3-Nonen-2-one

Base Information

• Chemical Name: 3-Nonen-2-one
• CAS No.: 18402-83-0
• Molecular Formula: C9H16O
• Molecular Weight: 140.225
• European Community (EC) Number: 813-141-5,238-248-9
• UNII: FR0K39OF16
• DSSTox Substance ID: DTXSID201316311
• Nikkaji Number: J121.729A,J398.168A
• Wikidata: Q27278142
• Metabolomics Workbench ID: 5514
• Mol file: 18402-83-0.mol

Synonyms:3-NONEN-2-ONE;trans-3-Nonen-2-one;(E)-Non-3-en-2-one;14309-57-0;18402-83-0;(e)-3-nonen-2-one;3-Nonen-2-one, (3E)-;(3E)-NON-3-EN-2-ONE;non-3-en-2-one;(3E)-3-Nonen-2-one;3-Nonen-2-one [FHFI];3-Nonen-2-one, (E)-;FEMA No. 3955;3E-Nonen-2-one;UNII-FR0K39OF16;FR0K39OF16;EINECS 238-248-9;(3E)-nonen-2-one;3-Non-3-en-2-one;(E)-3-nonene-2-one;SCHEMBL159644;trans-3-Nonen-2-one, 95%;CHEBI:133457;DTXSID201316311;LMFA12000133;MFCD00010241;AKOS015916245;AS-56497;CS-0152368;N0592;D91739;EN300-7401434;A846998;A904004;J-011791;Q27278142

Chemical Property of 3-Nonen-2-one

Chemical Property:

• Appearance/Colour: COLORLESS TO YELLOW LIQUID
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 201.9 °C at 760 mmHg
• Flash Point: 81.3 °C
• PSA: 17.07000
• Density: 0.835 g/cm³
• LogP: 2.71190
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 140.120115130
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99.9% ^*data from raw suppliers

trans-3-Nonen-2-one ^*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: CCCCCC=CC(=O)C
• Isomeric SMILES: CCCCC/C=C/C(=O)C
• Uses: trans-3-Nonen-2-one is a useful reagent in the synthesis of olivetolic acid (O533005).

Technology Process of 3-Nonen-2-one

There total 35 articles about 3-Nonen-2-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: 93.0%

n-butyllithium (109-72-8,29786-93-4) + 2-ethoxy-1,4-pentadien-3-yl 2,2-dimethylpropanoate (132592-46-2) → (E)-non-3-en-2-one (18402-83-0)

Guidance literature:

With CuCN; In diethyl ether; at -20 ℃;

DOI:10.1021/jo00007a055

Reference yield: 84.0%

Acetic acid 1-(3-trimethylsilanyl-prop-1-ynyl)-hexyl ester (872885-07-9) → (E)-non-3-en-2-one (18402-83-0) + 4-acetoxy-non-2-yne (58879-43-9) + (E)-nona-1,3-dien-2-yl acetate (211996-13-3)

Guidance literature:

With isopropyl alcohol; (triphenylphosphine)gold(I) chloride; silver perchlorate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol0618151

Reference yield: 82.0%

hexanal (66-25-1) + 1-triphenylphosphoranylidene-2-propanone (1439-36-7) → (E)-non-3-en-2-one (18402-83-0)

Guidance literature:

With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 60 ℃; for 12h;

upstream raw materials:

(E)-4-chloro-3-buten-2-one

dipentylcadmium

hexanal

acetone

Downstream raw materials:

4-methyl-2-nonanone

4-phenylnonan-2-one

3-methylene-4-(methylthio)-2-pentyl-4-(trimethylsilyl)cyclobutyl methyl ketone

2-Nonanone

Refernces

• 1、 Ekogha, C. Bibang Bi,Ruel, O.,Julia, S. A.. "REACTIVITY OF THE 1-t.BUTYLTHIO-3-METHOXY-1-ALKENES TOWARDS METALATING AGENTS, I. REGIOSELECTIVE DEPROTONATION AT EITHER ONE OF THE TWO OLEFINIC SITES OF THE Z-ISOMERS". . p. 4825 - 4828. Retrieved 1983.
• 2、 Wang, Tianze,Zhen, Dawei,Tan, Jia,Xie, Jianchun,Cheng, Jie,Zhao, Jian. "Characterization of initial reaction intermediates in heated model systems of glucose, glutathione, and aliphatic aldehydes". . . Retrieved 2019/09/12.
• 3、 Khopade, Tushar M.,Warghude, Prakash K.,Mete, Trimbak B.,Bhat, Ramakrishna G.. "Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones". supporting information. p. 197 - 200. Retrieved 2018/12/13.