2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2Z)-

Base Information

• Chemical Name: 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2Z)-
• CAS No.: 189368-12-5
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Mol file: 189368-12-5.mol

Synonyms:

Chemical Property of 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2Z)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2Z)-

There total 9 articles about 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2Z)- 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: 99.0%

ethyl (Z)-3-iodopropenoate (31930-36-6) + phenylacetylene (536-74-3) → (Z)-5-phenyl 2-penten-4-ynoic acid ethyl ester (189368-12-5)

Guidance literature:

With potassium carbonate; (triphenylphosphine)(2,2'-bipyridine)copper(I) bromide; In toluene; at 110 ℃; for 8h;

DOI:10.1021/ol049706e DOI:10.1055/s-2005-869893

Reference yield: 79.0%

3-Phenyl-2-propyn-1-ol (1504-58-1) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester (117552-48-4) + (Z)-5-phenyl 2-penten-4-ynoic acid ethyl ester (189368-12-5)

Guidance literature:

With hollandite; In toluene; at 110 ℃; for 4h; diastereoselective reaction; Catalytic behavior;

DOI:10.1002/cctc.201300942

Reference yield: 46.0%

Phenylpropargyl aldehyde (2579-22-8) + ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate (188945-44-0) → (Z)-5-phenyl 2-penten-4-ynoic acid ethyl ester (189368-12-5)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In tetrahydrofuran; methanol; at -78 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.phytochem.2020.112287

upstream raw materials:

ethyl (Z)-3-iodopropenoate

phenylacetylene

3-Phenyl-2-propyn-1-ol

ethyl (triphenylphosphoranylidene)acetate

Downstream raw materials:

5-bromo-6-phenyl-2H-pyran-2-one

Refernces

• 1、 Gandhi, Soniya,Baire, Beeraiah. "Fe(III)-Catalyzed, Cyclizative Coupling between 2-Alkynylbenzoates and Carbinols: Rapid Generation of Polycyclic Isocoumarins and Phthalides and Mechanistic Study". supporting information. p. 2651 - 2657. Retrieved 2020/05/25.
• 2、 Kandasamy, Mohanraj,Huang, Yu- Hsuan,Ganesan, Balaji,Senadi, Gopal Chandru,Lin, Wei-Yu. "In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor". . p. 4349 - 4356. Retrieved 2019/07/03.