2,3-Dimethyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Base Information

• Chemical Name: 2,3-Dimethyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one
• CAS No.: 466634-65-1
• Molecular Formula: C10H14O
• Molecular Weight: 150.21756
• DSSTox Substance ID: DTXSID10479960
• Nikkaji Number: J1.730.234E
• Mol file: 466634-65-1.mol

Synonyms:466634-65-1;2,3-Dimethyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one;DTXSID10479960

Chemical Property of 2,3-Dimethyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Chemical Property:

• PSA: 17.07000
• LogP: 2.48790
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 223

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C(C1)CC=C)C

Technology Process of 2,3-Dimethyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

There total 4 articles about 2,3-Dimethyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one 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: 83.0%

2,3-dimethylcyclopent-2-enone (1121-05-7) + allyl bromide (106-95-6) → 5-allyl-2,3-dimethyl-cyclopent-2-enone (466634-65-1)

Guidance literature:

With manganese triacetate; In benzene; for 10h; Heating;

DOI:10.1016/S0040-4039(02)00726-8 DOI:10.1016/j.tet.2005.06.031

Reference yield: 68.0%

methyl 1-allyl-3,4-dimethyl-2-oxocyclopent-3-ene-1-carboxylate → 5-allyl-2,3-dimethyl-cyclopent-2-enone (466634-65-1)

Guidance literature:

With potassium tert-butylate; In methanol; at 80 ℃; for 3h; Schlenk technique;

DOI:10.1021/acs.orglett.1c01569

Reference yield:

2-methylbut-2-enoic acid (13201-46-2) → 5-allyl-2,3-dimethyl-cyclopent-2-enone (466634-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; sodium carbonate / 1,2-dichloro-ethane / 3 h / 130 °C / Schlenk technique

2: sodium carbonate / methanol / 3 h / 40 °C / Schlenk technique

3: potassium tert-butylate / methanol / 3 h / 80 °C / Schlenk technique

With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium tert-butylate; sodium carbonate; In methanol; 1,2-dichloro-ethane;

DOI:10.1021/acs.orglett.1c01569

upstream raw materials:

2,3-dimethylcyclopent-2-enone

allyl bromide

2-methylbut-2-enoic acid