3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione

Base Information

Chemical Name:3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione
CAS No.:31965-37-4
Molecular Formula:C17H14 N2 O2
Molecular Weight:278.3053
Hs Code.:
DSSTox Substance ID:DTXSID10953851
Wikidata:Q27139509
Mol file:31965-37-4.mol

Synonyms:1H-1,4-Benzodiazepine-2,5-dione,3-benzylidene-3,4-dihydro-4-methyl- (8CI); 3,10-Dehydrocyclopeptine;Cyclopeptine, dehydro-; Dehydrocyclopeptine

Suppliers and Price of 3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Dehydrocyclopeptine
1mg
$ 426.00

TRC
Dehydrocyclopeptine(MixtureofConformers)
1mg
$ 155.00

Cayman Chemical
Dehydrocyclopeptine ≥99%
5mg
$ 852.00

Cayman Chemical
Dehydrocyclopeptine ≥99%
1mg
$ 190.00

Total 6 raw suppliers

Chemical Property of 3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione

Chemical Property:

Vapor Pressure:5.99E-12mmHg at 25°C
Boiling Point:545.3°Cat760mmHg
Flash Point:283.6°C
PSA：54.86000
Density:1.254g/cm³
LogP:1.33670
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:278.105527694
Heavy Atom Count:21
Complexity:452

Purity/Quality:

98%Min ^*data from raw suppliers

Dehydrocyclopeptine ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CN1C(=CC2=CC=CC=C2)C(=O)NC3=CC=CC=C3C1=O
Description Dehydrocyclopeptine is an intermediate in the synthesis of benzodiazepine alkaloids in Penicillium. It is formed when the 3S-isomer of cyclopeptine undergoes reversible transformation by cyclopeptine dehydrogenase to displace hydrogens from the 3- and 10-positions of the benzodiazepine core.
Uses Dehydrocyclopeptine is a benzodiazepine metabolite responsible for biosynthesis of cyclopeptine synthetase. It is also used in vitro evaluation of photoprotective potential of quinolinic alkaloids isolated from antarctic marine fungus Penicillium echinulatum for topical use. Dehydrocyclopeptine is a benzodiazepine metabolite produced by a number of species of Penicillium. While there is little literature about the metabolite, there is considerable interest in the enzymes responsible for the biosynthesis of the benzodiazepine nucleus, cyclopeptine synthetase.

Technology Process of 3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione

There total 4 articles about 3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 25.0%

: 100-52-7
benzaldehyde

: 3415-35-8
4-methyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-dione

: 31965-37-4
3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Guidance literature:: With sodium acetate; acetic anhydride; for 3h; Reflux;
DOI:10.1021/jacs.6b05400

Reference yield:

: 118-48-9
isatoic anhydride

: 31965-37-4
3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / water / 14 h / 20 °C

1.2: 6 h / 125 °C

2.1: acetic anhydride; sodium acetate / 3 h / Reflux

With sodium acetate; acetic anhydride; triethylamine; In water;
DOI:10.1021/jacs.6b05400

Reference yield:

: 150256-42-1
2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid

: 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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2-hydroxyethanethiol; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 0.33 h / 20 °C

1.2: 6 h / 20 °C

2.1: fungal dioxygenase AsqJ; α-ketoglutaric acid; ascorbic acid; iron(II) sulfate; oxygen / N,N-dimethyl-formamide / 3 h / Enzymatic reaction

With α-ketoglutaric acid; oxygen; fungal dioxygenase AsqJ; iron(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol; ascorbic acid; In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide;
DOI:10.1002/anie.202017086