1,2,5-Trimethyl-2,6-diazabicyclo[2.2.0]hex-5-en-3-one

Base Information

• Chemical Name: 1,2,5-Trimethyl-2,6-diazabicyclo[2.2.0]hex-5-en-3-one
• CAS No.: 76599-91-2
• Molecular Formula: C7H10N2O
• Molecular Weight: 138.169
• DSSTox Substance ID: DTXSID00527348
• Nikkaji Number: J854.410G
• Mol file: 76599-91-2.mol

Synonyms:76599-91-2;1,2,5-Trimethyl-2,6-diazabicyclo[2.2.0]hex-5-en-3-one;DTXSID00527348

Chemical Property of 1,2,5-Trimethyl-2,6-diazabicyclo[2.2.0]hex-5-en-3-one

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 138.079312947
• Heavy Atom Count: 10
• Complexity: 246

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2(C1C(=O)N2C)C

Technology Process of 1,2,5-Trimethyl-2,6-diazabicyclo[2.2.0]hex-5-en-3-one

There total 2 articles about 1,2,5-Trimethyl-2,6-diazabicyclo[2.2.0]hex-5-en-3-one 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: 33.0%

2,3,6-trimethyl-4(3H)-pyrimidin-4-one (32363-51-2) → 1,3,6-Trimethyl-5-oxo-2,6-diazabicyclo<2.2.0>hex-2-ene (76599-91-2)

Guidance literature:

for 8h; Irradiation;

DOI:10.1021/jo00388a022

Reference yield:

N-Methyl-3-<(methoxyethylidene)amino>-2-butenamide (73645-42-8) → 1,3,6-Trimethyl-5-oxo-2,6-diazabicyclo<2.2.0>hex-2-ene (76599-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 percent / NaOCH₃ / methanol / 4 h

2: 32 percent Spectr_. / liquid ammonia; diethyl ether / 9 h / -40 °C / Irradiation

With sodium methylate; In methanol; diethyl ether; ammonia;

DOI:10.1021/jo00322a003

Reference yield:

1,3,6-Trimethyl-5-oxo-2,6-diazabicyclo<2.2.0>hex-2-ene (76599-91-2) → 2,3,6-trimethyl-4(3H)-pyrimidin-4-one (32363-51-2) + N-methylacetoacetamide (20306-75-6) + (Z)-2-acetyl-3-amino-N-methylbut-2-enamide (99699-39-5) + (Z)-N-acetyl-N-methyl-3-aminobut-2-enamide (99699-36-2)

Guidance literature:

Product distribution; CD₃CN, H₂O; acetone, H₂O;

upstream raw materials:

2,3,6-trimethyl-4(3H)-pyrimidin-4-one

N-Methyl-3-<(methoxyethylidene)amino>-2-butenamide

Downstream raw materials:

2,3,6-trimethyl-4(3H)-pyrimidin-4-one

N-methylacetoacetamide

(Z)-2-acetyl-3-amino-N-methylbut-2-enamide

(Z)-N-acetyl-N-methyl-3-aminobut-2-enamide