24541-01-3

Basic information

• Product Name: Chroman-4-One Oxime
• Synonyms: Chroman-4-One Oxime;(E)-Chroman-4-One Oxime;4H-1-Benzopyran-4-one, 2,3-dihydro-, oxime;N-Hydroxy-2,3-dihydro-4H-chromen-4-imine;(E)-Chroman-4-One Oxime(WXC02425)
• CAS NO: 24541-01-3
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• Mol File: 24541-01-3.mol

Chemical Properties

• Melting Point: 138 °C
• Boiling Point: 323.7±22.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• PKA: 10.83±0.20(Predicted)
• CAS DataBase Reference: Chroman-4-One Oxime(CAS DataBase Reference)
• NIST Chemistry Reference: Chroman-4-One Oxime(24541-01-3)
• EPA Substance Registry System: Chroman-4-One Oxime(24541-01-3)

Safety Data

• Hazardous Substances Data: 24541-01-3(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
Chroman-4-One Oxime is utilized as a key component in the development of potential drug candidates. Its chemical structure and properties make it a valuable asset in medicinal chemistry, contributing to the creation of new and important chemical entities for therapeutic applications.
Used in Pharmaceutical Synthesis:
Chroman-4-One Oxime serves as an intermediate in the synthesis of various pharmaceuticals, playing a crucial role in the production of medications that address a range of health conditions.
Used in Research and Laboratory Settings:
Chroman-4-One Oxime is also employed as a reagent in research and laboratory settings, where it aids in organic synthesis and the exploration of new chemical reactions and processes. Its presence in these environments underscores its importance in advancing scientific knowledge and innovation.

Upstream product

• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 60633-78-5 2-(2-bromoethoxy)benzaldehyde 
• 1481-93-2 4-hydroxychroman 
• 5470-11-1 hydroxylamine hydrochloride 
• 1304141-71-6 3,4-dihydro-N-hydroxy-2H-1-benzopyran-4-amine 
• 108-95-2 phenol 
• 3055-86-5 3-phenoxypropionitrile 
• 7170-38-9 3-phenoxypropanoic acid 

Downstream Products

• 7160-97-6 2,3,4,5-tetrahydro-1,5-benzoxazepine 
• 703-51-5 2,3-dihydro-1,4-benzoxazepin-5(4H)-one 
• 704-48-3 2,3,4,5-tetrahydro-1,5-benzoxazepin-4-one 
• 53981-38-7 chroman-4-amine 
• 192461-83-9 N-(chroman-4-ylidene)-P,P-diphenylphosphinamide 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 90609-63-5 3,4-dihydro-2H-chromene-4-amine hydrochloride 
• 222415-34-1 N-(2H-chromen-4-yl)acetamide 
• 1393824-62-8 N-(3-benzoyl-2H-chromen-4-yl)acetamide 
• 1393824-63-9 N-[3-(4-methyl-benzoyl)-2H-chromen-4-yl]acetamide 
• 1393824-64-0 N-[3-(4-methoxy-benzoyl)-2H-chromen-4-yl]acetamide 
• 1393824-65-1 N-[3-(4-chloro-benzoyl)-2H-chromen-4-yl]acetamide 
• 1393824-66-2 N-[3-(4-fluoro-benzoyl)-2H-chromen-4-yl]acetamide 
• 1393824-67-3 N-[3-(2-methyl-benzoyl)-2H-chromen-4-yl]acetamide 

Relevant articles and documents

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InBr3- and AgOTf-catalyzed beckmann rearrangement of (E)-benzoheterocyclic oximes

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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.

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