Ethyl 6-oxooct-7-enoate

Base Information

• Chemical Name: Ethyl 6-oxooct-7-enoate
• CAS No.: 50628-92-7
• Molecular Formula: C₁₀H₁₆O₃
• Molecular Weight: 184.235
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID70390804
• Wikidata: Q82187847
• Mol file: 50628-92-7.mol

Synonyms:Ethyl 6-oxooct-7-enoate;50628-92-7;ETHYL 6-KETO-7-OCTENOATE;DTXSID70390804;6-oxo-oct-7-enoic acid ethyl ester;AKOS006279965;(4-CHLORO-PHENYL)-PHOSPHONICACIDDIETHYLESTER

Chemical Property of Ethyl 6-oxooct-7-enoate

Chemical Property:

• Vapor Pressure: 0.0179mmHg at 25°C
• Refractive Index: 1.44
• Boiling Point: 253.8°C at 760 mmHg
• Flash Point: 104.7°C
• PSA: 43.37000
• Density: 0.973g/cm³
• LogP: 1.86500
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 185

Purity/Quality:

97% ^*data from raw suppliers

ETHYL-6-KETO-7-OCTENOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CCCCC(=O)C=C

Technology Process of Ethyl 6-oxooct-7-enoate

There total 4 articles about Ethyl 6-oxooct-7-enoate 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: 44.0%

ethyl 5-iodopentanoate (41302-32-3) + acryloyl chloride (814-68-6,25189-84-8) → ethyl 6-oxo-7-octenoate (50628-92-7)

Guidance literature:

ethyl 5-iodopentanoate; With zinc/copper couple; In N,N-dimethyl acetamide; toluene; at 20 - 80 ℃; for 16h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl acetamide; toluene; at 60 ℃; for 0.0833333h; Inert atmosphere;

acryloyl chloride; In N,N-dimethyl acetamide; toluene; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201403537

Reference yield:

ethyl 6-chloro-6-oxohexanoate (1071-71-2) → ethyl 6-oxo-7-octenoate (50628-92-7)

Guidance literature:

DOI:10.1021/ja01636a028 DOI:10.1021/ja01565a059 DOI:10.1021/ja01645a016 DOI:10.1021/ja01607a057

Reference yield:

ethyl 5-bromovalerate (14660-52-7) → ethyl 6-oxo-7-octenoate (50628-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium iodide / acetone / 14 h / Reflux; Inert atmosphere

2.1: zinc/copper couple / toluene; N,N-dimethyl acetamide / 16 h / 20 - 80 °C / Inert atmosphere

2.2: 0.08 h / 60 °C / Inert atmosphere

2.3: 4 h / 20 °C / Inert atmosphere

With zinc/copper couple; sodium iodide; In N,N-dimethyl acetamide; acetone; toluene;

DOI:10.1002/anie.201403537

upstream raw materials:

ethyl 6-chloro-6-oxohexanoate

ethene

ethyl 5-bromovalerate

ethyl 5-iodopentanoate

Downstream raw materials:

8-benzylsulfanyl-6-oxo-octanoic acid ethyl ester

8-benzylsulfanyl-6-oxo-octanoic acid

chlamydocin

(5S,11R,13aR)-5-Benzyl-11-{5-[2-(2-chloro-ethyl)-[1,3]dioxolan-2-yl]-pentyl}-8,8-dimethyl-decahydro-3a,6,9,12-tetraaza-cyclopentacyclododecene-4,7,10,13-tetraone