13070-01-4

Basic information

• Product Name: piperidine-2-thione
• Synonyms: piperidine-2-thione;2-Piperidinethione;2-Thiopiperidone;Nsc343088
• CAS NO: 13070-01-4
• Molecular Formula: C₅H₉NS
• Molecular Weight: 115.2
• Mol File: 13070-01-4.mol

Chemical Properties

• Boiling Point: 169.068 °C at 760 mmHg
• Flash Point: 56.051 °C
• Appearance: /
• Density: 1.093 g/cm³
• Vapor Pressure: 1.57mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: piperidine-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: piperidine-2-thione(13070-01-4)
• EPA Substance Registry System: piperidine-2-thione(13070-01-4)

Safety Data

• Hazardous Substances Data: 13070-01-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H9NS/c7-5-3-1-2-4-6-5/h1-4H2,(H,6,7)

Upstream product

• 675-20-7 piperidin-2-one 
• 507-09-5 thioacetic acid 
• 133218-34-5 N-(3-Phenylbutyryl)piperidine-2-thione 
• 142-08-5 2-hydroxypyridin 
• 19300-54-0 toluene-4-sulfonic acid pent-4-enyl ester 
• 821-09-0 n-Pent-4-enyl alcohol 
• 821-62-5 5-azidopent-1-ene 
• 100-53-8 phenylmethanethiol 

Downstream Products

• 19766-29-1 6-methylsulfanyl-2,3,4,5-tetrahydro-pyridine 
• 4226-78-2 6-benzylmercapto-2,3,4,5-tetrahydro-pyridine 
• 675-20-7 piperidin-2-one 
• 22780-54-7 2-iminopiperidine 
• 4515-19-9 piperidin-2-one oxime 
• 34845-35-7 2,3-diphenyl-2,3,7,8-tetrahydro-6H-pyrido[2,1-b][1,3]thiazin-4-one 
• 6079-40-9 1,3-bis-(2,3-diphenyl-6,7-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl)-trimethinium; perchlorate 
• 99101-05-0 2,3-diphenyl-5,6,7,8-tetrahydro-thiazolo[3,2-a]pyridinylium; iodide 
• 125880-13-9 1-(2',2'-Dimethyl-3'-butenoyl)piperidine-2-thione 
• 882-33-7 diphenyldisulfane 
• 133218-34-5 N-(3-Phenylbutyryl)piperidine-2-thione 
• 103184-66-3 2-Thioxo-piperidine-3-carbothioic acid phenylamide 
• 103184-67-4 2-Thioxo-piperidine-3-carbothioic acid (4-chloro-phenyl)-amide 
• 121003-23-4 N-acetylpiperidine-2-thione 

Relevant articles and documents

Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy

The AgI-promoted reaction of thiolactams with N-Boc amino acids yields an N-(α-aminoacyl) lactam that can rearrange through an acyl transfer process. Boc-deprotection results in convergence to the ring-expanded adduct, thereby facilitating an overall insertion of an amino acid into the thioamide bond to generate medium-sized heterocycles. Application to the site-specific insertion of amino acids into cyclic peptides is demonstrated.

Evaluation of thioamides, thiolactams and thioureas as hydrogen sulfide (H2S)donors for lowering blood pressure

Hydrogen sulfide (H2S)is a biologically important gaseous molecule that exhibits promising protective effects against a variety of pathological processes. For example, it was recognized as a blood pressure lowering agent. Aligned with the need for easily modifiable platforms for the H2S supply, we report here the preparation and the H2S release kinetics from a series of structurally diversified thioamides, thiolactams and thioureas. Three different thionation methods based on the usage of a phosphorus pentasulfide and Lawesson reagent were applied to prepare the target thioamides and thiolactams. Furthermore, obtained H2S donors were evaluated both in in vivo and in vitro studies. The kinetic parameters of the liberating H2S was determined and compared with NaHS and GYY4137 using two different detection technics i.e.; fluorescence labeling 7-azido-4-methyl-2H-chromen-2-one and 5,5‘-dithiobis (2-nitrobenzoic acid), sulfhydryl probe, also known as the Ellman's reagent. We have proved that the amount of releasing H2S from these compounds is controllable through structural modifications. Finally, the present study shows a hypotensive response to an intravenous administration of the developed donors in the anesthetized rats.

ASK1 INHIBITOR AND PREPARATION METHOD AND USE THEREOF

The present disclosure relates to a compound as shown in formula (II), a tautomer or a pharmaceutically acceptable salt thereof, and disclosed is the use thereof in preparing a drug for treating an ASK1-associated disease.

PYRIDINE DERIVATIVE AS ASK1 INHIBITOR AND PREPARATION METHOD AND USE THEREOF

Disclosed in the present invention are a compound as shown in formula (II), a tautomer or a pharmaceutically acceptable salt thereof, and also disclosed is the use thereof in preparing a drug for treating an ASK1-associated disease.

A THIONATION PROCESS AND A THIONATING AGENT

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N

A thionation process and a thionating agent

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.

Ruthenium catalyzed synthesis of enaminones

The Grubbs first-generation catalyst has been found to be an effective catalyst for the synthesis of enaminones by coupling thioamides with α-diazodicarbonyl compounds. The reaction is successful in converting primary, secondary, and tertiary thioamides into their corresponding enaminones. The reaction is also suitable for the synthesis of chiral enaminones.

Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.

Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.

Synthesis of ω-aminodithioesters

ω-Aminodithioester derivatives were obtained from thionolactams by reaction with an alkyl triflate followed by thiolysis with hydrogen sulfide. The presence of an electron-withdrawing group was required on the N1 position (p-nitrophenyl or benzoyl) to favor the ring opening of γ-, δ- and ε-thionolactams. In the case of β-thionolactam, activation was provided by a CF2 motif in C3 position. Georg Thieme Verlag Stuttgart.