Antibiotic DC 81

Base Information

• Chemical Name: Antibiotic DC 81
• CAS No.: 81307-24-6
• Deprecated CAS: 89824-22-6
• Molecular Formula: C₁₃H₁₄N₂O₃
• Molecular Weight: 246.266
• DSSTox Substance ID: DTXSID701001913
• Nikkaji Number: J724.164J
• Mol file: 81307-24-6.mol

Synonyms:Antibiotic DC 81;DC 81;81307-24-6;3-hydroxy-2-methoxy-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one;SCHEMBL14421001;DTXSID701001913;(+)-1,2,3,11a-Tetrahydro-8-hydroxy-7-methoxy-5H-pyrrolo(2,1-c)(1,4)benzodiazepin-5-one;5H-Pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 1,2,3,11a-tetrahydro-8-hydroxy-7-methoxy-, (+)-;8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Chemical Property of Antibiotic DC 81

Chemical Property:

• Vapor Pressure: 1.88E-11mmHg at 25°C
• Refractive Index: 1.675
• Boiling Point: 520.5°Cat760mmHg
• Flash Point: 268.6°C
• PSA: 62.13000
• Density: 1.43g/cm³
• LogP: 1.09480
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 246.10044231
• Heavy Atom Count: 18
• Complexity: 371

Purity/Quality:

95% ^*data from raw suppliers

(11AS)-1,2,3,11A-TETRAHYDRO-8-HYDROXY-7-METHOXY-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPIN-5-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=O)N3CCCC3C=N2)O

Technology Process of Antibiotic DC 81

There total 45 articles about Antibiotic DC 81 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: 91.0%

8-benzyl DC-81 (127810-79-1) → (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (81307-24-6,123355-42-0,89824-22-6)

Guidance literature:

With cyclohexa-1,4-diene; palladium on activated charcoal; In ethanol; at 20 ℃; for 2.5h;

DOI:10.1055/s-2004-834821

Reference yield: 83.0%

(2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal (140647-03-6) → (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (81307-24-6,123355-42-0,89824-22-6)

Guidance literature:

With calcium carbonate; mercury dichloride; In water; acetonitrile; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88134-5

Reference yield: 75.0%

(S)-1-(2-Azido-4-hydroxy-5-methoxy-benzoyl)-pyrrolidine-2-carbaldehyde (166451-19-0) → (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (81307-24-6,123355-42-0,89824-22-6)

Guidance literature:

With aluminium(III) triflate; sodium iodide; In acetonitrile; at 20 ℃; for 0.75h; chemoselective reaction;

DOI:10.1002/chem.200900853

upstream raw materials:

8-benzyl DC-81

(2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde dimethyl acetal

(2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal

(11aS)-8-hydroxy-7-methoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo<2,1-c><1,4>benzodiazepine-5-one

Downstream raw materials:

7-methoxy-8-[5-(2-phenylethynyl-phenyl)-pent-4-ynyloxy]-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one

7-methoxy-8-[3-(2-phenylethynyl-phenyl)-prop-2-ynyloxy]-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one

7-methoxy-8-{(Z)-4-[4-(2-phenylethynyl-phenyl)-but-3-ynyloxy]-but-2-enyloxy}-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one

7-methoxy-8-{(Z)-4-[3-(2-phenylethynyl-phenyl)-prop-2-ynyloxy]-but-2-enyloxy}-1,2,3,11a-tetrahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one