methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate

Base Information

• Chemical Name: methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate
• CAS No.: 1219138-73-4
• Molecular Formula: C₁₆H₁₄BrNO₃
• Molecular Weight: 348.196
• Mol file: 1219138-73-4.mol

Synonyms:methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate

Chemical Property of methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate

There total 4 articles about methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate 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: 69.0%

methyl propargylcyanoacetate (1219138-77-8) + 4-bromocinnamaldeyde (49678-04-8,3893-18-3) → methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate (1219138-73-4) + methyl 2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate

Guidance literature:

methyl propargylcyanoacetate; With silica supported chiral amine-diaminopalladium complex; In chloroform; at 20 ℃; for 0.0833333h; Inert atmosphere;

4-bromocinnamaldeyde; In chloroform; at 20 ℃; for 71h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201400291

Reference yield: 67.0%

methyl propargylcyanoacetate (1219138-77-8) + 4-bromocinnamaldeyde (49678-04-8,3893-18-3) → methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate (1219138-73-4)

Guidance literature:

methyl propargylcyanoacetate; In toluene; at 20 ℃; for 0.0833333h;

4-bromocinnamaldeyde; With C₂₀H₂₇NSi; In toluene; at 20 ℃; for 24h; enantioselective reaction;

DOI:10.1002/adsc.201500100

Reference yield:

3-(4-bromophenyl)prop-2-en-1-ol (105515-33-1,130265-32-6) + methyl propargylcyanoacetate (1219138-77-8) → methyl (1R,2R)-2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate (1219138-73-4) + methyl 2-(4-bromophenyl)-1-cyano-3-formyl-4-methylcyclopent-3-enecarboxylate

Guidance literature:

3-(4-bromophenyl)prop-2-en-1-ol; With oxygen; In toluene; at 70 ℃; for 48h;

methyl propargylcyanoacetate; In toluene; at 20 ℃; for 2h; Overall yield = 52 %; enantioselective reaction;

DOI:10.1055/s-0033-1340883

upstream raw materials:

methyl propargylcyanoacetate

4-bromocinnamaldeyde

3-(4-bromophenyl)prop-2-en-1-ol

Downstream raw materials:

5-(4-bromophenyl)-4-cyano-4-(methoxycarbonyl)-2-methylcyclopent-1-enecarboxylic acid