2-Cyclopenten-1-one, 2-[(S)-(4-methylphenyl)sulfinyl]-

Base Information

• Chemical Name: 2-Cyclopenten-1-one, 2-[(S)-(4-methylphenyl)sulfinyl]-
• CAS No.: 79681-26-8
• Molecular Formula: C12H12O2S
• Molecular Weight: 220.292
• DSSTox Substance ID: DTXSID20451313
• Wikidata: Q82271279
• Mol file: 79681-26-8.mol

Synonyms:79681-26-8;2-Cyclopenten-1-one, 2-[(S)-(4-methylphenyl)sulfinyl]-;DTXSID20451313

Chemical Property of 2-Cyclopenten-1-one, 2-[(S)-(4-methylphenyl)sulfinyl]-

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 220.05580079
• Heavy Atom Count: 15
• Complexity: 312

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)C2=CCCC2=O
• Isomeric SMILES: CC1=CC=C(C=C1)[S@](=O)C2=CCCC2=O

Technology Process of 2-Cyclopenten-1-one, 2-[(S)-(4-methylphenyl)sulfinyl]-

There total 5 articles about 2-Cyclopenten-1-one, 2-[(S)-(4-methylphenyl)sulfinyl]- 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: 90.0%

(S)-(+)-2-(p-toluenesulfinyl)-2-cyclopentenone ethylene ketal (82136-15-0) → 2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one (79681-26-8)

Guidance literature:

With copper(II) sulfate; In acetone;

DOI:10.1021/ja00379a022

Reference yield:

6-(Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene (82136-15-0) → 2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one (79681-26-8)

Guidance literature:

With copper(I) sulfate; copper(II) sulfate; In acetone; Ambient temperature;

DOI:10.1021/ja00400a076

Reference yield:

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1) → 2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one (79681-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / n-BuLi / tetrahydrofuran / 1.) -78 deg C, 90 min, 2.) -78 deg C, 15 min

2: 90 percent / cupric sulfate / acetone

With n-butyllithium; copper(II) sulfate; In tetrahydrofuran; acetone;

DOI:10.1021/ja00379a022

upstream raw materials:

6-(Toluene-4-sulfinyl)-1,4-dioxa-spiro[4.4]non-6-ene

(S)-(+)-2-(p-toluenesulfinyl)-2-cyclopentenone ethylene ketal

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene

(-)-menthyl p-toluenesulfinate

Downstream raw materials:

(R)-(+)-3-methylcyclopentanone 2,4-dinitrophenylhydrazone

methyl (-)-(1S,3S,3aR,6aS,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate

methyl (-)-(1R,3R,3aS,6aR,S_S)-4-oxo-3-phenyl-3a-p-tolylsulfinyloctahydrocyclopenta[c]pyrrole-1-carboxylate

(3aS,6aS,S_S)-6a-[(4-methylphenyl)sulfinyl]-3a,4,5,6a-tetrahydrocyclopenta[c]pyrazol-6(3H)-one