3-(Benzyloxymethyl)cyclopent-2-enone

Base Information

• Chemical Name: 3-(Benzyloxymethyl)cyclopent-2-enone
• CAS No.: 119090-37-8
• Molecular Formula: C₁₃H₁₄O₂
• Molecular Weight: 202.253
• DSSTox Substance ID: DTXSID001252018
• Mol file: 119090-37-8.mol

Synonyms:SCHEMBL4866570;GYKKMHLSOZPEPT-UHFFFAOYSA-N;DTXSID001252018;3-(benzyloxymethyl)cyclopent-2-enone;3-[(Phenylmethoxy)methyl]-2-cyclopenten-1-one;119090-37-8

Chemical Property of 3-(Benzyloxymethyl)cyclopent-2-enone

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 202.099379685
• Heavy Atom Count: 15
• Complexity: 249

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(=O)C=C1COCC2=CC=CC=C2

Technology Process of 3-(Benzyloxymethyl)cyclopent-2-enone

There total 2 articles about 3-(Benzyloxymethyl)cyclopent-2-enone 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: 84.0%

3-methoxycyclopent-2-enone (4683-50-5) + (benzyloxymethyl)tributylstannane (66222-28-4) → 3-<(benzyloxy)methyl>-2-cyclopentene-1-one (119090-37-8)

Guidance literature:

(benzyloxymethyl)tributylstannane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

3-methoxycyclopent-2-enone; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5.16667h; Inert atmosphere;

DOI:10.1002/chem.200802568

Reference yield:

3-ethoxycyclopent-2-en-1-one (22627-70-9) + (benzyloxymethyl)tributylstannane (66222-28-4) → 3-<(benzyloxy)methyl>-2-cyclopentene-1-one (119090-37-8)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1) THF, hexane, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min;

DOI:10.1021/jo00297a024

Reference yield: 86.0%

3-<(benzyloxy)methyl>-2-cyclopentene-1-one (119090-37-8) → 2-bromo-3-<(benzyloxy)methyl>-2-cyclopentene-1-one (119090-39-0)

Guidance literature:

With pyridine; pyridinium hydrobromide perbromide; In dichloromethane; at 3 ℃; for 14h;

DOI:10.1021/jo00297a024

upstream raw materials:

3-ethoxycyclopent-2-en-1-one

(benzyloxymethyl)tributylstannane

3-methoxycyclopent-2-enone

Downstream raw materials:

2-bromo-3-<(benzyloxy)methyl>-2-cyclopentene-1-one

3-Benzyloxymethyl-2-bromo-cyclopent-2-enol

1-<(benzyloxy)methyl>-2-bromo-3-(methoxymethoxy)-1-cyclopentene

{2-[(1R,2R)-2-((1R,2R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentylmethyl)-2-methyl-cyclopentyl]-ethoxy}-tert-butyl-dimethyl-silane