34993-51-6

Basic information

• Product Name: (R)-3-PHENYLCYCLOHEXANONE
• Synonyms: (R)-3-PHENYLCYCLOHEXANONE;(3R)-3-Phenylcyclohexanone;(R)-3-Phenylcyclohexanone,99%e.e.
• CAS NO: 34993-51-6
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• Product Categories: Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry
• Mol File: 34993-51-6.mol
• Article Data: 196

Chemical Properties

• Boiling Point: 294.012°C at 760 mmHg
• Flash Point: 123.664°C
• Appearance: /
• Density: 1.043g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: Refrigerator
• CAS DataBase Reference: (R)-3-PHENYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-PHENYLCYCLOHEXANONE(34993-51-6)
• EPA Substance Registry System: (R)-3-PHENYLCYCLOHEXANONE(34993-51-6)

Safety Data

• Hazardous Substances Data: 34993-51-6(Hazardous Substances Data)

Usage

Description

(R)-3-Phenylcyclohexanone, with the CAS number 34993-51-6, is a chemical compound resulting from a single-step reaction between 2-Cyclohexen-1-one (CAS number 930-68-7) and Potassium Phenyltrifluoroborate (CAS number 153766-81-5). It is an essential building block in the synthesis of various organic compounds and has unique properties that make it valuable in different applications.

Uses

Used in Chiral Porous Organic Frameworks (POFs) Industry:
(R)-3-Phenylcyclohexanone is used as a key component in the preparation of chiral porous organic frameworks (POFs) for asymmetric heterogeneous catalysis. Its presence in the POFs contributes to the selective adsorption and separation of chiral molecules, which is crucial in the production of enantiomerically pure compounds, essential in pharmaceuticals and agrochemicals.
Used in Gas Chromatography Industry:
(R)-3-Phenylcyclohexanone is also utilized in the field of gas chromatography for the separation of complex mixtures. Its unique chemical properties allow for the efficient and accurate separation of various components in a mixture, making it a valuable tool in analytical chemistry and quality control processes.

InChI:InChI=1/C12H14O/c13-12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2/t11-/m1/s1

Upstream product

• 396718-95-9 [(R)-3-Phenyl-cyclohex-(E)-ylidene]-acetaldehyde 
• 930-68-7 cyclohexenone 
• 3262-89-3 triphenylboroxine 
• 780-69-8 triethoxyphenylsilane 
• 873223-22-4 diphenylindium hydroxide 
• 853955-69-8 [2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane 
• 100-58-3 phenylmagnesium bromide 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 13197-81-4 dimethyl(phenyl)aluminum 
• 23665-09-0 phenylzinc iodide 
• 591-50-4 iodobenzene 
• 28557-00-8 phenylzinc chloride 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 1232059-56-1 C₁₃H₁₅N 
• 1232059-70-9 (1S,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-79-8 C₁₃H₁₉N 
• 1232059-68-5 (1R,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-66-3 C₁₃H₁₆O₂ 
• 76936-85-1 (+)-(R)-3-phenyl-1-(2-tolyl)cyclohexene 

Relevant articles and documents

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions

Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.

Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes

Transition-metal-catalyzed reductive coupling reactions have emerged as powerful protocols to construct C-C bonds. However, the development of enantioselective C(sp3)-C(sp3) reductive coupling remains challenging. Herein, we report a highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates through cooperative palladium and photoredox catalysis using diisopropylethylamine or Hantzsch ester as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)-C(sp3) bonds under mild reaction conditions. A series of C2-symmetrical chiral 1,5-dienes were easily prepared with excellent enantioselectivities (up to >99% ee), diastereoselectivities (up to >95:5 dr), and regioselectivities (up to >95:5 rr). The resultant chiral 1,5-dienes can be directly used as chiral ligands in asymmetric synthesis, and they can be also transformed into other valuable chiral ligands.