ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate

Base Information

• Chemical Name: ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate
• CAS No.: 72568-47-9
• Molecular Formula: C16H16 N2 O3
• Molecular Weight: 284.315
• DSSTox Substance ID: DTXSID30381511
• Nikkaji Number: J599.803D
• ChEMBL ID: CHEMBL1087042
• Mol file: 72568-47-9.mol

Synonyms:ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate;72568-47-9;4H-Pyran-3-carboxylicacid, 6-amino-5-cyano-2-methyl-4-phenyl-, ethyl ester;ChemDiv1_001154;Oprea1_359158;Oprea1_702052;MLS000712348;CHEMBL1087042;HMS590E10;DTXSID30381511;HMS2679E20;CCG-15825;STK073894;AKOS000487264;AKOS016043076;SMR000282115;CS-0319499;FT-0626142;AB00591623-02;AF-886/30811002;SR-01000410022;SR-01000410022-1;F1524-0285;2-Amino-3-cyano-4-phenyl-5-carbethoxy-6-methyl-4H-pyran;2-Amino-3-cyano-4-phenyl-5-carboethoxy-6-methyl-4H-pyran

Chemical Property of ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate

Chemical Property:

• Vapor Pressure: 5.04E-10mmHg at 25°C
• Melting Point: 189℃
• Boiling Point: 497.2°C at 760 mmHg
• Flash Point: 254.5°C
• PSA: 85.34000
• Density: 1.24g/cm³
• LogP: 3.03168
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 284.11609238
• Heavy Atom Count: 21
• Complexity: 533

Purity/Quality:

98%min ^*data from raw suppliers

ethyl6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S36/37:Wear suitable protective clothing and gloves.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(OC(=C(C1C2=CC=CC=C2)C#N)N)C

Technology Process of ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate

There total 13 articles about ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate 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: 100.0%

ethyl acetoacetate (141-97-9) + benzaldehyde (100-52-7) + malononitrile (109-77-3) → 2-amino-3-cyano-5-ethoxycarbonyl-6-methyl-4-phenyl-4H-pyran (72568-47-9)

Guidance literature:

With 6C₄H₁₂N⁽¹⁺⁾*6H₂O*Nb₁₀O₂₈^(6-); In neat (no solvent); at 80 ℃; for 1h; Microwave irradiation;

DOI:10.1007/s11164-018-3440-y

Reference yield: 97.0%

Benzylidenemalononitrile (2700-22-3) + ethyl acetoacetate (141-97-9) → 2-amino-3-cyano-5-ethoxycarbonyl-6-methyl-4-phenyl-4H-pyran (72568-47-9)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In water; at 100 ℃; for 12h;

Reference yield: 87.0%

(Z)-ethyl 2-benzylidenacetoacetate (15802-62-7,15802-63-8,620-80-4) + malononitrile (109-77-3) → 2-amino-3-cyano-5-ethoxycarbonyl-6-methyl-4-phenyl-4H-pyran (72568-47-9)

Guidance literature:

With piperidine; In ethanol; Ambient temperature;

upstream raw materials:

Benzylidenemalononitrile

ethyl acetoacetate

ethyl benzylidenecyanoacetate

5-acetyl-2-amino-3-cyano-6-methyl-4-phenyl-4H-pyran

Downstream raw materials:

6-Amino-5-(1-amino-2,2-dicyano-vinyl)-2-methyl-4-phenyl-4H-pyran-3-carboxylic acid ethyl ester

ethyl 4-chloro-2-dimethylamino-7-methyl-5-phenyl-5H-pyrano<2,3-d>pyrimidin-6-carboxylate

Ethyl 2-butynoate

(E)-2-cyano-3-phenylacrylamide

Refernces

• 1、 Hajlaoui, Amel,Laajimi, Maha,Znati, Mansour,Jannet, Hichem Ben,Romdhane, Anis. "Novel pyrano-triazolo-pyrimidine derivatives as anti- α-amylase agents: Synthesis, molecular docking investigations and computational analysis". . . Retrieved 2021.
• 2、 Heravi, Majid M.,Beheshtiha, Yahya S.,Pirnia, Zahra,Sadjadi, Samaheh,Adibi, Mina. "One-pot, three-component synthesis of 4H-pyrans using cu(II) oxymetasilicate". . p. 3663 - 3667. Retrieved 2009.
• 3、 Dowarah, Jayanta,Lalhruaizela,Marak, Brilliant N.,Patel, Devanshi,Singh, Ved Prakash,Sran, Balkaran Singh,Yadav, Umesh Chand Singh. "Supramolecular architectures in dihydropyridones: Synthesis, crystal structure, Hirshfeld analysis, cytotoxicity and in silico studies". . . Retrieved 2021/10/19.
• 4、 Azimzadeh-Sadeghi, Setareh,Yavari, Issa. "Choline chloride/pentaerythritol: a deep eutectic solvent for the synthesis of pyran and chromene derivatives". . p. 1261 - 1267. Retrieved 2020/11/23.