50886-63-0

Basic information

• Product Name: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione
• Synonyms: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione;Benzyl-3,4-dihydro-4-Methyl-1H-1,4-benzodiazepine-2,5-dione;(S)-cyclopeptine
• CAS NO: 50886-63-0
• Molecular Formula: C₁₇H₁₆N₂O₂
• Molecular Weight: 280.32
• Mol File: 50886-63-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 514.3°Cat760mmHg
• Flash Point: 264.8°C
• Appearance: /
• Density: 1.206g/cm³
• Vapor Pressure: 1.1E-10mmHg at 25°C
• Refractive Index: 1.599
• PKA: 13.20±0.40(Predicted)
• CAS DataBase Reference: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione(50886-63-0)
• EPA Substance Registry System: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione(50886-63-0)

Safety Data

• Hazardous Substances Data: 50886-63-0(Hazardous Substances Data)

Usage

Description

(4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione is a complex organic compound with a unique molecular structure. It belongs to the class of benzodiazepines, which are known for their diverse range of applications in various fields.

Uses

Used in Pharmaceutical Industry:
(4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Research and Development:
Due to its complex structure and potential applications, (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione is also used as a research compound in academic and industrial laboratories. Scientists are interested in studying its properties and exploring its potential uses in various fields, such as drug discovery and development.
Used in Chemical Synthesis:
(4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione can be used as a starting material or a key intermediate in the synthesis of other complex organic compounds. Its unique structure and reactivity make it a valuable component in the development of new chemical processes and products.

InChI:InChI=1/C17H16N2O2/c1-19-15(11-12-7-3-2-4-8-12)16(20)18-14-10-6-5-9-13(14)17(19)21/h2-10,15H,11H2,1H3,(H,18,20)/t15-/m0/s1

Upstream product

• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 19460-86-7 (N-methyl)-L-phenylalanine methyl ester hydrochloride 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 615-36-1 2-bromoaniline 
• 211567-41-8 (3S)-3,4-dihydro-2-methoxy-N-methyl-3-phenylmethyl-[1,4]benzodiazepin-5(5H)one 
• 31162-13-7 2-azidobenzoic acid 
• 34897-85-3 o-azidobenzoyl chloride 
• 196928-07-1 N-(2-azidobenzoyl)-N-methyl-L-phenylalanine methyl ester 
• 118-48-9 isatoic anhydride 
• 2439-60-3 N-methyl-L-phenylalanine methyl ester 
• 150256-42-1 2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid 

Downstream Products

• 196928-08-2 (3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione 
• 157047-96-6 (-)-benzomalvin A 
• 129-24-8 4-phenyl-3-hydroxyquinolin-2(1H)-one 
• 31965-37-4 3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione 

Relevant articles and documents

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Structure of the Dioxygenase AsqJ: Mechanistic Insights into a One-Pot Multistep Quinolone Antibiotic Biosynthesis

Multienzymatic cascades are responsible for the biosynthesis of natural products and represent a source of inspiration for synthetic chemists. The FeII/α-ketoglutarate-dependent dioxygenase AsqJ from Aspergillus nidulans is outstanding because it stereoselectively catalyzes both a ferryl-induced desaturation reaction and epoxidation on a benzodiazepinedione. Interestingly, the enzymatically formed spiro epoxide spring-loads the 6,7-bicyclic skeleton for non-enzymatic rearrangement into the 6,6-bicyclic scaffold of the quinolone alkaloid 4′-methoxyviridicatin. Herein, we report different crystal structures of the protein in the absence and presence of synthesized substrates, surrogates, and intermediates that mimic the various stages of the reaction cycle of this exceptional dioxygenase.

The first total synthesis of (-)-benzomalvin A via intramolecular Aza-Wittig reactions

The first total synthesis of (-)-benzomalvin A 1, which possesses quinazolin-4(3H)-one moiety and 1,4-benzodiazepin-5-one moiety, was described. Both of 6- and 7-membered ring skeletons were efficiently constructed by intramolecular aza-Wittig reactions as the key reactions.