Methyl [(1S)-4-oxocyclopent-2-en-1-yl]acetate

Base Information

• Chemical Name: Methyl [(1S)-4-oxocyclopent-2-en-1-yl]acetate
• CAS No.: 84559-56-8
• Molecular Formula: C8H10O3
• Molecular Weight: 154.166
• DSSTox Substance ID: DTXSID50546403
• Wikidata: Q82424236
• Mol file: 84559-56-8.mol

Synonyms:Methyl [(1S)-4-oxocyclopent-2-en-1-yl]acetate;84559-56-8;SCHEMBL16614334;DTXSID50546403

Chemical Property of Methyl [(1S)-4-oxocyclopent-2-en-1-yl]acetate

Chemical Property:

• Boiling Point: 238.6±19.0 °C(Predicted)
• PSA: 43.37000
• Density: 1.132±0.06 g/cm3(Predicted)
• LogP: 0.69470
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 154.062994177
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC1CC(=O)C=C1
• Isomeric SMILES: COC(=O)C[C@@H]1CC(=O)C=C1

Technology Process of Methyl [(1S)-4-oxocyclopent-2-en-1-yl]acetate

There total 1 articles about Methyl [(1S)-4-oxocyclopent-2-en-1-yl]acetate 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:

(R)-4-acetoxycyclopent-2-en-1-one (59995-48-1) → (S)-methyl 2-(4-oxocyclopent-2-en-1-yl)acetate (84559-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃, 18-crown-6 / toluene / 18 h / 0 °C

2: decarboxylation

With 18-crown-6 ether; potassium carbonate; In toluene;

Reference yield:

(S)-methyl 2-(4-oxocyclopent-2-en-1-yl)acetate (84559-56-8) → (+)-brefeldin A (20350-15-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) CpZrHCl, 2.) Ni(acac)2, diisobutylaluminium hydride / 1.) THF, 0 deg C, 2.) THF, -10 deg C then 0 deg C, 8 h

2: 1.) Li-sec-Bu₃BH (L-Selectride), 2.) tosic acid / 1.) THF, -78 deg C, 2 h, 2.) toluene, reflux, 10 h

3: 97 percent / diisopropylethylamine / CH₂Cl₂ / 10 h / 23 °C

4: 98 percent / i-Bu₂AlH / CH₂Cl₂ / 1.5 h / -78 °C

5: 94 percent / piperidine / acetonitrile / 48 h / 5 °C

6: 90 percent / diisopropylethylamine / CH₂Cl₂ / 23 °C

7: 87 percent / HOAc, H₂O (3:1) / 5 h / 23 °C

8: 93 percent / 0.15 M LiOH / 24 h / 23 °C / MeOH, H₂O (6:1)

9: 1.) lactonization, 2.) MEM ether cleavage

With piperidine; bis(acetylacetonate)nickel(II); lithium hydroxide; CpZrHCl; water; L-Selectride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)97297-6

Reference yield:

(S)-methyl 2-(4-oxocyclopent-2-en-1-yl)acetate (84559-56-8) → C25H39NO5Si + C25H39NO5Si

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper(I) cyanide di(lithium chloride) / tetrahydrofuran / 0.25 h / -55 - -40 °C / Inert atmosphere

1.2: 0.17 h / -40 °C / Inert atmosphere

1.3: -40 - 20 °C / Inert atmosphere

2.1: bis(η3-allyl-μ-chloropalladium(II)); XPhos / diethylene glycol dimethyl ether / 2 h / 100 °C / Inert atmosphere

With bis(η3-allyl-μ-chloropalladium(II)); copper(I) cyanide di(lithium chloride); XPhos; In tetrahydrofuran; diethylene glycol dimethyl ether; 1.1: |Michael Addition / 1.2: |Michael Addition;

DOI:10.1002/anie.202005380

upstream raw materials:

(R)-4-acetoxycyclopent-2-en-1-one

Downstream raw materials:

(+)-brefeldin A

(1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene

(1R,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene

(4R)-4-{(2Z)-7-[(4-methoxybenzyl)oxy]hept-2-en-1-yl}cyclopent-2-en-1-one