1-Acetoxy-2-pentylcyclopentene

Base Information

• Chemical Name: 1-Acetoxy-2-pentylcyclopentene
• CAS No.: 24851-93-2
• Molecular Formula: C12H20 O2
• Molecular Weight: 196.29
• DSSTox Substance ID: DTXSID20885275
• Nikkaji Number: J422.146J
• Wikidata: Q82863889
• Mol file: 24851-93-2.mol

Synonyms:1-Acetoxy-2-pentylcyclopentene;24851-93-2;1-Cyclopenten-1-ol, 2-pentyl-, acetate;1-Cyclopenten-1-ol, 2-pentyl-, 1-acetate;SCHEMBL18982985;DTXSID20885275;2-Pentyl-1-cyclopenten-1-ol acetate

Chemical Property of 1-Acetoxy-2-pentylcyclopentene

Chemical Property:

• Vapor Pressure: 0.00349mmHg at 25°C
• Boiling Point: 281.8°C at 760 mmHg
• Flash Point: 113.3°C
• PSA: 26.30000
• Density: 0.95g/cm³
• LogP: 3.56780
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 196.146329876
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=C(CCC1)OC(=O)C

Technology Process of 1-Acetoxy-2-pentylcyclopentene

There total 8 articles about 1-Acetoxy-2-pentylcyclopentene 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: 15.0%

2-pentyl-cyclopentanone (4819-67-4) + acetic anhydride (108-24-7) → 2-pentylcyclopent-1-en-1-yl acetate (24851-93-2) + 2-acetyl-2-pentylcyclopentanone (79665-02-4)

Guidance literature:

With toluene-4-sulfonic acid; at 110 - 125 ℃; for 6h;

DOI:10.1021/jo00340a009

Reference yield:

Isopropenyl acetate (108-22-5) + 2-pentyl-cyclopentanone (4819-67-4) → 2-pentylcyclopent-1-en-1-yl acetate (24851-93-2) + C12H20O2

Guidance literature:

With toluene-4-sulfonic acid; at 90 ℃; Overall yield = 70 %; Overall yield = 295 mg;

DOI:10.1016/j.tet.2016.04.011

Reference yield:

1-Bromopentane (110-53-2) → 2-pentylcyclopent-1-en-1-yl acetate (24851-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) NaH, (ii) /BRN= 1730981/

2: HCl / acetic acid

3: TsOH

With hydrogenchloride; toluene-4-sulfonic acid; In acetic acid;

DOI:10.1021/jo00931a045

upstream raw materials:

2-pentyl-cyclopentanone

acetic anhydride

Isopropenyl acetate

1-Bromopentane

Downstream raw materials:

(+/-)-methyl trans-dihydrojasmonate

(+/-)-methyl dihydroepijasmonate

methyl 1-hydroxy-2-pentylcyclopent-2-eneacetate

methyl 1-carboxymethyl-1-(2-pentyl-3-oxocyclopentyl)acetate

Refernces

• 1、 -. "METHODS OF PREPARING a,?-UNSATURATED OR a-HALO KETONES AND ALDEHYDES". Paragraph 0087; 0090; 0091-0093. . Retrieved 2017/07/14.
• 2、 Torii, Sigeru,Inokuchi, Tsutomu,Oi, Ryu. "Electrooxidative Cleavage of Carbon-Carbon Linkages. 1. Preparation of Acylic Oxoalkanoates from 2-Hydroxy- and 2-Acetoxy-1-cycloalkanones and Cycloalkanone Enol Acetates". . p. 47 - 52. Retrieved 2007/10/02.