20925-64-8

Basic information

• Product Name: 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one
• Synonyms: 7,8-DIMETHOXY-1,3,4,5-TETRAHYDROBENZO[D]AZEPIN-2-ONE;1,3,4,5-Tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one;7,8-DIMETHOXY-1,3-DIHYDRO-2H-BENZAZEPIN-2-ONE;1,3,4,5-Tetrahydro-7,8-dimethoxy-2H-3-Benzepin-2-one;7,8-DiMethoxy-1,3,4,5-tetrahydro-2H-benzazepin-2-one;7,8-diMethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one;7,8-diMethoxy-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one;7,8-DIMETHOXY-1,3,4,5-TETRAHYDROBENZO[D]AZEPIN-2-ONE(WXG00926)
• CAS NO: 20925-64-8
• Molecular Formula: C₁₂H₁₅NO₃
• Molecular Weight: 221.25
• EINECS: 1806241-263-5
• Mol File: 20925-64-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 438.2 °C at 760 mmHg
• Flash Point: 218.8 °C
• Appearance: /
• Density: 1.137
• Vapor Pressure: 7.05E-08mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: 2-8°C
• PKA: 15.36±0.20(Predicted)
• CAS DataBase Reference: 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one(20925-64-8)
• EPA Substance Registry System: 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one(20925-64-8)

Safety Data

• Hazardous Substances Data: 20925-64-8(Hazardous Substances Data)

Usage

General Description

7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one, also known as tetrahydroberberine, is a chemical compound derived from the alkaloid berberine found in various plants. It possesses a unique molecular structure with two methoxy groups and a tetrahydrobenzazepine ring. 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one has been studied for its potential biological activities, including anti-inflammatory, anti-bacterial, anti-fungal, and anti-cancer properties. It has also shown potential as a neuroprotective agent and for the treatment of metabolic disorders such as diabetes and obesity. Due to its diverse pharmacological activities, 7,8-Dimethoxy-1,3,4,5-tetrahydrobenzo[d]azepin-2-one is an important compound of interest in the fields of medicinal chemistry and drug discovery.

InChI:InChI=1/C12H15NO3/c1-15-10-5-8-3-4-13-12(14)7-9(8)6-11(10)16-2/h5-6H,3-4,7H2,1-2H3,(H,13,14)

Upstream product

• 14301-31-6 2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 82988-55-4 N-cyclohexylidene-2-(3,4-dimethoxyphenyl)ethylamine 
• 97185-46-1 N-(cyclohex-1-enyl)-N-<2-(3,4-dimethoxyphenyl)ethyl>-α-(methylthio)acetamide 
• 82988-56-5 N-(cyclohex-1-enyl)-N-<2-(3,4-dimethoxyphenyl)ethyl>-α-(methylsulphinyl)acetamide 
• 2472-13-1 6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-one 
• 146858-74-4 N-(tert-butoxycarbonyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one 
• 4721-98-6 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 73954-34-4 N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide 
• 55171-76-1 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one 
• 73942-87-7 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 
• 97185-50-7 N-(4-benzyloxycyclohex-1-enyl)-N-<2-(3,4-dimethoxyphenyl)ethyl>-α-(methylsulphinyl)acetamide 
• 97185-49-4 N-(4-benzyloxycyclohex-1-enyl)-N-<2-(3,4-dimethoxyphenyl)ethyl>-α-(methylthio)acetamide 

Downstream Products

• 85175-67-3 zatebradine 
• 37462-47-8 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 14165-90-3 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride 
• 148849-67-6 ivabradine hydrochloride 
• 146858-74-4 N-(tert-butoxycarbonyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one 
• 148849-68-7 3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one hydrochloride 
• 155974-00-8 ivabradine 
• 1246638-04-9 3-(7,8-Dimethoxy-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-propanenitrile 
• 85175-65-1 7,8-dimethoxy-3-(3-chloropropyl)-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one 
• 119918-74-0 3-[(N-(3-(3-Methyl-phenoxy)-propyl)-hexahydro-azepin-3-yl)methyl]-7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepinehydrochloride 
• 109859-79-2 3-[(N-(2-(3,4-Dimethoxy-phenyl)-ethyl)-hexahydro-azepin-3-yl)-methyl]-7,8-dimethoxy-1,3,4, 5-tetrahydro-2H-3-benzazepin-2-one-hydrochloride 
• 119918-72-8 3-[(N-(2-(4-Methoxy-phenyl)-ethyl)-hexahydro-azepin-3-yl)methyl]-7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepinehydrochloride 

Relevant articles and documents

Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin: Via iridium-catalyzed asymmetric hydrogenation

Phosphine-oxazoline (PHOX) ligands are a very important class of privileged ligands in asymmetric catalysis. A series of highly rigid oxa-spiro phosphine-oxazoline (O-SIPHOX) ligands based on O-SPINOL was synthesized efficiently, and their iridium complexes were synthesized by coordination of the O-SIPHOX ligands to [Ir(cod)Cl]2 in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asymmetric hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol.

1,2,4,5-Tetrahydro-3H-benzazepine compounds, a process for their preparation and pharmaceutical compositions containing them

Compounds of formula (I): wherein: R1 represents a hydrogen atom or a group selected from cycloalkyl, benzyl and optionally substituted alkyl,R2, R3, R4 and R5 each represent a hydrogen atom or a hydroxy, methyl, —OSO2R10, —OCOR10 or optionally substituted alkoxy group, or R2 and R3, or R3 and R4, or R4 and R5 together form a group —O—(CH2)q—O—, —O—CH═CH—O— or —O—CH═CH—,R6, R7, R8 and R9 each represent a hydrogen atom or an alkoxy group, or R6 and R7, or R7 and R8, or R8 and R9 together form a group —O—(CH2)q—O—-,R10 represents a group selected from linear or branched C1-C6alkoxy, NR11R′11 and optionally substituted alkyl,R11 and R′11 each represent a hydrogen atom or an alkyl group, or R11 and R′1 together with the nitrogen atom carrying them form an optionally substituted, monocyclic or bicyclic, nitrogen-containing heterocycle,X represents O, NH or CH2,m and p each represent 0 or 1,n and q each represent 1 or 2, in racemic form or in the form of optical isomers,and also addition salts thereof with a pharmaceutically acceptable acid. Medicinal products containing the same which are useful in treating various pathologies.