5422-88-8

Basic information

• Product Name: CYCLOPENTYL PHENYL KETONE
• Synonyms: TIMTEC-BB SBB007885;CYCLOPENTYLPHENYLMETHANONE;CYCLOPENTYL PHENYL KETONE;BENZOYLCYCLOPENTANE;Cyclopentanylphenylmethanone;cyclopentylphenyl-methanon;Ketone, cyclopentyl phenyl;Cyclopentylphenylketone,96%
• CAS NO: 5422-88-8
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• EINECS: 226-548-2
• Product Categories: Pharmaceutical Intermediates;Aromatic Ketones (substituted)
• Mol File: 5422-88-8.mol

Chemical Properties

• Boiling Point: 136-140°C 16mm
• Flash Point: >110°C
• Appearance: /
• Density: 1,036 g/cm3
• Vapor Pressure: 0.00556mmHg at 25°C
• Refractive Index: 1.5440
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• BRN: 2045903
• CAS DataBase Reference: CYCLOPENTYL PHENYL KETONE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPENTYL PHENYL KETONE(5422-88-8)
• EPA Substance Registry System: CYCLOPENTYL PHENYL KETONE(5422-88-8)

Safety Data

• Safety Statements: 23-24/25
• TSCA: Yes
• Hazardous Substances Data: 5422-88-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Cyclopentyl Phenyl Ketone is used as a key intermediate for the synthesis of synthetic hydrochloric acid amyl ethyl quin ether, which is a pharmaceutical compound.
Used in Organic Chemistry:
Cyclopentyl Phenyl Ketone is used in the preparation of ortho-arylated compounds and phenanthrones through palladium-catalyzed chelation-assisted C-H activation. This application is significant in the field of organic chemistry for the synthesis of complex organic molecules.
Used in Research and Forensic Applications:
As an analytical reference standard, Cyclopentyl Phenyl Ketone is utilized in research and forensic applications to study its properties and potential uses in various chemical and pharmaceutical processes.

Synthesis

In 100ml round-bottomed flask, by 2-cyclopenta ethyl benzoylacetate (10.6g, 43.05mmol, 1.0eq), NaOH (2.6g, 64.5mmol) and Na2CO3(4.5g, 43mmol), is suspended in 50.0mLH2In O, it is warmed up to 80 DEG C and reacts 3 hours, obtain product phenylcyclopentyl ketone.Purify: reactant liquor is cooled to room temperature, extract 3 times with ethyl acetate 20mL；Organic phase saturated sodium-chloride washs, and merges organic phase and uses anhydrous MgSO4Being dried, then remove solvent under reduced pressure, obtain thick product, column chromatography purifies, and eluant, eluent is ethyl acetate: petroleum ether (1:10), obtains 6.54g target product, yield 87.2%.

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

Upstream product

• 110480-94-9 cyclopentylphenylmethanol 
• 52217-42-2 (1-chloro-cyclopentyl)-phenyl ketone 
• 100-47-0 benzonitrile 
• 33240-34-5 cyclopentylmagnesium bromide 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 71-43-2 benzene 
• 771-98-2 1-Phenylcyclohexene 
• 98815-42-0 2-(α-aminobenzylidene)cyclopentanone 
• 1056477-06-5 2-bromocyclohexanone 
• 67-56-1 methanol 
• 4829-01-0 (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide 
• 21573-70-6 (cyclopent-1-en-1-yl)(phenyl)methanone 
• 946-01-0 ε-chlorohexanophenone 
• 82777-11-5 6-bromo-1-phenyl-1-hexanone 

Downstream Products

• 97703-99-6 1-cyclopentyl-1-phenyl-ethanol 
• 94571-10-5 6-phenyl-spiro[4.5]dec-6-en-8-one 
• 41848-73-1 phenyl(1-phenylcyclopentyl)methanone 
• 110480-94-9 cyclopentylphenylmethanol 
• 6740-66-5 (1-bromocyclopentyl)(phenyl)methanone 
• 83568-09-6 cyclopentyl phenyl ketoxime 
• 52217-42-2 (1-chloro-cyclopentyl)-phenyl ketone 
• 108516-23-0 [α-2H]cyclopentyl phenyl ketone 
• 23459-36-1 1-phenyl-cyclopentylmethylamine 
• 5700-46-9 1-cyclopentyl-1,2-diphenyl-ethene 
• 1225-91-8 1-Cyclopentyl-1-phenyl-2--aethylen 
• 16583-17-8 1-cyclopentyl-1-hydroxy-1-phenyl propyne 
• 129527-96-4 (2-Nitro-1-phenylethylidene)cyclopentane 
• 119497-39-1 Cyclopentyl-[2-(5-diethylamino-pent-3-ynyl)-[1,3]dithian-2-yl]-phenyl-methanol 

Relevant articles and documents

A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids

Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.

C(sp3)-H Bond Acylation with N -Acyl Imides under Photoredox/ Nickel Dual Catalysis

A novel Ni/photoredox-catalyzed acylation of aliphatic substrates, including simple alkanes and dialkyl ethers, has been developed. The method combines C-N bond activation of amides with a radical relay mechanism involving hydrogen-atom transfer. The protocol is operationally simple, employs bench-stable N -acyl imides as acyl-transfer reagents, and permits facile access to alkyl ketones under very mild conditions.

ARYLCYCLOHEXYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PSYCHIATRIC DISORDERS

Provided herein are arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders.

