21573-69-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Phenylcyclopentanecarboxaldehyde serves as a crucial building block in the synthesis of a wide range of pharmaceuticals. Its chemical structure allows for the development of new drugs with potential therapeutic effects, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Phenylcyclopentanecarboxaldehyde is utilized in the creation of various agrochemicals. Its incorporation into these products can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Fragrance Industry:
1-Phenylcyclopentanecarboxaldehyde also plays a significant role in the fragrance industry, where it is used to develop unique and complex scents for perfumes, cosmetics, and other scented products. Its ability to contribute to the overall aroma profile makes it a sought-after ingredient in the formulation of fragrances.
Used as a Flavoring Agent in Food Industry:
1-Phenylcyclopentanecarboxaldehyde is employed as a flavoring agent in the food industry, adding depth and complexity to the taste of various food products. Its unique flavor profile can enhance the overall sensory experience of food and beverages.
Used in Biological Research:
1-Phenylcyclopentanecarboxaldehyde has been studied for its potential biological activities, such as antioxidant and anti-inflammatory properties. Researchers are exploring its applications in the development of treatments for various diseases and conditions, leveraging its inherent biological effects.
However, it is important to note that 1-Phenylcyclopentanecarboxaldehyde can be irritating to the skin, eyes, and respiratory system. Therefore, proper handling and safety precautions are essential when working with this chemical compound in any of its applications.

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

Upstream product

• 17380-62-0 1-phenylcyclopentanecarboxylic acid chloride 
• 110-52-1 1,4-dibromo-butane 
• 26939-22-0 2-benzyl-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine 
• 5775-23-5 1-phenylcyclohexene oxide 
• 64-17-5 ethanol 
• 19324-77-7 2-chloro-1-phenylcyclohexan-1-ol 
• 122-78-1 phenylacetaldehyde 
• 4410-77-9 benzylidenecyclopentane 
• 108-86-1 bromobenzene 
• 52305-68-7 1-phenylcyclohexane-1,2-diol 
• 533-60-8 cyclohexanone-2-ol 
• 110-60-1 1,4-diaminobutane 
• 77-55-4 1-phenyl-1-cyclopentanecarboxylic acid 
• 59115-90-1 1-hydroxymethyl-1-phenylcyclopentane 

Downstream Products

• 77-55-4 1-phenyl-1-cyclopentanecarboxylic acid 
• 59115-90-1 1-hydroxymethyl-1-phenylcyclopentane 
• 5407-84-1 β-phenyl-β,β-tetramethylenepropionitrile 
• 100611-61-8 (1-phenyl-cyclopentyl)-acetaldehyde 
• 101266-82-4 1-(1-phenyl-cyclopentyl)-ethanol 
• 1616922-83-8 5-(benzyloxy)-6-hydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4-carboxylic acid 
• 1616922-81-6 5-benzyloxy-6-hydroxy-2-(1-phenylcyclopentylmethyl)pyrimidine-4-carboxylic acid tert-butyl ester 
• 1616922-79-2 2-(1-phenylcyclopentyl)acetamidine hydrochloride 
• 1616924-78-7 5-benzyloxy-6-hydroxy-2-(1-phenylcyclopentylmethyl)pyrimidine-4-carboxylic acid [2-(tert-butyldimethylsilanyloxy)ethyl](4-fluorobenzyl)amide 
• 1616924-76-5 5-benzyloxy-6-hydroxy-2-(1-phenylcyclopentylmethyl)pyrimidine-4-carboxylic acid [2-(tert-butyldimethylsilanyloxy)ethyl](tetrahydropyran-4-yl)amide 
• 1616924-72-1 5-benzyloxy-6-hydroxy-2-(1-phenylcyclopentylmethyl)pyrimidine-4-carboxylic acid [2-(tert-butyldimethylsilanyloxy)ethyl]cyclopropylmethylamide 
• 1616924-69-6 5-benzyloxy-6-hydroxy-2-(1-phenylcyclopentylmethyl)pyrimidine-4-carboxylic acid [2-(tert-butyldimethylsilanyloxy)ethyl](2,2-dimethylpropyl)amide 
• 1616924-66-3 5-benzyloxy-6-hydroxy-2-(1-phenylcyclopentylmethyl)pyrimidine-4-carboxylic acid (2-hydroxyethyl)oxetan-3-ylamide 

Relevant academic research and scientific papers

A first homogeneous gold(III)-catalysed epoxidation of aromatic alkenes

The first example of a homogeneous gold(III)-catalysed epoxidation of aromatic alkenes at room temperature using sodium chlorite as the stoichiometric oxidant in a homogeneous trisolvent system of 2-methoxyethanol/acetonitrile/ water (volume ratio: 1/3/1)

An Efficient, Catalytic Procedure for Epoxide Rearrangement

Exceptionally bulky, oxygenophilic methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (reagent A) can be utilized as an active catalyst for the transformation of various epoxides to carbonyl compounds with high efficiency and selectivity.

Kinetic Resolution of Neopentylic Secondary Alcohols by Cu-H-Catalyzed Enantioselective Silylation with Hydrosilanes

A nonenzymatic kinetic resolution of sterically congested alcohols having a quaternary carbon atom in the β-position is reported. The catalyst system CuCl/NaOtBu/(R,R)-Ph-BPE together with a 3,5-xylyl-substituted tertiary hydrosilane enable enantioselective silylation of the hydroxy group. Several alcohols are obtained with good to excellent selectivity factors, and there are no other known straightforward methods to access these motifs.

