2-Allylcyclohexanone

Base Information

• Chemical Name: 2-Allylcyclohexanone
• CAS No.: 94-66-6
• Deprecated CAS: 115182-22-4
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• Hs Code.: 29142990
• European Community (EC) Number: 202-352-2
• NSC Number: 128921
• DSSTox Substance ID: DTXSID90883283
• Nikkaji Number: J182.106G
• Mol file: 94-66-6.mol

Synonyms:2-Allylcyclohexanone;94-66-6;Cyclohexanone, 2-(2-propenyl)-;2-Allylcyclohexan-1-one;Cyclohexanone, 2-allyl-;2-prop-2-enylcyclohexan-1-one;Cyclohexanone, 2-(2-propen-1-yl)-;EINECS 202-352-2;NSC 128921;2-(prop-2-en-1-yl)cyclohexan-1-one;AI3-07009;2-(2-Propenyl)cyclohexanone;NSC128921;2-allyl cyclohexanone;2-allyl-cyclohexanone;2-allylcyclohexan-1-on;2-allyl-cyclohexan-1-one;2-Allylcyclohexanone, 97%;2-(2-propenyl)-cyclohexanon;SCHEMBL528992;2-Allylcyclohexanone, >/=97%;DTXSID90883283;2-(prop-2-en-1-yl)cyclohexanone;MFCD00043548;STL301914;AKOS009156864;NSC-128921;AS-35729;CS-0204777;FT-0610994;EN300-268221;F8882-7572;115182-22-4

Chemical Property of 2-Allylcyclohexanone

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 0.378mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• Boiling Point: 197.5 °C at 760 mmHg
• Flash Point: 69.3 °C
• PSA: 17.07000
• Density: 0.909 g/cm³
• LogP: 2.32180
• Water Solubility.: Insoluble
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 138

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Allylcyclohexanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC1CCCCC1=O
• Uses: 2-Allylcyclohexanone may be used in the synthesis of the following:bicyclo[3.3.1]non-2-en-9-oneR-(-)-epilachnene, an antipode of the defensive droplets from the Mexican bean beetle, Epilachna varivestis

Technology Process of 2-Allylcyclohexanone

There total 159 articles about 2-Allylcyclohexanone 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: 98.0%

allyl cyclohex-1-en-1-yl carbonate (86950-86-9) → 2-allylcyclohexan-1-one (94-66-6)

Guidance literature:

tetrakis(triethylphosphite)nickel⁽⁰⁾; In tetrahydrofuran; at 65 ℃; for 1h;

DOI:10.1246/cl.1984.1721

Reference yield: 95.0%

Allyl acetate (591-87-7) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-allylcyclohexan-1-one (94-66-6)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dimethyl sulfoxide; at 20 ℃; for 16h;

DOI:10.1002/anie.200504021

Reference yield: 95.0%

1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1) + allyl bromide (106-95-6) → 2-allylcyclohexan-1-one (94-66-6)

Guidance literature:

In 1,4-dioxane; at 0 ℃; for 4h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetasy.2016.11.010

upstream raw materials:

pyrrolidine

cyclohexanone

allyl bromide

ethyl 1-allyl-2-oxocyclohexanecarboxylate

Downstream raw materials:

2,2-diallylcyclohexanone

6-Allyl-2-cyclohexenone

Bicyclo[3.3.1]non-2-en-9-one

2-allyl-cyclohex-2-enone

Refernces

• 1、 Jones,Ando. "". . p. 2200. Retrieved 1968.
• 2、 Wu, Zhao,Xu, Xiaolong,Wang, Jianchun,Dong, Guangbin. "Carbonyl 1,2-transposition through triflate-mediated a-amination". . p. 734 - 740. Retrieved 2021/11/16.
• 3、 Huynh, Uyen,McDonald, Stacey L.,Lim, Daniel,Uddin, Md. Nasir,Wengryniuk, Sarah E.,Dey, Sumit,Coltart, Don M.. "Formation, Alkylation, and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: An Approach to the Enantioselective α-Alkylation of Ketones". . p. 12951 - 12964. Retrieved 2018/11/30.