ETHYL (E)-2-ACETYL-5-PHENYL-4-PENTENOATE

Base Information

• Chemical Name: ETHYL (E)-2-ACETYL-5-PHENYL-4-PENTENOATE
• CAS No.: 108400-97-1
• Molecular Formula: C15H18O3
• Molecular Weight: 246.306
• Mol file: 108400-97-1.mol

Synonyms:4-(Ethoxycarbonyl)-1-phenyl-1-hexen-5-one;(E)-ethyl 2-acetyl-5-phenylpent-4-enoate;ethyl (4E)-2-acetyl-5-phenylpent-4-enoate;ETHYL-(E)-2-ACETYL-5-PHENYL-4-PENTENOATE;ethyl 2-acetyl-5-phenyl-4-pentenoate;acetyl-2 phenyl-5 pentene-4 oate d'ethyle;acetyl-2 phenyl-5 pentene-4 oate d'ethyle (E);

Chemical Property of ETHYL (E)-2-ACETYL-5-PHENYL-4-PENTENOATE

Chemical Property:

• Boiling Point: 391.4±42.0 °C(Predicted)
• PKA: 11.44±0.59(Predicted)
• PSA: 43.37000
• Density: 1.068±0.06 g/cm3(Predicted)
• LogP: 2.85820

Purity/Quality:

ETHYL-(E)-2-ACETYL-5-PHENYL-4-PENTENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ETHYL (E)-2-ACETYL-5-PHENYL-4-PENTENOATE

There total 29 articles about ETHYL (E)-2-ACETYL-5-PHENYL-4-PENTENOATE 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: 93.0%

Cinnamyl acetate (21040-45-9) + ethyl acetoacetate (141-97-9) → ethyl (4E)-2-acetyl-5-phenylpent-4-enoate (108400-97-1,69916-33-2)

Guidance literature:

With trisodium tris(3-sulfophenyl)phosphine; 1-ethyl-3-methylimidazolium tetrafluoroborate; triethylamine; palladium diacetate; In water; for 0.05h; microwave irradiation;

DOI:10.1016/j.tetlet.2005.04.002

Reference yield: 89.0%

cinnamyl acetate (103-54-8) + ethyl acetoacetate (141-97-9) → ethyl (4E)-2-acetyl-5-phenylpent-4-enoate (108400-97-1,69916-33-2)

Guidance literature:

With Pd(?-C3H5)<(Ph2PC6H4CONH)2Tenta Gel S>; potassium carbonate; In water; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(97)00702-8

Reference yield: 88.0%

ethyl acetoacetate (141-97-9) → ethyl (4E)-2-acetyl-5-phenylpent-4-enoate (108400-97-1,69916-33-2)

Guidance literature:

ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

cinnamyl halide; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol501010k

upstream raw materials:

trans-3-phenylprop-2-enyl chloride

sodium ethyl acetylacetate enolate

Cinnamyl bromide

ethyl 2-acetyl-3-phenyl-4-pentenoate

Downstream raw materials:

ethyl (4E)-2-acetyl-2-benzoylmethyl-5-phenylpent-4-enoate

1t-phenyl-hexen-⁽¹⁾-one-⁽⁵⁾-semicarbazone

(E)-6-Phenyl-5-hexen-2-one oxime

(4E)-2-diazo-5-phenyl-4-pentenoic acid ethyl ester

Refernces

• 1、 Danjo, Hiroshi,Tanaka, Daiki,Hayashi, Tamio,Uozumi, Yasuhiro. "Allylic substitution in water catalyzed by amphiphilic resin-supported palladium-phosphine complexes". . p. 14341 - 14352. Retrieved 1999.
• 2、 Stefani, Hélio A.,Costa, Iguatemi M.,De O. Silva, Diogo,Menezes, Paulo H.,Rodrigues, Alessandro. "Selenocyclofunctionalization of β-ketoamides: Synthesis of substituted dihydrofurans". . p. 141 - 152. Retrieved 2001.
• 3、 Kling, Robert,Sinou, Denis,Pozzi, Gianluca,Choplin, Agnes,Quignard, Francoise,Busch, Stefan,Kainz, Sabine,Koch, Daniel,Leitner, Walter. "Palladium(0)-catalyzed substitution of allylic substrates in perfluorinated solvents". . p. 9439 - 9442. Retrieved 1998.
• 4、 Uozumi, Yasuhiro,Danjo, Hiroshi,Hayashi, Tamio. "New amphiphilic palladium-phosphine complexes bound to solid supports: Preparation and use for catalytic allylic substitution in aqueous media". . p. 3557 - 3560. Retrieved 1997.
• 5、 Barik, Rasmita,Halder, Joydev,Nanda, Samik. "Biocatalytic dynamic kinetic reductive resolution with ketoreductase from: Klebsiella pneumoniae: The asymmetric synthesis of functionalized tetrahydropyrans". . p. 8571 - 8588. Retrieved 2019/10/02.