2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-

Base Information

• Chemical Name: 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-
• CAS No.: 774-64-1
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.247
• DSSTox Substance ID: DTXSID901009987
• Nikkaji Number: J13.155E,J665.471A
• Mol file: 774-64-1.mol

Synonyms:774-64-1;2(5H)-Furanone,3,4-dimethyl-5-pentylidene-, (5Z)-;2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-;Bovolid;2,4-Nonadienoic acid, 4-hydroxy-2,3-dimethyl-, .gamma.-lactone;4-HYDROXY-2,3-DIMETHYL-2,4-NONADIENOIC ACID GAMMA LACTONE;DTXSID901009987;3,4-Dimethyl-5-[(Z)-pentylidene]furan-2(5H)-one

Chemical Property of 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-

Chemical Property:

• Vapor Pressure: 0.00192mmHg at 25°C
• Refractive Index: 1.4708 (estimate)
• Boiling Point: 291.7°C at 760 mmHg
• Flash Point: 118.1°C
• PSA: 26.30000
• Density: 1.046g/cm³
• LogP: 2.60610
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 180.115029749
• Heavy Atom Count: 13
• Complexity: 272

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=C1C(=C(C(=O)O1)C)C
• Isomeric SMILES: CCCC/C=C\1/C(=C(C(=O)O1)C)C

Technology Process of 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)-

There total 16 articles about 2(5H)-Furanone, 3,4-dimethyl-5-pentylidene-, (5Z)- 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: 92.0%

C11H16O2 → (Z)-3,4-dimethyl-5-pentylidenefuran-2(5H)-one (774-64-1)

Guidance literature:

With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 6h; Reflux;

DOI:10.1016/j.tetlet.2011.11.001

Reference yield: 85.0%

(Z)-3-iodo-4-methyl-5-pentylidenefuran-2(5H)-one (1360895-25-5) + zinc methyl bromide (18815-74-2) → (Z)-3,4-dimethyl-5-pentylidenefuran-2(5H)-one (774-64-1)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In diethyl ether; N,N-dimethyl-formamide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201102570

Reference yield: 74.0%

(Z)-3-(bromomethyl)-4-methyl-5-pentylidenefuran-2(5H)-one → (Z)-3,4-dimethyl-5-pentylidenefuran-2(5H)-one (774-64-1)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02151

upstream raw materials:

carbon monoxide

tetramethylstannane

3-Bromo-4-methyl-5-pent-(Z)-ylidene-5H-furan-2-one

dimethylacetylene

Refernces

• 1、 Park, Bo Ram,Kim, Ko Hoon,Lim, Jin Woo,Kim, Jae Nyoung. "Facile synthesis of γ-alkylidenebutenolides from Morita-Baylis- Hillman adducts". . p. 36 - 40. Retrieved 2012/01/05.
• 2、 Benneche, Tore,Hussain, Zainab,Aamdal Scheie, Anne,Loenn-Stensrud, Jessica. "Synthesis of 5-(bromomethylene)furan-2(5H)-ones and 3-(bromomethylene) isobenzofuran-1(3H)-ones as inhibitors of microbial quorum sensing". experimental part. p. 1567 - 1572. Retrieved 2009/04/10.