2-Allyl-2-methyl-1,3-cyclopentanedione

Base Information

• Chemical Name: 2-Allyl-2-methyl-1,3-cyclopentanedione
• CAS No.: 26828-48-8
• Molecular Formula: C9H12O2
• Molecular Weight: 152.19
• Hs Code.: 2914299000
• European Community (EC) Number: 622-978-3
• NSC Number: 380474
• DSSTox Substance ID: DTXSID20181320
• Nikkaji Number: J236.292I
• Wikidata: Q83051928
• Mol file: 26828-48-8.mol

Synonyms:2-Allyl-2-methyl-1,3-cyclopentanedione;26828-48-8;2-methyl-2-prop-2-enylcyclopentane-1,3-dione;2-methyl-2-(prop-2-en-1-yl)cyclopentane-1,3-dione;NSC380474;2-allyl-2-methylcyclopentane-1,3-dione;SCHEMBL666966;DTXSID20181320;MCOMBKZMVPQQKK-UHFFFAOYSA-N;AKOS005137944;NSC 380474;NSC-380474;2-Allyl-2-methyl-cyclopentane-1,3-dione;2-Allyl-2-methyl-1,3-cyclopentanedione, 97%;1,3-cyclopentanedione, 2-methyl-2-(2-propenyl)-;J-507714;InChI=1/C9H12O2/c1-3-6-9(2)7(10)4-5-8(9)11/h3H,1,4-6H2,2H

Chemical Property of 2-Allyl-2-methyl-1,3-cyclopentanedione

Chemical Property:

• Vapor Pressure: 0.0736mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Boiling Point: 228.4 °C at 760 mmHg
• Flash Point: 95.6 °C
• PSA: 34.14000
• Density: 1.019 g/cm³
• LogP: 1.50080
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Allyl-2-methyl-1,3-cyclopentanedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(=O)CCC1=O)CC=C
• Uses: 2-Allyl-2-methyl-1,3-cyclopentanedione was used in the synthesis of copolymers containing pendant substituted 5-membered rings as side groups by undergoing copolymerization with ethylene.

Technology Process of 2-Allyl-2-methyl-1,3-cyclopentanedione

There total 10 articles about 2-Allyl-2-methyl-1,3-cyclopentanedione 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%

2-Methylcyclopentane-1,3-dione (765-69-5) + allyl alcohol (107-18-6) → 2-allyl-2-methyl-1,3-cyclopentanedione (26828-48-8)

Guidance literature:

With Ru(Cp*)(η3-C3H5)(p-CH3C6H5SO3)2; In dichloromethane; acetonitrile; at 50 ℃; for 3h; regioselective reaction;

DOI:10.1002/adsc.200900568

Reference yield: 94.0%

2-Methylcyclopentane-1,3-dione (765-69-5) + Allyl acetate (591-87-7) → 2-allyl-2-methyl-1,3-cyclopentanedione (26828-48-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; Heating;

Reference yield: 91.0%

2-Methylcyclopentane-1,3-dione (765-69-5) + allyl bromide (106-95-6) → 2-allyl-2-methyl-1,3-cyclopentanedione (26828-48-8)

Guidance literature:

2-Methylcyclopentane-1,3-dione; With tetra-(n-butyl)ammonium iodide; sodium hydroxide; In water; at 0 - 20 ℃; for 0.166667h;

allyl bromide; In water; at 50 ℃; for 8h;

DOI:10.1021/acs.joc.8b03138

upstream raw materials:

2-Methylcyclopentane-1,3-dione

allyl bromide

Allyl acetate

3-Allyl-3-methyl-2,4-dioxo-cyclopentanecarboxylic acid ethyl ester

Downstream raw materials:

(+)-(2S,3S)-3-Hydroxy-2-methyl-2-(prop-2-enyl)-cyclopentanon

(2S,3R)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one

(2S,3S)-2-allyl-3-hydroxy-2-methylcyclopentan-1-one

Refernces

• 1、 Ao, Yu-Fei,Wang, De-Xian,Zhao, Liang,Wang, Mei-Xiang. "Synthesis of quaternary-carbon-containing and functionalized enantiopure pentanecarboxylic acids from biocatalytic desymmetrization of meso-cyclopentane-1,3-dicarboxamides". . p. 938 - 947. Retrieved 2015.
• 2、 Werner, Thomas,Hoffmann, Marcel,Deshmukh, Sunetra. "First Enantioselective Catalytic Wittig Reaction". . p. 6630 - 6633. Retrieved 2014.
• 3、 Kawamoto, Yuichiro,Noguchi, Naoki,Ozone, Daiki,Kobayashi, Toyoharu,Ito, Hisanaka. "Convenient preparation of synthetically useful chiral quaternary carbon-containing bicyclic compounds with organocatalysts". supporting information. . Retrieved 2021/11/01.
• 4、 Contente, Martina Letizia,Dall’Oglio, Federica,Annunziata, Francesca,Molinari, Francesco,Rabuffetti, Marco,Romano, Diego,Tamborini, Lucia,Rother, D?rte,Pinto, Andrea. "Stereoselective Reduction of Prochiral Cyclic 1,3-Diketones Using Different Biocatalysts". . p. 1176 - 1185. Retrieved 2019/11/16.