Ethyl 4-(tert-butoxycarbonylamino)cinnamate

Base Information

• Chemical Name: Ethyl 4-(tert-butoxycarbonylamino)cinnamate
• CAS No.: 144072-31-1
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.347
• DSSTox Substance ID: DTXSID601160229
• Mol file: 144072-31-1.mol

Synonyms:BBSWQBQZKDJGRV-UHFFFAOYSA-N;DTXSID601160229;AKOS017520700;ethyl 4-(tert-butoxycarbonylamino)cinnamate;ethyl 4-(tert-butoxycarbonyl-amino)cinnamate;Ethyl 3-[4-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-2-propenoate;144072-31-1

Chemical Property of Ethyl 4-(tert-butoxycarbonylamino)cinnamate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 376

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=CC=C(C=C1)NC(=O)OC(C)(C)C

Technology Process of Ethyl 4-(tert-butoxycarbonylamino)cinnamate

There total 11 articles about Ethyl 4-(tert-butoxycarbonylamino)cinnamate 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: 83.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 4-((tert-butoxycarbonyl)amino)benzaldehyde (144072-30-0) → ethyl 3-<4-phenyl>propenoate (144072-31-1,239088-81-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1002/cmdc.201900281

Reference yield: 72.0%

diazoacetic acid ethyl ester (623-73-4) + 4-((tert-butoxycarbonyl)amino)benzaldehyde (144072-30-0) → ethyl 3-<4-phenyl>propenoate (144072-31-1,239088-81-4)

Guidance literature:

With copper(l) iodide; triphenylphosphine; In tetrahydrofuran; at 60 ℃; for 16h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.200800381

Reference yield: 63.0%

ethyl acrylate (140-88-5,9003-32-1) + 4-tert-butoxycarbonylamino-benzenediazonium; trifluoro-acetate → ethyl 3-<4-phenyl>propenoate (144072-31-1,239088-81-4)

Guidance literature:

With palladium diacetate; In ethanol; dichloromethane;

DOI:10.1002/(SICI)1099-0690(199906)1999:6<1357::AID-EJOC1357>3.0.CO;2-P

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

4-((tert-butoxycarbonyl)amino)benzaldehyde

ethyl acrylate

N-(tert-butoxycarbonyl)-1,4-phenylenediamine

Downstream raw materials:

ethyl 3-<4-phenyl>-5,6-dibromohexanoate

3-<4-phenyl>-5-hexynoic acid

4-(4-guanidinophenyl)-6-(E)-(iodomethylidene)tetrahydro-2-pyranone

3-(4-guanidinophenyl)-5-hexynoic acid

Refernces

• 1、 Lebel, Helene,Davi, Michael,Roy, Marie-Noelle,Zeghida, Walid,Charette, Andre B.. "Olefination reactions using tetraarylphosphonium (TAP)-supported phosphorus ylides". experimental part. p. 2275 - 2280. Retrieved 2011/09/15.
• 2、 Lebel, Helene,Davi, Michael. "Diazo reagents in copper(I)-catalyzed olefination of aldehydes". supporting information; experimental part. p. 2352 - 2358. Retrieved 2009/10/02.