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

Base Information

• Chemical Name: 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2E)-
• CAS No.: 117552-48-4
• Molecular Formula: C13H12O2
• Molecular Weight: 200.237
• Mol file: 117552-48-4.mol

Synonyms:

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

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, (2E)-

There total 21 articles about 2-Penten-4-ynoic acid, 5-phenyl-, ethyl ester, (2E)- 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 (E)-3-iodopropenoate (31930-36-6,31930-37-7) + phenylacetylene (536-74-3) → E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester (117552-48-4)

Guidance literature:

With caesium carbonate; (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; In toluene; at 110 ℃; for 24h;

DOI:10.1021/ol049706e

Reference yield: 79.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + phenylpropynoic acid methyl ester (4891-38-7) → E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester (117552-48-4)

Guidance literature:

phenylpropynoic acid methyl ester; With {μ-ClIr(cyclooctene)2}2; H₂SiEt₂; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere;

diethoxyphosphoryl-acetic acid ethyl ester; With potassium trimethylsilonate; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/acs.orglett.5b02901

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

upstream raw materials:

Phenylpropargyl aldehyde

diethoxyphosphoryl-acetic acid ethyl ester

ethyl (E)-3-iodopropenoate

phenylacetylene

Downstream raw materials:

ethyl (E)-3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloylate

(E)-(5-chloropent-3-en-1-yn-1-yl)benzene

(E)-(S)-2-ethoxy-3-[4-(5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester

(E)-5-phenyl-pent-2-en-4-ynoic acid

Refernces

• 1、 Fairlamb, Ian J. S.,Lee, Adam F.,Loe-Mie, Faidjiba E. M.,Niemel?, Elina H.,O'Brien, Ciara T.,Whitwood, Adrian C.. "Halogenated-2-pyrones in Sonogashira cross-coupling: limitations, optimisation and consequences for GC analysis of Pd-mediated reactions". . p. 9827 - 9838. Retrieved 2005.
• 2、 Ren, Cheng,Shi, Zhenyu,Ding, Weijie,Liu, Zhiqing,Jin, Huile,Yu, Xiaochun,Wang, Shun. "Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction". supporting information. p. 14 - 17. Retrieved 2017/12/06.
• 3、 Jarava-Barrera, Carlos,Parra, Alejandro,Amenós, Laura,Arroyo, Ana,Tortosa, Mariola. "Stereoselective Traceless Borylation–Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst". supporting information. p. 17478 - 17481. Retrieved 2017/11/30.