3-Isopropylcyclopentanone

Base Information

• Chemical Name: 3-Isopropylcyclopentanone
• CAS No.: 10264-56-9
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.199
• European Community (EC) Number: 854-503-2
• Nikkaji Number: J1.930.803K
• Mol file: 10264-56-9.mol

Synonyms:3-isopropylcyclopentanone;10264-56-9;3-(propan-2-yl)cyclopentan-1-one;3-propan-2-ylcyclopentan-1-one;3-ISOPROPYLCYCLOPENTAN-1-ONE;SCHEMBL1823080;PYAUPTMCTBUIGA-UHFFFAOYSA-N;AKOS013846583;EN300-177998

Chemical Property of 3-Isopropylcyclopentanone

Chemical Property:

• Boiling Point: 174.438 °C at 760 mmHg
• PSA: 17.07000
• Density: 0.919 g/cm³
• LogP: 2.01160
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 116

Purity/Quality:

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

3-(Propan-2-yl)cyclopentan-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CCC(=O)C1

Technology Process of 3-Isopropylcyclopentanone

There total 74 articles about 3-Isopropylcyclopentanone 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: 89.0%

cyclopent-2-enone (930-30-3) + isopropylmagnesium chloride (1068-55-9) → 3-isopropylcyclopentanone (64847-89-8,93451-74-2,93451-75-3,10264-56-9)

Guidance literature:

With copper(l) iodide; (4-(S)-isopropyl-2-Ph-oxazoline-2'-Se)2; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃;

DOI:10.1016/S0040-4039(02)01713-6

Reference yield: 87.0%

3-isopropyl-cyclopent-2-enone (1619-28-9) → 3-(R)-(2'-methylethyl)-cyclopentanone (10264-56-9,64847-89-8,93451-75-3,93451-74-2) + 3-(S)-(2-methylethyl)-cyclopentanone (10264-56-9,64847-89-8,93451-74-2,93451-75-3)

Guidance literature:

3-isopropyl-cyclopent-2-enone; With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In toluene; at 0 ℃; for 96h;

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; diethyl ether; toluene; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo026605q

Reference yield: 87.0%

3-isopropyl-cyclopent-2-enone (1619-28-9) → 3-(R)-(2'-methylethyl)-cyclopentanone (10264-56-9,64847-89-8,93451-75-3,93451-74-2) + 3-(S)-(2-methylethyl)-cyclopentanone (10264-56-9,64847-89-8,93451-74-2,93451-75-3)

Guidance literature:

3-isopropyl-cyclopent-2-enone; With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; copper(l) chloride; sodium t-butanolate; polymethylhydrosiloxane; In toluene; at 0 ℃; for 96h;

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; diethyl ether; toluene; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jo026605q

upstream raw materials:

(+-)-3-isopropyl-adipic acid

3-isopropyl-cyclopent-2-enone

1-isopropyl-cyclopentanol-⁽³⁾

1-hydroxy-3-isopropyl-cyclopentanecarboxylic acid

Downstream raw materials:

2,5-dibenzylidene-3-isopropyl-cyclopentanone

(S)-2,5-dibenzylidene-3-isopropyl-cyclopentanone

(1R)-1-isopropyl-2.4-di-(benzylidene-(ξ))-cyclopentanone-(3)

(+/-)-1-isopropyl-2.4-dibenzylidene-cyclopentanone-(3)

Refernces

• 1、 Nakazaki,M.,Ikematsu,K.. "-". . p. 459 - 464. Retrieved 1964.
• 2、 Smith,W.B.,Gonzalez,C.. "-". . p. 3541 - 3542. Retrieved 1963.
• 3、 Wu,Funakoshi,Sakai. "Highly enantioselective cyclization using cationic Rh(I) with chiral ligand". . p. 6331 - 6334. Retrieved 1992.
• 4、 Shin, Minkyeong,Gu, Minji,Lim, Sung Soo,Kim, Min-Jae,Lee, JuHyung,Jin, HyeongGyu,Jang, Yun Hee,Jung, Byunghyuck. "CuI-Catalysed Enantioselective Alkyl 1,4-Additions to (E)-Nitroalkenes and Cyclic Enones with Phosphino-Oxazoline Ligands". . p. 3122 - 3130. Retrieved 2018/07/06.
• 5、 Santos Pisoni, Diego dos,Sobieski da Costa, Jessé,Gamba, Douglas,Petzhold, Cesar Liberato,César de Amorim Borges, Antonio,Ceschi, Marco Antonio,Lunardi, Paula,Saraiva Gon?alves, Carlos Alberto. "Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones". experimental part. p. 526 - 535. Retrieved 2010/04/06.