Methyl-4,4-dimethoxy-2-(3-nitrobenzylidene)-acetoacetate

Base Information

• Chemical Name: Methyl-4,4-dimethoxy-2-(3-nitrobenzylidene)-acetoacetate
• CAS No.: 75530-05-1
• Molecular Formula: C₁₄H₁₅NO₇
• Molecular Weight: 309.276
• DSSTox Substance ID: DTXSID80439758
• Nikkaji Number: J243.029K
• Wikidata: Q82255822
• Mol file: 75530-05-1.mol

Synonyms:METHYL-4,4-DIMETHOXY-2-(3-NITROBENZYLIDENE)-ACETOACETATE;67448-15-1;METHYL (2Z)-4,4-DIMETHOXY-2-[(3-NITROPHENYL)METHYLIDENE]-3-OXOBUTANOATE;DTXSID80439758;WJMUEQYQRJJCRC-FLIBITNWSA-N;2-(Dimethoxyacetyl)-3-(3-nitrophenyl)acrylic acid methyl ester

Chemical Property of Methyl-4,4-dimethoxy-2-(3-nitrobenzylidene)-acetoacetate

Chemical Property:

• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 309.08485182
• Heavy Atom Count: 22
• Complexity: 451

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(C(=O)C(=CC1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)OC
• Isomeric SMILES: COC(C(=O)/C(=C/C1=CC(=CC=C1)[N+](=O)[O-])/C(=O)OC)OC

Technology Process of Methyl-4,4-dimethoxy-2-(3-nitrobenzylidene)-acetoacetate

There total 1 articles about Methyl-4,4-dimethoxy-2-(3-nitrobenzylidene)-acetoacetate 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:

4,4-dimethoxy-3-oxo-butyric acid methyl ester (60705-25-1) + 3-nitro-benzaldehyde (99-61-6) → 4,4-Dimethoxy-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester (75530-05-1)

Guidance literature:

DOI:10.1016/S0040-4039(00)91976-2

Reference yield: 16.0%

(Z)-3-Amino-but-2-enoic acid 2-cyano-ethyl ester (193539-61-6) + 4,4-Dimethoxy-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester (75530-05-1) → 5-(2-cyanoethyl) 3-methyl 2-(dimethoxymethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate + (+/-)-(2S,3R,4S)-5-(2-cyanoethyl) 3-methyl 2-(dimethoxymethyl)-2-hydroxy-6-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydropyridine-3,5-dicarboxylate + (+/-)-(2R,3S,4S)-5-(2-cyanoethyl) 3-methyl 2-(dimethoxymethyl)-2-hydroxy-6-methyl-4-(3-nitrophenyl)-1,2,3,4-tetrahydropyridine-3,5-dicarboxylate

Guidance literature:

With pyridinium acetate; In isopropyl alcohol; Yields of byproduct given; Heating;

DOI:10.1016/S0040-4039(00)91976-2

Reference yield:

4,4-Dimethoxy-2-[1-(3-nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid methyl ester (75530-05-1) → 5-(2-cyanoethyl) 3-ethyl 2-(diethoxymethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine acetate / propan-2-ol / Heating

2: camphorsulfonic acid / methanol

With camphor-10-sulfonic acid; pyridinium acetate; In methanol; isopropyl alcohol;

DOI:10.1016/S0040-4039(00)91976-2

upstream raw materials:

4,4-dimethoxy-3-oxo-butyric acid methyl ester

3-nitro-benzaldehyde