Ethyl 3-oxo-6-heptenoate

Base Information

• Chemical Name: Ethyl 3-oxo-6-heptenoate
• CAS No.: 17605-06-0
• Molecular Formula: C9H14O3
• Molecular Weight: 170.208
• Hs Code.: 2918300090
• European Community (EC) Number: 631-504-4
• NSC Number: 62677
• DSSTox Substance ID: DTXSID40289670
• Nikkaji Number: J24.747B
• Wikidata: Q82027085
• Mol file: 17605-06-0.mol

Synonyms:ethyl 3-oxohept-6-enoate;Ethyl 3-oxo-6-heptenoate;17605-06-0;6-Heptenoic acid, 3-oxo-, ethyl ester;3-Oxo-6-heptenoic acid ethyl;NSC62677;3-oxo-hept-6-enoic acid ethyl ester;ethyl allylacetoacetate;ethyl3-oxohept-6-enoate;SCHEMBL959397;allylacetoacetic acid ethyl ester;DTXSID40289670;MFCD00026910;NSC-62677;AKOS006343298;BS-16253;CS-0320795;D82674

Chemical Property of Ethyl 3-oxo-6-heptenoate

Chemical Property:

• Vapor Pressure: 0.0781mmHg at 25°C
• Refractive Index: 1.437
• Boiling Point: 227.3 °C at 760 mmHg
• Flash Point: 90.989 °C
• PSA: 43.37000
• Density: 0.985 g/cm³
• LogP: 1.47490
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 170.094294304
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99%, ^*data from raw suppliers

Ethyl3-Oxohept-6-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)CCC=C

Technology Process of Ethyl 3-oxo-6-heptenoate

There total 7 articles about Ethyl 3-oxo-6-heptenoate 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: 86.0%

ethyl acetoacetate (141-97-9) + allyl bromide (106-95-6) → ethyl 3-oxohept-6-enoate (17605-06-0)

Guidance literature:

ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.05.041

Reference yield: 76.0%

5-Hexen-2-one (109-49-9) + Diethyl carbonate (105-58-8,76619-83-5) → ethyl 3-oxohept-6-enoate (17605-06-0)

Guidance literature:

With sodium hydride;

DOI:10.1021/ja00379a037

Reference yield: 74.0%

pent-4-enoic acid (591-80-0) + ethyl acetate (141-78-6) → ethyl 3-oxohept-6-enoate (17605-06-0)

Guidance literature:

pent-4-enoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 1h;

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

ethyl acetate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3.75h;

DOI:10.1039/c2ob26641e

upstream raw materials:

5-Hexen-2-one

Diethyl carbonate

ethyl acetoacetate

allyl bromide

Downstream raw materials:

4-hydroxy-isophthalic acid-3-ethyl ester

Ethyl 3-oxoheptanoate

(E)-3-Phenylamino-hepta-2,6-dienoic acid ethyl ester

ethyl 2-methyl-3-oxo-hept-6-enoate

Refernces

• 1、 Kongkathip, Boonsong,Sookkho, Rongsan,Kongkathip, Ngampong,Taylor, Walter C.. "Syntheses of both diastereoisomers of 2,8-dioxabicyclo[3.2.1]octane derivatives: Degradation products of Daphniphyllum alkaloids". . p. 1095 - 1096. Retrieved 1999.
• 2、 Pinnick,Chang. "". . p. 837,839. Retrieved 1979.
• 3、 Furuta, Miyu,Ide, Kohta,Tokuyama, Hidetoshi. "Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters". supporting information. p. 9172 - 9176. Retrieved 2021/11/13.
• 4、 Inada, Haruki,Furukawa, Keisuke,Shibuya, Masatoshi,Yamamoto, Yoshihiko. "One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols". supporting information. p. 15105 - 15108. Retrieved 2019/12/26.