2,5-Dimethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate

Base Information

• Chemical Name: 2,5-Dimethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate
• CAS No.: 148528-45-4
• Molecular Formula: C15H15 N O6
• Molecular Weight: 305.287
• DSSTox Substance ID: DTXSID70406656
• Nikkaji Number: J729.023C
• Wikidata: Q82211728
• Mol file: 148528-45-4.mol

Synonyms:148528-45-4;2,5-DIMETHYL 1-BENZYL-3,4-DIHYDROXY-1H-PYRROLE-2,5-DICARBOXYLATE;dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate;dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate;Dimethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate;1-Benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester;SCHEMBL182807;Dimethyl 1-benzyl-3,4-dihydroxy-pyrrole-2,5-dicarboxylate;DTXSID70406656;AKOS025211810;AB52582;FT-0761665;J-008481;Dimethyl1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate

Chemical Property of 2,5-Dimethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate

Chemical Property:

• PSA: 97.99000
• LogP: 1.52080
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 305.08993720
• Heavy Atom Count: 22
• Complexity: 381

Purity/Quality:

98%min ^*data from raw suppliers

Dimethyl1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C(=C(N1CC2=CC=CC=C2)C(=O)OC)O)O
• Uses: Dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate

Technology Process of 2,5-Dimethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate

There total 6 articles about 2,5-Dimethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate 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: 88.0%

Dimethyl oxalate (553-90-2) + dimethyl 2,2′-(benzylazanediyl)diacetate (6175-26-4) → dimethyl-1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (148528-45-4)

Guidance literature:

Dimethyl oxalate; With sodium hydride; In tetrahydrofuran; mineral oil; Inert atmosphere; Reflux;

dimethyl 2,2′-(benzylazanediyl)diacetate; In tetrahydrofuran; mineral oil; Inert atmosphere; Reflux;

DOI:10.3987/COM-08-S(F)89

Reference yield: 77.0%

dimethyl 2,2′-(benzylazanediyl)diacetate (6175-26-4) + oxalic acid diethyl ester (95-92-1) → dimethyl-1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (148528-45-4)

Guidance literature:

With sodium methylate; In methanol; for 15h; Reflux; Inert atmosphere;

DOI:10.1007/s00706-008-0057-7

Reference yield: 2.0%

dimethyl 3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate (1632-19-5) + benzyl bromide (100-39-0) → dimethyl-1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (148528-45-4) + dimethyl 1-benzyl-3,4-dibenzyloxypyrrole-2,5-dicarboxylate

Guidance literature:

With potassium carbonate; In acetone; for 3.5h; Heating;

DOI:10.1055/s-1995-3993

upstream raw materials:

dimethyl 2,2′-(benzylazanediyl)diacetate

oxalic acid diethyl ester

Dimethyl oxalate

dimethyl 3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate

Downstream raw materials:

dimethyl 1-benzyl-3,4-diethoxypyrrole-2,5-dicarboxylate

dimethyl 1-benzyl-3,4-ethylenedioxypyrrole-2,5-dicarboxylate

dimethyl 1-benzyl-3,4-dihexadecyloxypyrrole-2,5-dicarboxylate

dimethyl 14-benzyl-6,6,7,7-tetramethyl-3,4,6,7,10,11-hexahydro-2H,9H,14H-[1,4,8,11]tetraoxacyclotetradecino[2,3-c]pyrrole-13,15-dicarboxylate

Refernces

• 1、 Dey, Sanjeev K.,Lightner, David A.. "Water-soluble xanthobilirubinic acids?". experimental part. p. 161 - 170. Retrieved 2010/04/02.
• 2、 Murashima, Takashi,Wakamori, Naoko,Uchihara, Yuki,Ogawa, Takujl,Uno, Hidemitsu,Ono, Noboru. "A new route to porphyrins substituted with long alkoxy groups, attempts to prepare the discotic liquid crystals". . p. 165 - 171. Retrieved 2007/10/03.