Day: January 4, 2023

Tertiary Alcohols as Radical Precursors for the Introduction of Tertiary Substituents into Heteroarenes was written by Pitre, Spencer P.;Muuronen, Mikko;Fishman, Dmitry A.;Overman, Larry E.. And the article was included in ACS Catalysis in 2019.Recommanded Product: 1-Boc-4-Hydroxy-4-methylpiperidine This article mentions the following:

Despite many recent advances in the radical alkylation of electron-deficient heteroarenes since the seminal reports by Minisci and co-workers, methods for the direct incorporation of tertiary alkyl substituents into nitrogen heteroarenes are limited. This report describes the use of tert-alkyl oxalate salts, derived from tertiary alcs., to introduce tertiary substituents into a variety of heterocyclic substrates. This reaction has reasonably broad scope, proceeds rapidly under mild conditions, and is initiated by either photochem. or thermal activation. Insights into the underlying mechanism of the higher yielding visible-light initiated process were obtained by flash photolysis studies, whereas computational studies provided insight into the reaction scope. In the experiment, the researchers used many compounds, for example, 1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1Recommanded Product: 1-Boc-4-Hydroxy-4-methylpiperidine).

1-Boc-4-Hydroxy-4-methylpiperidine (cas: 406235-30-1) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst. Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.Recommanded Product: 1-Boc-4-Hydroxy-4-methylpiperidine

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Discovery of BRD4 bromodomain inhibitors by fragment-based high-throughput docking was written by Zhao, Hongtao;Gartenmann, Lisa;Dong, Jing;Spiliotopoulos, Dimitrios;Caflisch, Amedeo. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2014.Quality Control of 1-Tosylpiperidin-4-one This article mentions the following:

Bromodomains (BRDs) recognize acetyl-lysine modified histone tails mediating epigenetic processes. BRD4, a protein containing two bromodomains, has emerged as an attractive therapeutic target for several types of cancer as well as inflammatory diseases. Using a fragment-based in silico screening approach, we identified two small mols. that bind to the first bromodomain of BRD4 with low-micromolar affinity and favorable ligand efficiency (0.37 kcal/mol per non-hydrogen atom), selectively over other families of bromodomains. Notably, the hit rate of the fragment-based in silico approach is about 10% as only 24 putative inhibitors, from an initial library of about 9 million mols., were tested in vitro. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Quality Control of 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine ring can be found not only in more than half of the currently known structures of alkaloids, but also in many natural or synthetic compounds with interesting biological activities. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.Quality Control of 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Cyano phosphate: an efficient intermediate for the chemoselective conversion of carbonyl compounds to nitriles was written by Yoneda, Ryuji;Harusawa, Shinya;Kurihara, Takushi. And the article was included in Journal of Organic Chemistry in 1991.SDS of cas: 33439-27-9 This article mentions the following:

Cyanohydrin di-Et phosphates, readily obtained from various ketones and aldehydes by reaction with di-Et phosphorocyanidate and lithium cyanide, reacted chemoselectively with SmI₂ in THF to give the corresponding nitriles in excellent yields. This method was also found applicable to α,β-unsaturated carbonyl compounds via cyano phosphates to give β,γ-unsaturated nitriles, not obtainable by standard methods, without isomerization of the double bonds. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9SDS of cas: 33439-27-9).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine and its derivatives have become increasingly popular in many synthetic schemes. Some chemotherapeutic agents have piperidine moiety within their structure, foremost among them, vinblastine and raloxifene.SDS of cas: 33439-27-9

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of pyrido[3,4-b]pyrano[3,4-b]indoles was written by Freter, Kurt;Fuchs, Victor. And the article was included in Journal of Heterocyclic Chemistry in 1982.Synthetic Route of C12H15NO3S This article mentions the following:

