3-Methoxycyclohex-2-en-1-one

Base Information

• Chemical Name: 3-Methoxycyclohex-2-en-1-one
• CAS No.: 16807-60-6
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 2914509090
• European Community (EC) Number: 240-837-0
• UNII: TGG9T84Q2V
• DSSTox Substance ID: DTXSID40168471
• Nikkaji Number: J236.857I
• Wikidata: Q72489657
• Mol file: 16807-60-6.mol

Synonyms:3-methoxycyclohexenone

Chemical Property of 3-Methoxycyclohex-2-en-1-one

Chemical Property:

• Vapor Pressure: 0.0576mmHg at 25°C
• Refractive Index: 1.467
• Boiling Point: 232.9 °C at 760 mmHg
• Flash Point: 104.2 °C
• PSA: 26.30000
• Density: 1.03 g/cm³
• LogP: 1.26970
• Storage Temp.: Store below +30°C.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

3-Methoxycyclohex-2-enone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)CCC1
• General Description: 3-Methoxy-2-cyclohexen-1-one serves as a key intermediate in the total synthesis of (±)-α-acoradiene, where it undergoes regio- and stereoselective intramolecular photoaddition followed by reductive cyclobutane cleavage to form the spiro[4.5]decane system. Its reactivity in these transformations highlights its utility in constructing complex cyclic frameworks.

Technology Process of 3-Methoxycyclohex-2-en-1-one

There total 33 articles about 3-Methoxycyclohex-2-en-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%

methanol (67-56-1) + 3-Iodocyclohex-2-enone (56671-82-0) → 3-methoxycyclohex-2-en-1-one (16807-60-6)

Guidance literature:

With 2,3-dimethyl-buta-1,3-diene; triphenylphosphine; nickel dibromide; zinc; at 80 ℃; for 2h;

DOI:10.1016/S0040-4020(97)10205-8

Reference yield: 99.0%

methanol (67-56-1) + 1,3-cylohexanedione (504-02-9) → 3-methoxycyclohex-2-en-1-one (16807-60-6)

Guidance literature:

With Fe(OTs)3; at 20 ℃; for 4h;

DOI:10.1080/00397910802219361

Reference yield: 98.0%

methanol (67-56-1) + 3-Ethoxycyclohex-2-en-1-one (5323-87-5) → 3-methoxycyclohex-2-en-1-one (16807-60-6)

Guidance literature:

With iron(III) chloride hexahydrate; at 25 ℃; for 3h; Reagent/catalyst; Temperature; Catalytic behavior;

DOI:10.1039/c9ob00307j

upstream raw materials:

diazomethane

1,3-cylohexanedione

potassium ethoxide

dimethyl sulfate

Downstream raw materials:

3-(6-methoxy-[2]naphthyl)-cyclohex-2-enone

cyclohexenone

2-bromo-3-methoxy-2-cyclohexenone

3-(4-methoxyphenyl)-2-cyclohexen-1-one

Refernces

45. Total Synthesis of (+/-)-α-Acoradiene via Intramolecular Photoaddition and Reductive Cyclobutane Cleavage

10.1002/hlca.19830660213

The research details the total synthesis of (k)-a-acoradiene (4) from 3-methoxy-2-cyclohexenone through an 8-step process. The key steps involve a regio- and stereoselective photo [2 + 2] addition and reductive fragmentation. The purpose of the study was to develop a new, stereoselective approach to synthesizing the spiro [4.5] decane system, specifically targeting (k)-a-acoradiene. The researchers used key chemicals such as 3-methoxy-2-cyclohexenone, lithium/sodium alloy, t-butyl hydroperoxide, and lithium in ammonia. They also employed various reagents like N-chlorosuccinimide, dimethyl sulfide, and lithium tetramethylpiperidide. The conclusions drawn from the study confirmed the feasibility of the intramolecular photoaddition/cyclobutane fragmentation sequence for synthesizing complex structures like (k)-a-acoradiene. The researchers successfully synthesized the target compound and provided detailed structural evidence through spectral analysis.

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