Preparation of isoquinazolines: Via metal-free [4 + 2] cycloaddition of ynamides with nitriles

TfOH-mediated [4 + 2] cycloaddition of ynamides with nitriles to construct 1,2-dihydroquinazolines is realized by a direct reaction in moderate to excellent yields (up to 93%) in a stereospecific manner. A rapid and efficient strategy has been employed for the syntheses of alkyl-substituted 1,2-dihydroquinazoline derivatives, and it exhibits good functional group tolerance, has a short reaction time, shows excellent diastereoselectivity, and is a simple and high-yielding reaction.

Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes

The direct reduction of carboxylic acids to aldehydes is a fundamental transformation in organic synthesis. The combination of an air-stable Ni precatalyst, dimethyl dicarbonate as an activator, and silane reductant effects this reduction for a wide variety of substrates, including pharmaceutically relevant structures, in good yields and with no overreduction to alcohols. Moreover, this methodology is scalable, allows access to deuterated aldehydes, and is also compatible with one-pot utilization of the aldehyde products.

Synthesis of α-Arylated Cycloalkanones from Congested Trisubstituted Spiro-epoxides: Application of the House-Meinwald Rearrangement for Ring Expansion

A three-step sequence for the synthesis of α-arylated cyclohexanones and the most challenging cycloheptanones is reported. First, an efficient one-pot synthesis of β,β'-disubstituted benzylidene cycloalkanes (styrenes) using the palladium-catalyzed Barluenga reaction from readily available feedstock chemicals is described. Furthermore, an epoxidation followed by the House-Meinwald rearrangement (HMR) of spiro-epoxides is reported to produce a number of α-arylated cycloalkanones upon ring expansion. Reactions catalyzed by bismuth triflate underwent quasi-exclusively ring expansion for all substrates (electronically poor and rich), with yields ranging from 15% to 95%, thus demonstrating the difficulty of achieving ring enlargement for electron-deficient spiro-epoxides. On the other hand, by means of catalysis with aluminum trichloride, the rearrangement of spiro-epoxides proceeded typically in high yields and with remarkable regioselectivity on a broader substrate scope. In this case, a switch of regioselectivity was achieved for spiro-epoxides with electron-withdrawing substituents which enable the method to be successfully extended to some chemospecific arene shifts and the synthesis of aldehydes bearing a α-quaternary carbon. While the HMR has been extensively studied for smaller ring enlargement, we are pleased to report herein that larger cyclohexanones and cycloheptanones can be obtained efficiently from more sterically demanding trisubstituted spiro-epoxides bearing electron-releasing and electron-neutral arene substituents.

Pinacol Rearrangement and Direct Nucleophilic Substitution of Allylic Alcohols Promoted by Graphene Oxide and Graphene Oxide CO2H

Graphene oxide (GO) and carboxylic acid functionalized GO (GO–CO2H) have been found to efficiently promote the heterogeneous and environmentally friendly pinacol rearrangement of 1,2-diols and the direct nucleophilic substitution of allylic alcohols. In general, high yields and regioselectivities are obtained in both reactions using 20 wt % of catalyst loading and mild reaction conditions.

Br?nsted Acid-Catalyzed Intramolecular Hydroarylation of β-Benzylstyrenes

Using triphenylmethylium tetrakis(pentafluorophenyl)borate as a convenient Br?nsted acid precatalyst, β-(α,α-dimethylbenzyl)styrenes are shown to cyclize efficiently to afford a variety of new indanes that possess a benzylic quaternary center. The geminal dimethyl-containing quaternary center is proposed to be necessary to arm the substrate for cyclization through steric biasing.

Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products

The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.

Synthesizing method of pentoxyverine drug intermediate 1-phenylcyclopentanecarboxylic acid

Provided is a synthesizing method of a pentoxyverine drug intermediate 1-phenylcyclopentanecarboxylic acid. The method comprises the following steps that 230 ml of sodium hydrogen sulfite solution and 0.15 mol of stannous chloride are added into a reaction vessel provided with a stirrer, a thermometer, a reflux condenser and a dropping funnel, the stirring speed is controlled to be 130-160 rpm, and the temperature of the solution is increased to 50-55 DEG C; 0.63 mol of phenylacetaldehyde (2) and 0.71-0.73 mol of 1,4-diaminobutane are slowly added, the temperature of the solution is increased to 60-65 DEG C, and stirring is continuously conducted for 8-9 h for reaction; 230 ml of potassium bromide solution is added, the temperature of the solution is decreased to 10-15 DEG C, oily liquid is dissolved out, the intermediate product is washed with propionitrile 7-9 times, the oily matter is added into 300 ml of cyclohexane solution, 130 ml of potassium bromide solution, 0.23 mol of cuprous chloride and 0.26 mol of potassium sulfite are added, the temperature of the solution is increased to 150-160 DEG C, and refluxing is conducted for 7-8 h; 2 L of sodium chloride solution is added, molecular sieve decoloring is conducted, filtering is conducted while the solution is hot, oxalic acid is added to filtrate to adjust the pH of the filtrate to be 1-2, a white solid is dissolved out, suction filtration is conducted, salt solution washing and toluene washing are conducted, dehydration is conducted through a dehydrating agent, recrystallization is conducted in nitromethane, and the crystal 1-phenylcyclopentanecarboxylic acid is obtained.