(1Z)-2-Diazonio-3-methoxy-3-oxo-1-phenylprop-1-en-1-olate

Base Information

• Chemical Name: (1Z)-2-Diazonio-3-methoxy-3-oxo-1-phenylprop-1-en-1-olate
• CAS No.: 1807-69-8
• Molecular Formula: C10H9N2O3+
• Molecular Weight: 204.185
• NSC Number: 19798
• DSSTox Substance ID: DTXSID30716182
• Nikkaji Number: J3.196.557H
• Mol file: 1807-69-8.mol

Synonyms:NSC 19798;1807-69-8;methyl benzoyl-diazoacetate;DTXSID30716182;NSC19798;NSC-19798;alpha-Diazo-beta-oxobenzenepropionic acid methyl ester;(1Z)-2-Diazonio-3-methoxy-3-oxo-1-phenylprop-1-en-1-olate

Chemical Property of (1Z)-2-Diazonio-3-methoxy-3-oxo-1-phenylprop-1-en-1-olate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 204.05349212
• Heavy Atom Count: 15
• Complexity: 313

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=[N+]=[N-])C(=O)C1=CC=CC=C1

Technology Process of (1Z)-2-Diazonio-3-methoxy-3-oxo-1-phenylprop-1-en-1-olate

There total 7 articles about (1Z)-2-Diazonio-3-methoxy-3-oxo-1-phenylprop-1-en-1-olate 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: 93.0%

4-toluenesulfonyl azide (941-55-9) + methyl 3-oxo-3-phenylpropionate (614-27-7) → 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester (1807-69-8)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1002/ejoc.201601598

Reference yield: 90.0%

methyl 3-oxo-3-phenylpropionate (614-27-7) → 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester (1807-69-8)

Guidance literature:

With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; at 0 - 20 ℃;

DOI:10.1039/d0ob00800a

Reference yield:

acetophenone (98-86-2) → 2-diazo-3-oxo-3-phenyl-propionic acid methyl ester (1807-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; toluene / 0.5 h / Inert atmosphere; Reflux

2.1: triethylamine / acetonitrile / 0.08 h / Inert atmosphere

2.2: 2.5 h / 20 °C / Inert atmosphere

With sodium hydride; triethylamine; In toluene; acetonitrile; mineral oil;

DOI:10.1021/acs.orglett.6b01933

upstream raw materials:

Benzoyl bromide

methyl diazoacetate

2-hydroxyimino-3-oxo-3-phenyl-propionic acid methyl ester

benzoyl chloride

Downstream raw materials:

dimethyl 2-phenylmalonate

3-oxo-2-phenyl-acrylic acid methyl ester

4-oxo-1,2,2,3-tetraphenyl-azetidine-3-carboxylic acid methyl ester

methyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate