17775-01-8

Basic information

• Product Name: 2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine
• Synonyms: 2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine;2,3,4,5-tetrahydro-1,4-benzoxazepine(SALTDATA: FREE)
• CAS NO: 17775-01-8
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• Mol File: 17775-01-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 254.458 °C at 760 mmHg
• Flash Point: 95.39 °C
• Appearance: /
• Density: 1.058 g/cm³
• Vapor Pressure: 0.017mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine(17775-01-8)
• EPA Substance Registry System: 2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine(17775-01-8)

Safety Data

• Hazardous Substances Data: 17775-01-8(Hazardous Substances Data)

Usage

General Description

2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine is a chemical compound with a bicyclic structure containing a benzene ring fused to a seven-membered oxazepine ring. It is a heterocyclic compound with potential pharmaceutical applications and is also referred to as benzo[f][1,4]oxazepine. 2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine has been investigated for its potential use in the development of drugs for various therapeutic areas, including neurological and psychiatric disorders. Its unique structure and pharmacological properties make it a topic of interest in medicinal chemistry and drug discovery research.

InChI:InChI=1/C9H11NO/c1-2-4-9-8(3-1)7-10-5-6-11-9/h1-4,10H,5-7H2

Upstream product

• 703-51-5 2,3-dihydro-1,4-benzoxazepin-5(4H)-one 
• 5755-05-5 7-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 6630-33-7 ortho-bromobenzaldehyde 
• 251326-32-6 2-((2-bromobenzyl)amino)ethan-1-ol 
• 90-02-8 salicylaldehyde 
• 34844-79-6 methyl 2-(2-cyanophenoxy)ethanoate 
• 34844-80-9 4,5-dihydro-1,4-benzoxazepin-3(2H)-one 

Downstream Products

• 21492-58-0 4-(2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-1-(4-fluoro-phenyl)-butan-1-one 
• 1426385-50-3 C₁₈H₁₄F₃NO₃ 

Relevant articles and documents

[1,5]-Hydride shift-cyclization versus C(sp2)-H functionalization in the knoevenagel-cyclization domino reactions of 1,4- And 1,5-Benzoxazepines

Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp3)-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp2)-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative had a 6.98 μM IC50 value.

N-Atom Deletion in Nitrogen Heterocycles

Excising the nitrogen in secondary amines, and coupling the two residual fragments is a skeletal editing strategy that can be used to construct molecules with new skeletons, but which has been largely unexplored. Here we report a versatile method of N-atom excision from N-heterocycles. The process uses readily available N-heterocycles as substrates, and proceeds by N-sulfonylazidonation followed by the rearrangement of sulfamoyl azide intermediates, providing various cyclic products. Examples are provided of deletion of nitrogen from natural products, synthesis of chiral O-heterocycles from commercially available chiral β-amino alcohols, formal inert C?H functionalization through a sequence of N-directed C?H functionalization and N-atom deletion reactions in which the N-atom can serve as a traceless directing group.

Process Development and Scale-Up of a Benzoxazepine-Containing Kinase Inhibitor

The benzoxazepine core is present in several kinase inhibitors, including the mTOR inhibitor 1. The process development for a scalable synthesis of 7-bromobenzoxazepine and the telescoped synthesis of 1 are reported. Compound 1 consists of three chemicall