Pyridopyranoindoles I (R = H, Me; R¹ = Ph, Me; R² = H, Me, Ac, tosyl, COCH₂NEt₂, CH₂CH₂NEt₂, CH₂Ph, CH₂CH₂Ph, (CH₂)₃Ph, CH₂CH₂OPh; R³ = H, OMe) were prepared by treating the indolylpiperidinols II with Me₂CO or PhCHO. Some I have antihypertensive activity. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine has a role as a reagent, a protic solvent, a base, a catalyst, a plant metabolite, a human metabolite and a non-polar solvent. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Structure-Based Optimization of Thiophene[3,2-d]pyrimidine Derivatives as Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors with Improved Potency against Resistance-Associated Variants was written by Kang, Dongwei;Fang, Zengjun;Huang, Boshi;Lu, Xueyi;Zhang, Heng;Xu, Haoran;Huo, Zhipeng;Zhou, Zhongxia;Yu, Zhao;Meng, Qing;Wu, Gaochan;Ding, Xiao;Tian, Ye;Daelemans, Dirk;De Clercq, Erik;Pannecouque, Christophe;Zhan, Peng;Liu, Xinyong. And the article was included in Journal of Medicinal Chemistry in 2017.Name: tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate This article mentions the following:

This work follows on from our initial discovery of a series of piperidine-substituted thiophene[3,2-d]pyrimidine HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTI) (J. Med. Chem. 2016, 59, 7991-8007). In the present study, we designed, synthesized, and biol. tested several series of new derivatives in order to investigate previously unexplored chem. space. Some of the synthesized compounds displayed single-digit nanomolar anti-HIV potencies against wild-type (WT) virus and a panel of NNRTI-resistant mutant viruses in MT-4 cells. I was exceptionally potent against the whole viral panel, affording 3-4-fold enhancement of in vitro antiviral potency against WT, L100I, K103N, Y181C, Y188L, E138K, and K103N+Y181C and 10-fold enhancement against F227L+V106A relative to the reference drug etravirine (ETV) in the same cellular assay. The structure-activity relationships, pharmacokinetics, acute toxicity, and cardiotoxicity were also examined Overall, the results indicate that I is a promising new drug candidate for treatment of HIV-1 infection. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate (cas: 934536-10-4Name: tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate).

tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate (cas: 934536-10-4) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Name: tert-Butyl 4-amino-3-fluoropiperidine-1-carboxylate

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Methyl Radical Initiated Kharasch and Related Reactions was written by Tappin, Nicholas D. C.;Renaud, Philippe. And the article was included in Advanced Synthesis & Catalysis in 2021.Synthetic Route of C12H15NO3S This article mentions the following:

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive Me radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N₂) or volatile (acetone and Me halide) thereby facilitating greatly product purification by either flash column chromatog. or distillation In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 min under normal atm.) and a low excess of the radical precursor reagent (2 equiv) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-Bu peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous byproducts (CO₂). In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a metabolite of cadaverine, a polyamine found in the human intestine. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Catalytic Asymmetric α-Alkylation of Ketones and Aldehydes with N-Benzylic Sulfonamides through Carbon-Nitrogen Bond Cleavage was written by Weng, Zhen-Tao;Li, Yuan;Tian, Shi-Kai. And the article was included in Journal of Organic Chemistry in 2011.Formula: C12H15NO3S This article mentions the following:

A range of ketones and aldehydes smoothly undergoes asym. S_N1 α-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent yields and with good enantioselectivity. This chem. has been successfully extended to the asym. desymmetrization of 4-substituted cyclohexanones, which exhibits greater than 99:1 diastereoselectivity and good enantioselectivity. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Formula: C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. Piperidine prefers a chair conformation, similar to cyclohexane. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an axial position, and the other in an equatorial position.Formula: C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Synthesis of Functionalized Medium-Sized trans-Cycloalkenes by 4π Electrocyclic Ring Opening/Alkylation Sequence was written by Ito, Tomohiro;Tsutsumi, Masaki;Yamada, Ken-ichi;Takikawa, Hiroshi;Yamaoka, Yousuke;Takasu, Kiyosei. And the article was included in Angewandte Chemie, International Edition in 2019.Synthetic Route of C12H15NO3S This article mentions the following:

