Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate

Base Information

• Chemical Name: Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate
• CAS No.: 67695-10-7
• Molecular Formula: C10H14O3
• Molecular Weight: 182.219
• DSSTox Substance ID: DTXSID70557192
• Mol file: 67695-10-7.mol

Synonyms:67695-10-7;Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate;SCHEMBL927182;DTXSID70557192;STGUGVFKWOHXTH-UHFFFAOYSA-N;2-Carboethoxy-3-vinylcyclopentanone;Ethyl 2-oxo-5-vinylcyclopentanecarboxylate

Chemical Property of Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 232

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: CCOC(=O)C1C(CCC1=O)C=C

Technology Process of Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate

There total 1 articles about Ethyl 2-ethenyl-5-oxocyclopentane-1-carboxylate 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: 9.5%

ethyl (E)-2-chloro-3-oxo-6-octenoate (113704-19-1) → ethyl 2-hydroxy-6-methylbenzoate (6555-40-4) + ethyl 2-ethenyl-5-oxocyclopentanecarboxylate (67695-10-7) + (1R,5S)-1-Chloro-2-oxo-5-vinyl-cyclopentanecarboxylic acid ethyl ester (113704-22-6)

Guidance literature:

With copper diacetate; manganese triacetate; acetic acid; zinc; Yield given. Multistep reaction; 1.) RT, 36 h, glacial acetic acid, 2.) 25 deg C, 5 h;

DOI:10.1021/jo00245a001

Reference yield:

ethyl 2-ethenyl-5-oxocyclopentanecarboxylate (67695-10-7) → C30H40ClN5O3

Guidance literature:

Multi-step reaction with 6 steps

1: ammonium acetate / methanol

2: ammonium formate / 24 h / 150 °C

3: trichlorophosphate / 1,2-dichloro-ethane / 6 h / Reflux

4: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux; Inert atmosphere

5: hydrogenchloride / dichloromethane; 1,4-dioxane / 12 h

6: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / 4 h / 0 - 20 °C

With hydrogenchloride; ammonium acetate; ammonium formate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; butan-1-ol;

DOI:10.1021/jm301024w

Reference yield:

ethyl 2-ethenyl-5-oxocyclopentanecarboxylate (67695-10-7) → C29H40ClN5O4 (1001180-93-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ammonium acetate / methanol

2.1: ammonium formate / 24 h / 150 °C

3.1: trichlorophosphate / 1,2-dichloro-ethane / 6 h / Reflux

4.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux; Inert atmosphere

5.1: ozone / dichloromethane / 0.25 h / -78 °C

5.2: 1 h / 20 °C

5.3: 20 h / 0 °C

6.1: Resolution of racemate

7.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 12 h

8.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / 4 h / 0 - 20 °C

With hydrogenchloride; ammonium acetate; ammonium formate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; ozone; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; butan-1-ol;

DOI:10.1021/jm301024w

upstream raw materials:

ethyl (E)-2-chloro-3-oxo-6-octenoate

Downstream raw materials:

C₂₉H₄₀ClN₅O₄

C₂₄H₃₁ClFN₅O