56741-23-2

Basic information

• Product Name: 3-Nonanone, 1-phenyl-
• CAS NO: 56741-23-2
• Molecular Formula: C15H22O
• Molecular Weight: 218.339
• Mol File: 56741-23-2.mol
• Article Data: 23

Chemical Properties

• CAS DataBase Reference: 3-Nonanone, 1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nonanone, 1-phenyl-(56741-23-2)
• EPA Substance Registry System: 3-Nonanone, 1-phenyl-(56741-23-2)

Safety Data

• Hazardous Substances Data: 56741-23-2(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 201230-82-2 carbon monoxide 
• 638-45-9 1-Iodohexane 
• 6975-99-1 6-dodecyne 
• 256379-28-9 N-(3-methyl-2-pyridyl)-N-[(E)-3-phenyl-2-propenyl]amine 
• 592-41-6 1-hexene 
• 256379-33-6 C₂₁H₂₈N₂ 
• 103-64-0 bromostyrene 
• 111-27-3 hexan-1-ol 
• 4128-31-8 rac-octan-2-ol 
• 100-51-6 benzyl alcohol 
• 68-12-2 N,N-dimethyl-formamide 
• 3761-92-0 n-hexylmagnesium bromide 
• 645-45-4 hydrocinnamic acid chloride 

Downstream Products

• 95817-87-1 1-Phenethyl-1-<3-cyclohexyl-propyl>-heptan 

Relevant articles and documents

A Proton-Responsive Pyridyl(benzamide)-Functionalized NHC Ligand on Ir Complex for Alkylation of Ketones and Secondary Alcohols

A Cp*Ir(III) complex (1) of a newly designed ligand L1 featuring a proton-responsive pyridyl(benzamide) appended on N-heterocyclic carbene (NHC) has been synthesized. The molecular structure of 1 reveals a dearomatized form of the ligand. The protonation of 1 with HBF4 in tetrahydrofuran gives the corresponding aromatized complex [Cp*Ir(L1H)Cl]BF4 (2). Both compounds are characterized spectroscopically and by X-ray crystallography. The protonation of 1 with acid is examined by 1H NMR and UV-vis spectra. The proton-responsive character of 1 is exploited for catalyzing α-alkylation of ketones and β-alkylation of secondary alcohols using primary alcohols as alkylating agents through hydrogen-borrowing methodology. Compound 1 is an effective catalyst for these reactions and exhibits a superior activity in comparison to a structurally similar iridium complex [Cp*Ir(L2)Cl]PF6 (3) lacking a proton-responsive pendant amide moiety. The catalytic alkylation is characterized by a wide substrate scope, low catalyst and base loadings, and a short reaction time. The catalytic efficacy of 1 is also demonstrated for the syntheses of quinoline and lactone derivatives via acceptorless dehydrogenation, and selective alkylation of two steroids, pregnenolone and testosterone. Detailed mechanistic investigations and DFT calculations substantiate the role of the proton-responsive ligand in the hydrogen-borrowing process.

Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina

The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO2-Al2O3 was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.

Acceptorless dehydrogenation and dehydrogenative coupling of alcohols catalysed by protic NHC ruthenium complexes

A new family of protic NHC Ru complexes ligated with a phosphine-tethered imidazole moiety were prepared, which can act as excellent catalysts for acceptorless dehydrogenation of secondary alcohols and dehydrogenative coupling of primary and secondary alcohols, thus leading to the formation of a variety of carbonyl compounds with release of H2.