Development of a novel synthetic method for medium-sized trans-cycloalkenes (TCAs), e.g., I is described. Functionalized TCAs e.g., I are readily prepared from simple cycloalkanone such as tert-butyl(cyclohept-1-en-1-yloxy)dimethylsilane, in a few steps, namely, enol silyl ether formation, [2+2] cycloaddition, and domino 4π electrocyclic ring opening/alkylation (conjugate addition). The first example of central-to-planar chirality transfer from enantiomerically enriched cyclobutenes, e.g., II to TCAs e.g., I is also described. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Synthetic Route of C12H15NO3S).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine moiety constitutes an important building block for the synthesis of a variety of bioactive natural products, alkaloids and other drugs. Piperidine derivatives bearing a masked aldehyde function in the ε-position are easily transformed into quinolizidine compounds through intramolecular reductive amination.Synthetic Route of C12H15NO3S

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Copper-Catalyzed One-Pot Borylative Aldolisation β-Fluoride Elimination for the Formal Addition of Acrylates to Carbonyl Moieties was written by Rasson, Corentin;Stouse, Adrien;Boreux, Arnaud;Cirriez, Virginie;Riant, Olivier. And the article was included in Chemistry – A European Journal in 2018.Recommanded Product: 1-Tosylpiperidin-4-one This article mentions the following:

Herein, we report the copper-catalyzed domino borylation/aldolisation of Me 2-fluoroacrylate with carbonyl compounds followed by an elimination to give Morita-Baylis-Hillman (MBH) analogs. The optimal conditions described were shown to be compatible with a wide range of aldehydes and ketones. Unprecedented MBH adducts derived from ketones were efficiently synthesized. In the experiment, the researchers used many compounds, for example, 1-Tosylpiperidin-4-one (cas: 33439-27-9Recommanded Product: 1-Tosylpiperidin-4-one).

1-Tosylpiperidin-4-one (cas: 33439-27-9) belongs to piperidine derivatives. The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. Several piperidine alkaloids isolated from natural herbs, were found to exhibit antiproliferation and antimetastatic effects on various types of cancers both in vitro and in vivo for example Piperine, Evodiamine, Matrine, Berberine and Tetrandine.Recommanded Product: 1-Tosylpiperidin-4-one

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liquid-crystalline side chain polysiloxanes with 4-amino-4′-stilbenecarboxylic ester mesogens was written by Bautista, Marietta O.;Duran, Randolph S.;Ford, Warren T.. And the article was included in Macromolecules in 1993.HPLC of Formula: 4045-22-1 This article mentions the following:

Side chain polysiloxanes with 4-(dimethylamino)- and 4-[4-(hexyloxy)piperidino]-4′-stilbenecarboxylic ester mesogens were synthesized from poly(hydromethylsiloxane) and poly(hydromethylsiloxane-co-dimethylsiloxane) and the 10-undecen-1-yl esters. Size-exclusion chromatog. (SEC) underestimated M_n of the (dimethylamino)stilbene homopolymer by a factor of 4 and M_n of the piperidinostilbene homopolymer by a factor of 2 compared with ¹H NMR end group analyses. SEC and NMR values of M_n approx. agreed for the copolymers. The phases of the monomers and polysiloxanes were assigned by polarizing microscopy and x-ray diffraction. The copolysiloxanes had T_g near -40° by DSC, but T_g was not detected for the homopolysiloxanes. Both homopolysiloxanes have nematic phases, and both copolymers have S_A phases. The [(hexyloxy)piperidino]silbene polymers have more ordered phases, assigned as S_B of the copolymer and either S_B or hexagonal nematic of the homopolymer. The isotropic transitions were detected by polarizing microscopy but not by DSC. All of the polysiloxanes form stable monolayers on water that can be compressed to mean areas per stilbene repeat unit ranging from 23 to 34 Ų and to pressure of â‰?0 mN/m. In the experiment, the researchers used many compounds, for example, 1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1HPLC of Formula: 4045-22-1).

1-(4-Hydroxypiperidin-1-yl)ethanone (cas: 4045-22-1) belongs to piperidine derivatives. Piperidine is a saturated organic heteromonocyclic parent, an azacycloalkane, a secondary amine and a member of piperidines. The piperidine and polyhydroxylated indolizidine derivatives have shown to be promising α-glucosidase inhibitors. The former are analogs of DNJ with an improved α-glucosidase inhibitory profile than that of DNJ. Boisson et al.HPLC of Formula: 4045-22-1

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem