15857-68-8

Basic information

• Product Name: 2,3-dihydro-4H-1-benzothiopyran-4-one oxime
• Synonyms: 2,3-dihydro-4H-1-benzothiopyran-4-one oxime;Thiochroman-4-one oxime;(E)-thiochroman-4-one oxime;4H-1-Benzothiopyran-4-one,2,3-dihydro-, oxime;(E)-thiochroman-4-one oxime(WXC06537)
• CAS NO: 15857-68-8
• Molecular Formula: C₉H₉NOS
• Molecular Weight: 179.23886
• EINECS: 239-979-6
• Mol File: 15857-68-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 98-100 °C
• Boiling Point: 344.3°Cat760mmHg
• Flash Point: 162°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 2.54E-05mmHg at 25°C
• Refractive Index: 1.662
• PKA: 10.79±0.20(Predicted)
• CAS DataBase Reference: 2,3-dihydro-4H-1-benzothiopyran-4-one oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydro-4H-1-benzothiopyran-4-one oxime(15857-68-8)
• EPA Substance Registry System: 2,3-dihydro-4H-1-benzothiopyran-4-one oxime(15857-68-8)

Safety Data

• Hazardous Substances Data: 15857-68-8(Hazardous Substances Data)

Usage

General Description

2,3-dihydro-4H-1-benzothiopyran-4-one oxime is a chemical compound with the molecular formula C11H11NO2S. It is a heterocyclic compound with a nitrogen and sulfur atom in its ring structure. 2,3-dihydro-4H-1-benzothiopyran-4-one oxime is also known as Trolox, a water-soluble analog of vitamin E with antioxidant properties. It has been studied for its potential therapeutic and protective effects in various diseases and conditions, including cancer, cardiovascular disease, and neurological disorders. 2,3-dihydro-4H-1-benzothiopyran-4-one oxime has shown promising results in reducing oxidative stress and inflammation in the body, making it a subject of interest in pharmaceutical and medical research.

InChI:InChI=1/C9H9NOS/c11-10-8-5-6-12-9-4-2-1-3-7(8)9/h1-4,11H,5-6H2

Upstream product

• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 5219-65-8 acide phenylthio-3 propanoique 
• 108-98-5 thiophenol 
• 3055-87-6 3-(phenylthio)propionitrile 

Downstream Products

• 1010079-97-6 (E)-thiochroman-4-one O-benzyl oxime 
• 58121-91-8 2,3,4,5-Tetrahydro-1,5-benzothiazepin hydrochloride 
• 40358-33-6 2,3,4,5-tetrahydro-benzo[b][1,4]thiazepine 
• 93192-72-4 3,4-dihydro-2H-thiochromen-4-ylamine 

Relevant articles and documents

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Design, synthesis and biological evaluation of brain penetrant benzazepine-based histone deacetylase 6 inhibitors for alleviating stroke-induced brain infarction

Histone deacetylase 6 (HDAC6) has become a promising therapeutic target for central nervous system diseases due to its more complex protein structure and biological functions. However, low brain penetration of reported HDAC6 inhibitors limits its clinical application in neurological disorders. Therefore, the benzazepine, a brain-penetrant rigid fragment, was utilized to design a series of selective HDAC6 inhibitors to improve brain bioavailability. Various synthetic strategies were applied to assemble the tetrahydro-benzazepine ring, and 22 compounds were synthesized. Among them, compound 5 showed low nanomolar potency and strong isozyme selectivity for the inhibition of HDAC6 (IC50 = 1.8 nM, 141-fold selectivity over HDAC1) with efficient binding patterns like coordination with the zinc ion and π-π stacking effect. Western blot results showed it could efficiently transport into SH-SY5Y cells and selectively enhance the acetylation level of α-tubulin with a moderate effect on Histone H3. Notably, pharmacokinetic studies demonstrated that compound 5 (brain/plasma ratio of 2.30) had an excellent ability to penetrate the blood-brain barrier of C57 mice. In male rats with transient middle cerebral artery occlusion (MCAO), compound 5 significantly reduced the cerebral infarction from 21.22% to 11.47% and alleviated neurobehavioral deficits in post-ischemic treatment, which provided a strong rationale for pursuing HDAC6-based therapies for ischemic stroke.

Regioselective synthesis of heterocycles containing nitrogen neighboring an aromatic ring by reductive ring expansion using diisobutylaluminum hydride and studies on the reaction mechanism

(Chemical Equation Presented) A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic ringswith diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an aromatic ring, including indoline, 1,2,3,4,5,6-hexahydrobenz[b]azocine, 3,4-dihydro-2H-benzo[b] [1,4]oxazine, 2,3,4,5-tetrahydrobenzo[b][1,4]thiazepine, 1,2,3,4,5,6- hexahydroazepino[3,2-b]-indole, 2,3,4,5-tetrahydro-1H-benzothieno[2,3-b]azepine, 2,3,4,5-tetrahydro-1H-benzothieno[3,2-b]-azepine, 5,6-dihydrophenanthridine, and 5,6,11,12-tetrahydrodibenz[b, f]azocine. The reaction mechanism leading to the rearrangement was investigated on the basis of the restricted Becke three-parameter plus Lee-Yang-Parr (B3LYP) density functional theory (DFT) with the 6-31G (d) basis set. It was found that the reaction proceeds through a three-centered transition state via a stepwise mechanism because the potential energy curve along the intrinsic reaction coordinate (IRC) had twomaxima (saddle points; TS1 and TS2) and the partial phenonium cation intermediate C. In addition to cyclic ketoximes fused to aromatic rings, the reactions of various cyclic and acyclic ketoximeswere examined to investigate preference of migrating group. It was found that themore electron-rich group migrated preferentially to give the corresponding secondary amines.