Ethyl alpha-cyano-beta-phenylcinnamate

Base Information

• Chemical Name: Ethyl alpha-cyano-beta-phenylcinnamate
• CAS No.: 14533-87-0
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.225
• European Community (EC) Number: 217-972-9
• NSC Number: 8904
• DSSTox Substance ID: DTXSID701275289
• Nikkaji Number: J1.245.708A
• Mol file: 14533-87-0.mol

Synonyms:14533-87-0;2-Propenoic acid, 2-cyano-3-phenyl-, ethyl ester, (2Z)-;Ethyl 2-cyanocinnamate;ethyl z-cyano-cinnamate;Ethyl2-cyano-3-phenylacrylate;SCHEMBL988236;NSC8904;DTXSID701275289;(z)-ethyl2-cyano-3-phenylacrylate;NSC-8904;(z)-ethyl 2-cyano-3-phenylacrylate;CAK122472;MFCD00550088;AKOS000499611;alpha-Cyanoallocinnamic acid ethyl ester;2-Cyano-3-phenyl-acrylic acid ethyl ester;ethyl (2Z)-2-cyano-3-phenylprop-2-enoate;ethyl (Z)-2-cyano-3-phenyl-prop-2-enoate;Ethyl .alpha.-cyano-.beta.-phenylcinnamate;Ethyl (2Z)-2-cyano-3-phenyl-2-propenoate;A814361

Chemical Property of Ethyl alpha-cyano-beta-phenylcinnamate

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 292

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=CC=C1)C#N
• Isomeric SMILES: CCOC(=O)/C(=C\C1=CC=CC=C1)/C#N

Technology Process of Ethyl alpha-cyano-beta-phenylcinnamate

There total 6 articles about Ethyl alpha-cyano-beta-phenylcinnamate 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: 99.7%

benzaldehyde (100-52-7) + ethyl 2-cyanoacetate (105-56-6) → (Z)-ethyl 2-cyano-3-phenylacrylate (14533-87-0)

Guidance literature:

With alkylated poly(propylene imine) dendrimer;

DOI:10.1246/cl.2005.286

Reference yield: 94.0%

N-benzylidenephenylsulfonamide (13909-34-7) + ethyl 2-cyanoacetate (105-56-6) → (Z)-ethyl 2-cyano-3-phenylacrylate (14533-87-0)

Guidance literature:

With triethylamine; In chloroform; for 3h; Ambient temperature;

DOI:10.1080/00397919408011202

Reference yield: 85.0%

benzaldehyde (100-52-7) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyano-3-phenylpropanoate (6731-58-4) + (Z)-ethyl 2-cyano-3-phenylacrylate (14533-87-0)

Guidance literature:

benzaldehyde; ethyl 2-cyanoacetate; In methanol; for 1h;

With hydrogen; 1-phosphanorbornadiene-rhodium; silica matrix; In methanol; for 12h; under 5250.42 Torr;

DOI:10.1039/b403491k

upstream raw materials:

benzaldehyde

ethyl 2-cyanoacetate

N-benzylidenephenylsulfonamide

2-phenyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine

Downstream raw materials:

3-Amino-5-cyclopropyl-biphenyl-2,4-dicarbonitrile

6-hydroxy-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile

4-phenyl-2-oxo-3-(1-pyridino)-5-cyano-3,4-trans-1,2,3,4-tetrahydro-6-pyridinolate

2-Amino-3-benzyl-6-cyano-7-oxo-5-phenyl-4,5,6,7-tetrahydropyrazolo<1,5-a>pyrimidine

Refernces

• 1、 Macquarrie, Duncan J.,Jackson, Dominic B.. "Aminopropylated MCMs as base catalysts: A comparison with aminopropylated silica". . p. 1781 - 1782. Retrieved 1997.
• 2、 Forsyth, Stewart A.,Froehlich, Ute,Goodrich, Peter,Gunaratne, H. Q. Nimal,Hardacre, Christopher,McKeown, Angela,Seddon, Kenneth R.. "Functionalised ionic liquids: Synthesis of ionic liquids with tethered basic groups and their use in Heck and Knoevenagel reactions". . p. 723 - 731. Retrieved 2010.
• 3、 Zajac Jr.,Walters,Buzby,Gagnon,Labroli. "N-Benzylidenebenzenesulfonamide as a benzaldehyde equivalent in the Knoevenagel reaction". . p. 427 - 432. Retrieved 1994.
• 4、 Ding, Yan,Ni, Xiao,Gu, Mengjie,Li, Shuang,Huang, He,Hu, Yi. "Knoevenagel condensation of aromatic aldehydes with active methylene compounds catalyzed by lipoprotein lipase". . p. 101 - 104. Retrieved 2015/02/19.
• 5、 Gianotti, Enrica,Diaz, Urbano,Velty, Alexandra,Corma, Avelino. "Strong organic bases as building blocks of mesoporous hybrid catalysts for C-C forming bond reactions". . p. 5175 - 5185. Retrieved 2013/01/15.