(2E,4E)-5-Phenyl-penta-2,4-dienoicacidethylester

Base Information

• Chemical Name: (2E,4E)-5-Phenyl-penta-2,4-dienoicacidethylester
• CAS No.: 39806-16-1
• Molecular Formula: C13H14 O2
• Molecular Weight: 202.253
• DSSTox Substance ID: DTXSID90699422
• Mol file: 39806-16-1.mol

Synonyms:SCHEMBL3685507;DTXSID90699422;(2E,4E)-5-PHENYL-PENTA-2,4-DIENOICACIDETHYLESTER

Chemical Property of (2E,4E)-5-Phenyl-penta-2,4-dienoicacidethylester

Chemical Property:

• Boiling Point: 135-136 °C(Press: 3 Torr)
• PSA: 26.30000
• Density: 1.045±0.06 g/cm3(Predicted)
• LogP: 2.81910
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 202.099379685
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

99%min ^*data from raw suppliers

(2E,4E)-5-PHENYL-PENTA-2,4-DIENOIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (2E,4E)-5-Phenyl-penta-2,4-dienoicacidethylester

There total 91 articles about (2E,4E)-5-Phenyl-penta-2,4-dienoicacidethylester 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: 98.0%

(E)-3-phenylpropenal (14371-10-9) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate (39806-16-1)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

(E)-3-phenylpropenal; In tetrahydrofuran; mineral oil; at 0 - 22 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.8b10885

Reference yield: 97.0%

diazoacetic acid ethyl ester (623-73-4) + 3-phenyl-propenal (104-55-2) → (2E)-ethyl 5-phenylpenta-2,4-dienoate (38447-06-2,38448-85-0,39806-16-1,136265-12-8,1552-95-0,106925-11-5)

Guidance literature:

With tributylstibine; copper(l) iodide; In benzene; at 50 ℃; for 4h;

DOI:10.1016/S0040-4039(00)97988-7

Reference yield: 96.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-phenyl-propenal (104-55-2) → (2E)-ethyl 5-phenylpenta-2,4-dienoate (38447-06-2,38448-85-0,39806-16-1,136265-12-8,1552-95-0,106925-11-5) + Cinnamic acid (621-82-9)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; 3-phenyl-propenal; With potassium carbonate; for 6h; Neat (no solvent); high-speed ball milling;

With Oxone; for 12h; optical yield given as %de; diastereoselective reaction; Neat (no solvent); high-speed ball milling;

DOI:10.1039/c0gc00671h

upstream raw materials:

ethyl (2E)-4-(diethoxyphosphoryl)crotonate

benzaldehyde

diazoacetic acid ethyl ester

3-phenyl-propenal

Downstream raw materials:

ethyl (E)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate

5-phenylpenta-2,4-dienoic acid

ethyl 2-hydroxymethyl-2,3,5,8-tetrahydro-1,3-dioxo-8-phenyl-1H-1,2,4-triazolo[1,2-a]pyridazine-5-carboxylate

C₁₃H₁₆O₄

Refernces

• 1、 Bezerra Fran?a, Saraliny,Carine Barros de Lima, Luana,Rychard da Silva Cunha, Cristhyan,Santos Anuncia??o, Daniela,Ferreira da Silva-Júnior, Edeildo,Ester de Sá Barreto Barros, Maria,José da Paz Lima, Dimas. "Larvicidal activity and in silico studies of cinnamic acid derivatives against Aedes aegypti (Diptera: Culicidae)". . . Retrieved 2021/07/07.
• 2、 Banerjee, Prabal,Kaur, Navpreet,Singh, Priyanka. "Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones". . p. 3393 - 3406. Retrieved 2020/03/23.