the synthesized compounds for nicotinic acetylcholine receptors (nAChRs) in the nerve cord of the American cockroach (Periplaneta americana L.) was examined by the radioligand binding assay using [3H]epibatidine (EPI), a nAChR agonist. All 12 tested compounds inhibited [3H]EPI binding, showing Ki values ranging from 14.6 to 6830 nM. The potency variation of para-substituted CBA analogues was explained by the steric (ΔB1) and electronic (σp) parameters of the para-substituents, or by the steric parameter and the charge of the N1 nitrogen atom (qN1). Among the CBA analogues, only two compounds containing a dimethylamino group and a methoxy group at the para-position showed high insecticidal activity against the German cockroach (Blattella germanica) when injected after pretreatment with metabolic inhibitors. High-affinity analogues of CBA might be suitable probes for use in classifying and characterizing insect nAChR subtypes.

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.

Novel Ligustrazine-Based Analogs of Piperlongumine Potently Suppress Proliferation and Metastasis of Colorectal Cancer Cells in Vitro and in Vivo

Piperlongumine 1 increases reactive oxygen species (ROS) levels and preferably induces cancer cell apoptosis by triggering different pathways. However, the poor solubility of 1 limits its intensive investigation and clinical application. Ligustrazine possesses a water-soluble pyrazine skeleton and can inhibit proliferation and metastasis of cancer cells. We synthesized compound 3 by replacement of the trimethoxyphenyl of 1 with ligustrazine moiety and further introduced 2-Cl, -Br, and -I to 3 for synthesis of 4-6, respectively. Compound 4 possessed 14-fold greater aqueous solubility than 1 and increased ROS levels in colorectal cancer HCT-116 cells. Additionally, 4 preferably inhibited proliferation, migration, invasion, and heteroadhesion of HCT-116 cells. Treatment with 4 suppressed tumor growth and lung metastasis in vivo and prolonged the survival of tumor-bearing mice. Furthermore, 4 mitigated TGF-β1-induced epithelial-mesenchymal transition and Wnt/β-catenin activation by inhibiting the Akt and GSK-3β phosphorylation in HCT-116 cells. Collectively, 4 displayed significant antiproliferation and antimetastasis activities, superior to 1.

Synthesis and evaluation of N-heteroaromatic ring-based analogs of piperlongumine as potent anticancer agents

Piperlongumine (PL) selectively targets a wide spectrum of cancer cells and induces their death by triggering various pathways, including apoptosis, necrosis and autophagy. However, the poor solubility is a serious concern for intensive study and clinical application. We synthesized its analogs 1–9 by replacement of the trimethoxyphenyl of PL with an N-heteroaromatic ring and/or not introduction of 2-Cl. These compounds improved aqueous solubility and displayed potent anticancer activity. The most active compound 9 selectively enhanced ROS levels in colon cancer cells and inhibited the cell proliferation but sparing non-tumor colon cells. Importantly, 9 significantly repressed tumor growth in an HCT-116 xenograft mouse model, suggesting that these N-heteroaromatic ring-based analogs of PL warrant further investigation.

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.

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.

Studies toward gymnodimine: development of a single-pot Hua reaction for the synthesis of highly hindered cyclic imines.

[structure: see text]. In studies directed toward gymnodimine and related marine toxins, a single-pot variation of the Hua cyclic imine synthesis has been developed. The reaction involves generation of N-trimethylsilyl lactams in situ followed by alkyllithium addition leading directly to cyclic imines. Importantly, this reaction proceeds efficiently with highly hindered alpha,alpha-dialkyl lactams, provided 1,2-dimethoxyethane (DME) is used as solvent, leading to stable cyclic imines. Overall, this transformation allows a one-pot coupling of an alkyliodide and a lactam to give a cyclic imine.

Diels-Alder Reaction of the N-Protected 3-Phenylthio-2(1H)-dihydropyridinone Derivatives

Efficient methods for the preparation of N-protected 3-phenylthio-2(1H)-dihydropyridinones from 2-piperidone and their Diels-Alder reaction with 2-trimethylsilyloxybutadiene are described.The role of the electron-withdrawing N-protecting group in the dienophiles is rationalized in terms of the lowered energy level in LUMO.