3-Ethoxy-2-cyclohexen-1-one

Base Information

• Chemical Name: 3-Ethoxy-2-cyclohexen-1-one
• CAS No.: 5323-87-5
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Hs Code.: 29145000
• European Community (EC) Number: 226-190-7
• NSC Number: 2826
• UNII: DV46J47XJS
• DSSTox Substance ID: DTXSID30201326
• Nikkaji Number: J208.495C
• Wikidata: Q83074516
• Mol file: 5323-87-5.mol

Synonyms:3-Ethoxy-2-cyclohexen-1-one;5323-87-5;3-Ethoxycyclohex-2-enone;3-ethoxycyclohex-2-en-1-one;3-Ethoxy-2-cyclohexenone;2-Cyclohexen-1-one, 3-ethoxy-;3-Ethoxy-2-cyclohexene-1-one;3-Ethoxycyclohex-2-ene-1-one;3-Ethoxy-cyclohex-2-enone;AI3-17967;NSC-2826;EINECS 226-190-7;MFCD00001580;NSC2826;1-Ethoxycyclohexene-3-one;3-ethoxy-2-cyclohexen-one;DV46J47XJS;SCHEMBL99907;DTXSID30201326;3-Ethoxy-2-cyclohexenone, 99%;3-(ethyloxy)-2-cyclohexen-1-one;NSC 2826;AKOS004902428;CS-12385;SY048535;CS-0100015;E0384;FT-0615623;EN300-156157;A855563

Chemical Property of 3-Ethoxy-2-cyclohexen-1-one

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Vapor Pressure: 0.022mmHg at 25°C
• Refractive Index: 1.503-1.505
• Boiling Point: 250.1 °C at 760 mmHg
• Flash Point: 107.2 °C
• PSA: 26.30000
• Density: 1g/cm³
• LogP: 1.65980
• Storage Temp.: 0-6°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 140.083729621
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

3-Ethoxy-2-cyclohexen-1-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC1=CC(=O)CCC1
• Uses: 3-Ethoxy-2-cyclohexen-1-one is a useful intermediate for the preparation of 3-alkyl- or aryl-2-cyclohexen-1-ones, by addition of organometallic reagents and subsequent hydrolysis. It helps in kinetic enolate formation (LDA) and alkylation occurs at the 6-position, the Stork-Danheiser kinetic alkylation procedure, which has found extensive use in alicyclic synthesis.

Technology Process of 3-Ethoxy-2-cyclohexen-1-one

There total 23 articles about 3-Ethoxy-2-cyclohexen-1-one 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: 100.0%

ethanol (64-17-5) + 1,3-cylohexanedione (504-02-9) → 3-Ethoxycyclohex-2-en-1-one (5323-87-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 12h; Reflux;

DOI:10.1021/ol501421g

Reference yield: 92.0%

3-methoxycyclohex-2-en-1-one (16807-60-6) + ethanol (64-17-5) → 3-Ethoxycyclohex-2-en-1-one (5323-87-5)

Guidance literature:

With Amberlyst-15; at 80 ℃; under 2475.25 Torr;

DOI:10.1021/acs.oprd.9b00067

Reference yield: 91.0%

sodium ethanolate (141-52-6) + 3-<(Methanesulfonyl)oxy>-2-cyclohexenone (75700-18-4) → 3-Ethoxycyclohex-2-en-1-one (5323-87-5)

Guidance literature:

In ethanol; dichloromethane; for 1h;

DOI:10.1021/jo00314a051

upstream raw materials:

1,3-cylohexanedione

ethyl iodide

orthoformic acid triethyl ester

ethanol

Downstream raw materials:

3-butylcyclohexenone

2'-methyl-5,6-dihydro-[1,1'-bi(phenyl)]-3(4H)-one

3-biphenyl-3-yl-cyclohex-2-enone

3-methylcyclohexen-2-one

Refernces

• 1、 Tsuchimochi, Izuru,Hori, Shuhei,Takeuchi, Yasuo,Egi, Masahiro,Satoh, Tomo-O,Kanomata, Kyohei,Ikawa, Takashi,Akai, Shuji. "Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels-Alder Reaction". supporting information. p. 822 - 828. Retrieved 2021/02/16.
• 2、 Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu. "Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?". supporting information. p. 933 - 936. Retrieved 2021/03/03.