Cyclopentene, 1-pentyl-

Base Information

• Chemical Name: Cyclopentene, 1-pentyl-
• CAS No.: 4291-98-9
• Molecular Formula: C10H18
• Molecular Weight: 138.253
• Hs Code.: 2902199090
• DSSTox Substance ID: DTXSID60195562
• Nikkaji Number: J124.872C
• Wikidata: Q83068543
• Mol file: 4291-98-9.mol

Synonyms:1-Pentylcyclopentene;Cyclopentene, 1-pentyl-;1-Amyl-1-cyclopentene;4291-98-9;1-Pentylcyclopentene-1;1-Pentyl-1-cyclopentene;DTXSID60195562;QCNVZKGTZWZQPR-UHFFFAOYSA-N

Chemical Property of Cyclopentene, 1-pentyl-

Chemical Property:

• Vapor Pressure: 1.24mmHg at 25°C
• Melting Point: -83°C
• Refractive Index: 1.4494
• Boiling Point: 180°Cat760mmHg
• Flash Point: 51.3°C
• PSA: 0.00000
• Density: 0.827g/cm³
• LogP: 3.67700
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 138.140850574
• Heavy Atom Count: 10
• Complexity: 111

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=CCCC1

Technology Process of Cyclopentene, 1-pentyl-

There total 14 articles about Cyclopentene, 1-pentyl- 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: 65.0%

2-Pentyl-2-trifluoromethanesulfonyl-tetrahydro-thiopyran 1,1-dioxide (93915-96-9) → 1-n-pentylcyclopentene (4291-98-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ja00269a037

Reference yield: 10.0%

cyclopent-1-enylmethyl chloride (58729-25-2) + butyl magnesium bromide (693-04-9) → 1-n-pentylcyclopentene (4291-98-9) + (+)-(S)-1-butyl-2-methylenecyclopentane

Guidance literature:

cyclopent-1-enylmethyl chloride; With O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N,N-di-(S,S)-[2-phenylethylphosphoramidite]; copper(I) thiophene-2-carboxylate; In dichloromethane; at 20 ℃; Inert atmosphere;

butyl magnesium bromide; In diethyl ether; dichloromethane; at -78 ℃; for 5h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/adsc.200800086

Reference yield:

n-butylcopper (34948-25-9) + (+)-(S)-S-(1-cyclopen-1-ylmethyl)-N-methyl-S-phenylsulfoximine (131865-69-5) → 1-n-pentylcyclopentene (4291-98-9) + (+)-(S)-N-methyl benzenesulfinamide (33957-73-2) + (-)-(R)-1-butyl-2-methylenecyclopentane + (+)-(S)-1-butyl-2-methylenecyclopentane

Guidance literature:

With dimethylsulfide; boron trifluoride diethyl etherate; lithium iodide; In tetrahydrofuran; at -100 ℃; for 3h; Product distribution; Mechanism; other substituted organocopper and organocuprate reagents, other solvents, var. temp. and time;

DOI:10.1021/ja00114a009

upstream raw materials:

1-pentylcyclopentan-1-ol

2-Pentyl-2-trifluoromethanesulfonyl-tetrahydro-thiopyran 1,1-dioxide

n-butyllithium

(+)-(S)-S-(1-cyclopen-1-ylmethyl)-N-methyl-S-phenylsulfoximine

Downstream raw materials:

2-pentyl-2-cyclopenten-1-one

dihydro-cis-jasmone

3-Methyl-2-pentyl-cyclopent-2-enol

Refernces

• 1、 Falciola, Caroline A.,Tissot-Croset, Karine,Reyneri, Hugo,Alexakis, Alexandre. "β- and γ-disubstituted olefins: Substrates for copper-catalyzed asymmetric allylic substitution". supporting information; scheme or table. p. 1090 - 1100. Retrieved 2009/05/30.
• 2、 Gais, Hans-Joachim,Müller, Harald,Bund, J?rg,Scommoda, Matthias,Brandt, Jochen,Raabe, Gerhard. "Regio- and enantioselective substitution of primary endocyclic allylic sulfoximines with organocopper and organocuprate reagents. The importance of iodide for the allylic substitution with organocopper compounds". . p. 2453 - 2466. Retrieved 2007/10/02.