(R)-3-Phenylcyclopentanone

Base Information

• Chemical Name: (R)-3-Phenylcyclopentanone
• CAS No.: 86505-44-4
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.216
• Hs Code.: 2914399090
• European Community (EC) Number: 678-441-9
• DSSTox Substance ID: DTXSID20452481
• Nikkaji Number: J1.040.788E
• Wikidata: Q82273143
• Mol file: 86505-44-4.mol

Synonyms:(R)-3-Phenylcyclopentanone;86505-44-4;(r)-3-phenylcyclopentan-1-one;(3R)-3-PHENYLCYCLOPENTAN-1-ONE;(R)-3-phenyl-cyclopentanone;SCHEMBL4864740;(R)-3alpha-Phenylcyclopentanone;(R,S)-3-Phenyl-cyclopentanone;DTXSID20452481;MFBXYJLOYZMFIN-SNVBAGLBSA-N;MFCD08276412;AKOS015840448;AS-43808;CS-0330815;P1504

Chemical Property of (R)-3-Phenylcyclopentanone

Chemical Property:

• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 90 ° (C=0.5, CHCl3)
• Boiling Point: 276.102oC at 760 mmHg
• Flash Point: 114.891oC
• PSA: 17.07000
• Density: 1.072g/cm3
• LogP: 2.52320
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 160.088815002
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

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

(R)-3-Phenylcyclopentanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)CC1C2=CC=CC=C2
• Isomeric SMILES: C1CC(=O)C[C@@H]1C2=CC=CC=C2

Technology Process of (R)-3-Phenylcyclopentanone

There total 142 articles about (R)-3-Phenylcyclopentanone 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: 100.0%

cyclopent-2-enone (930-30-3) + phenylboronic acid (98-80-6) → (R)-3-phenylcyclopentanone (64145-51-3,86505-50-2,141662-68-2,86505-44-4)

Guidance literature:

With chlorobis(ethylene)rhodium(I) dimer; (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; potassium hydroxide; In methanol; dichloromethane; at 20 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.200907033

Reference yield: 99.0%

cyclopent-2-enone (930-30-3) + phenylboronic acid (98-80-6) → (S)-3-phenylcyclopentanone (64145-51-3,86505-44-4,141662-68-2,86505-50-2)

Guidance literature:

With potassium phosphate; chlorobis(ethylene)rhodium(I) dimer; C₂₅H₂₇NO₃S; In 1,4-dioxane; water; at 60 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c1cc12322j

Reference yield: 99.0%

cyclopent-2-enone (930-30-3) + potassium phenyltrifluoborate → (S)-3-phenylcyclopentanone (64145-51-3,86505-44-4,141662-68-2,86505-50-2)

Guidance literature:

With chlorobis(ethylene)rhodium(I) dimer; C₁₉H₂₄O; triethylamine; potassium hydroxide; In methanol; water; toluene; at 20 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ol901321r

upstream raw materials:

4-phenyl-4-penten-1-al

diphenylmagnesium

2-[(S)-(4-methylphenyl)sulfinyl]cyclopent-2-en-1-one

((R)-3-Methylene-cyclopentyl)-benzene

Downstream raw materials:

(3R)-phenylcyclopentanone-2,2,5,5-d4

(S)-3-phenyl-cyclopentylamine

(S)-3-phenylcyclopentanone-2,2,5,5-d4

(4R)-phenylcyclopentene-1,3,3-d3

Refernces

• 1、 Chen, Chen,Hayashi, Tamio,Meng, He,Ming, Jialin,Sun, Chao,Wei, Haili. "Asymmetric Synthesis of Chiral Bicyclo[2.2.1]hepta-2,5-diene Ligands through Rhodium-Catalyzed Asymmetric Arylative Bis-cyclization of a 1,6-Enyne". supporting information. p. 6311 - 6315. Retrieved 2021/09/02.
• 2、 Nikol, Alexander,Zhang, Ziyun,Chelouan, Ahmed,Falivene, Laura,Cavallo, Luigi,Herrera, Alberto,Heinemann, Frank W.,Escalona, Ana,Frie?, Sibylle,Grasruck, Alexander,Dorta, Romano. "Tricyclic Sulfoxide-Alkene Hybrid Ligands for Chiral Rh(I) Complexes: The "Matched" Diastereomer Catalyzes Asymmetric C-C Bond Formations". supporting information. p. 1348 - 1359. Retrieved 2020/03/30.