Aerobic oxidation and oxidative esterification of alcohols through cooperative catalysis under metal-free conditions

The ABNO@PMO-IL-Br material obtained by anchoring 9-azabicyclo[3.3.1]nonane-3-oneN-oxyl (keto-ABNO) within the mesopores of periodic mesoporous organosilica with bridged imidazolium groups is a robust bifunctional catalyst for the metal-free aerobic oxidation of numerous primary and secondary alcohols under oxygen balloon reaction conditions. The catalyst, furthermore, can be successfully employed in the first metal-free self-esterification of primary aliphatic alcohols affording valued esters.

Ir(NHC)-Catalyzed Synthesis of β-Alkylated Alcohols via Borrowing Hydrogen Strategy: Influence of Bimetallic Structure

Multi N-heterocyclic carbene(NHC)-modified iridium catalysts were employed in the β-alkylation of alcohols; dimerization of primary alcohols (Guerbet reaction), cross-coupling of secondary and primary alcohols, and intramolecular cyclization of alcohols. Mechanistic studies of Guerbet reaction, including kinetic experiments, mass analysis, and density functional theory (DFT) calculation, were employed to explain the fast reaction promoted by bimetallic catalysts, and the dramatic reactivity increase of monometallic catalysts at the late stage of the reaction. (Figure presented.).

Synergistic Activation of Amides and Hydrocarbons for Direct C(sp3)–H Acylation Enabled by Metallaphotoredox Catalysis

The utilizations of omnipresent, thermodynamically stable amides and aliphatic C(sp3)?H bonds for various functionalizations are ongoing challenges in catalysis. In particular, the direct coupling between the two functional groups has not been realized. Here, we report the synergistic activation of the two challenging bonds, the amide C?N and unactivated aliphatic C(sp3)?H, via metallaphotoredox catalysis to directly acylate aliphatic C?H bonds utilizing amides as stable and readily accessible acyl surrogates. N-acylsuccinimides served as efficient acyl reagents for the streamlined synthesis of synthetically useful ketones from simple C(sp3)?H substrates. Detailed mechanistic investigations using both computational and experimental mechanistic studies were performed to construct a detailed and complete catalytic cycle. The origin of the superior reactivity of the N-acylsuccinimides over other more reactive acyl sources such as acyl chlorides was found to be an uncommon reaction pathway which commences with C?H activation prior to oxidative addition of the acyl substrate.

One-pot formal dehydrogenative ketone synthesis from aldehydes and non-activated hydrocarbons

Ketones are a fundamental functionality found throughout a range of natural and synthetic compounds, making their synthesis essential throughout the chemical disciplines. Herein, we describe a one-pot synthesis of ketones via decatungstate-mediated formal dehydrogenative coupling between aldehydes and non-activated hydrocarbons. A variety of substituted benzaldehydes and cycloalkanes could be used in the optimized reaction to produce the desired ketones in moderate yields. The decatungstate photocatalyst functions in two reactions in this synthesis, catalyzing both the coupling and oxidation steps of the process. Notably, the reaction displays both high atom economy and sustainability, as it uses light and oxygen as key energy sources.

Catalytic Asymmetric Acyloin Rearrangements of α-Ketols, α-Hydroxy Aldehydes, and α-Iminols by N, N′-Dioxide-Metal Complexes

A highly enantioselective acyloin rearrangement of cyclic α-ketols has been developed with a chiral Al(III)-N,N′-dioxide complex as catalyst. This strategy provided an array of optically active 2-acyl-2-hydroxy cyclohexanones in moderate to good yields with high enantioselectivities. The asymmetric isomerizations of acyclic α-hydroxy aldehydes and α-iminols were achieved as well under modified conditions, affording the corresponding chiral α-hydroxy ketones and α-amino ketones in moderate results. Moreover, further transformations of product to enantioenriched diols were carried out.

Iron-Catalyzed Cleavage Reaction of Keto Acids with Aliphatic Aldehydes for the Synthesis of Ketones and Ketone Esters

The radical–radical coupling reaction is an important synthetic strategy. In this study, the iron-catalyzed radical–radical cross-coupling reaction based on the decarboxylation of keto acids and decarbonylation of aliphatic aldehydes to obtain valuable aryl ketones is reported for the first time. Remarkably, when tertiary aldehydes were used as carbonyl sources, ketone esters were selectively obtained instead of ketones. The gram-scale preparation of aryl ketone through this strategy was easily achieved by using only 3 mol % of the iron catalyst. As a proof-of-concept, the bioactive molecule flurprimidol was synthesized in two steps by using this strategy.

Method for preparing aryl ketone based on iron-catalyzed free radical-free radical coupling reaction such as ketonic acid decarboxylation and fatty aldehyde de-carbonylation

The invention discloses a method for preparing an aryl ketone derivative based on a free radical-free radical cross-coupling reaction such as ketonic acid decarboxylation and fatty aldehyde de-carbonylation. The method comprises the following steps: reacting aryl-substituted ketonic acid with fatty aldehyde under the catalytic action of ferric triacetylacetonate to generate an aryl ketone derivative; the gram-grade reaction can be realized by the method only by using 3mol% of an iron catalyst; and the method has the advantages of no need of consumption of a large amount of a Lewis acid catalyst or a stoichiometric organic metal reagent, mild reaction conditions, one-step reaction, few by-products, wide substrate application range and scalable reaction, and overcomes the defects of large catalyst consumption, insufficient functional group tolerance, many by-products and the like in the prior art.