(5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone

Base Information

Chemical Name:(5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone
CAS No.:6617-37-4
Molecular Formula:C15H12O3
Molecular Weight:240.25
Hs Code.:
Mol file:6617-37-4.mol

Synonyms:5-[(E)-5-Furan-3-yl-2-methyl-pent-2-en-4-yn-(Z)-ylidene]-3-methyl-5H-furan-2-one;freelingyne;Freelingyn;

Suppliers and Price of (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
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Total 3 raw suppliers

Chemical Property of (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone

Chemical Property:

PSA：39.44000
LogP:2.96440

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

General Description (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone, also known as freelingyne, is a γ-alkylidenebutenolide compound synthesized through a palladium-catalyzed stereocontrolled reaction. The synthesis involves Pd(0)-mediated coupling of vinyl halides with acetylene derivatives, followed by Pd(II)-catalyzed intramolecular cyclization to achieve the stereoselective formation of the (Z)-alkylidenebutenolide core. This method provides efficient access to the structurally complex molecule with defined stereochemistry.

Technology Process of (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone

There total 22 articles about (5Z)-5-[(E)-2-Methyl-5-(3-furyl)-2-pentene-4-ynylidene]-3-methyl-2(5H)-furanone 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: 66.0%

: 193478-03-4
(2Z,6E)-9-Furan-3-yl-2,6-dimethyl-nona-2,6-diene-4,8-diynoic acid

: 6617-37-4
5Z-5-[E-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ylidene]-3-methyl-2(5H)-furanone

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); triethylamine; 1,2-bis-(diphenylphosphino)ethane; In benzene; at 40 ℃; for 2h;
DOI:10.1016/S0040-4039(97)01187-8

Reference yield: 50.0%

: 162795-69-9
(Z)-3-iodo-2-methylpropenoic acid

: 193478-01-2
(E)-6-(3-furanyl)-3-methyl-3-hexene-1,5-diyne

: 6617-37-4
5Z-5-[E-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ylidene]-3-methyl-2(5H)-furanone

: (3E,8E)-1,11-bis(3-furanyl)-4,8-dimethyl-3,8-dodecadiene-1,5,7,10-tetrayne

Guidance literature:: With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 23 ℃; for 23h;
DOI:10.1021/jo971360g

Reference yield:

: 53768-16-4
(E)-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ol

: 6617-37-4
5Z-5-[E-5-(3-furanyl)-2-methyl-2-penten-4-yn-1-ylidene]-3-methyl-2(5H)-furanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 - 23 °C

2.1: Ph₃P; K₂CO₃ / CH₂Cl₂ / 0.5 h / 23 °C

2.2: 95 percent / CH₂Cl₂ / 0.33 h

3.1: NaN(SiMe₃)2 / tetrahydrofuran / 0.17 h / -100 °C

3.2: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -100 °C

3.3: 91 percent / MeOH / tetrahydrofuran; hexane / -100 °C

4.1: 50 percent / NEt₃ / Pd(PPh₃)4; CuI / acetonitrile / 23 h / 23 °C

With sodium hexamethyldisilazane; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile; 1.1: Oxidation / 2.1: Corey-Fuchs olefination / 2.2: Corey-Fuchs olefination / 3.1: Dehydrobromination / 3.2: Metallation / 3.3: Hydrolysis / 4.1: Dimerization;
DOI:10.1021/jo971360g