58647-67-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-2-(4-Methoxybenzylidene)cyclopentanone is used as an intermediate in the synthesis of pharmaceuticals due to its unique chemical structure and reactivity. It plays a crucial role in the development of new drugs and medicines.
Used in Fragrance and Flavor Industry:
In the fragrance and flavor industry, (E)-2-(4-Methoxybenzylidene)cyclopentanone is used as an ingredient to impart its characteristic sweet, floral odor to products, enhancing the sensory experience for consumers.
Used in the Food and Beverage Industry:
(E)-2-(4-Methoxybenzylidene)cyclopentanone is also utilized as a flavor and fragrance ingredient in the food and beverage sector, where it adds to the overall taste and aroma profile of various products.
Used in Material Development:
(E)-2-(4-Methoxybenzylidene)cyclopentanone has potential applications in the development of new materials, thanks to its chemical properties and reactivity, which can be harnessed to create innovative and improved materials for various uses.
Used as a Reagent in Organic Chemistry:
(E)-2-(4-Methoxybenzylidene)cyclopentanone serves as a reagent in organic chemistry reactions, facilitating specific transformations and syntheses that are essential in the creation of complex organic molecules.

InChI:InChI=1/C13H14O2/c1-15-12-7-5-10(6-8-12)9-11-3-2-4-13(11)14/h5-9H,2-4H2,1H3

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 120-92-3 cyclopentanone 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 1082283-00-8 C₁₇H₂₁NO₂ 

Downstream Products

• 5447-53-0 2,5-bis-(4-methoxy-benzylidene)-cyclopentanone 
• 120517-49-9 4-(4-methoxyphenyl)-2-sulfanylidene-1H,2H,5H,6H,7H-cyclopenta[b]pyridine-3-carbonitrile 
• 302554-32-1 2-[3-cyano-4-(4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindin-2-ylsulfanyl]-acetamide 
• 302554-62-7 4-chloro-10-(p-methoxyphenyl)cyclopenta[5',6']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine 
• 302554-43-4 3-amino-4-(p-methoxyphenyl)-cyclopenta[e]thieno[2,3-b]pyridine-2-carboxylic acid 
• 302554-63-8 10-(p-methoxyphenyl)cyclopenta[5',6']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-4(3H)-thione 
• 302554-52-5 10-(p-methoxyphenyl)cyclopenta[5',6']pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-one 
• 302554-36-5 3-amino-4-(4-methoxy-phenyl)-6,7-dihydro-5H-1-thia-8-aza-s-indacene-2-carboxylic acid amide 
• 302554-44-5 2-methyl-10-(p-methoxyphenyl)-cyclopenta[5',6']pyrido[3',2':4,5]thieno[3,2-d][1,3]oxazin-4-one 
• 302554-38-7 [3-cyano-4-(4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindin-2-ylsulfanyl]-acetic acid hydrazide 
• 302554-30-9 [3-cyano-4-(4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindin-2-ylsulfanyl]-acetic acid ethyl ester 
• 302554-34-3 3-amino-4-(4-methoxy-phenyl)-6,7-dihydro-5H-1-thia-8-aza-s-indacene-2-carboxylic acid ethyl ester 
• 302554-72-9 3-amino-4-(p-methoxyphenyl)-cyclopenta[e]thieno[2,3-b]pyridine-2-carbonylazide 
• 302554-45-6 4-(4-methoxy-phenyl)-6-methyl-2,3-dihydro-1H,7H-9-thia-5,7,10-triaza-cyclopenta[b]fluoren-8-one 

Relevant academic research and scientific papers

Metal- and Solvent-Free Transesterification and Aldol Condensation Reactions by a Homogenous Recyclable Basic Ionic Liquid Based on the 1,3,5-Triazine Framework

A new recyclable basic ionic liquid was introduced as an efficient catalyst for aldol condensation and transesterification reactions under environmentally friendly conditions. The catalyst was prepared based on methyl imidazolium moieties bearing hydroxide counter anions via the Hofmann elimination on a 1,3,5-triazine framework. The ionic liquid with two functionalities including anion stabilizer and high basicity, was used as an efficient catalyst for aldol condensation as well as transesterification reaction of a variety of alkyl benzoates. All reactions were performed in the absence of any external reagent, co-catalyst, or solvent, in line with environmental protection. The kinetics isotope effect (KIE) was conducted for the transesterification reaction to elucidate the mechanism and rate determining step (RDS). It worth noted that, the homogeneous catalyst could be recycled from the reaction mixture and reused for several consecutive runs with insignificant drop of basicity and conversion.

Asymmetric bio- and chemoreduction of 2-benzylidenecyclopentanone derivatives

Highly efficient asymmetric reduction of 2-benzylidenecyclopentanone derivatives to give the respective exocyclic allylic alcohols in ee's up to 96% was performed with chiral oxazaborolidine-based catalysts. Complete enantioselectivity furnishing (S)-conf

Ultrasound mediation for efficient synthesis of monoarylidene derivatives of homo- and heterocyclic ketones

Ultrasonic irradiation was efficiently used for high yield synthesis of monoarylidene derivatives of cyclic systems directly from the reaction of ketone with various aldehydes under solvent-free conditions. Reactions took place rapidly in the presence of catalytic amounts of pyrrolidine, while no significant formation of the undesired bis by-products was observed. Moreover, the procedure was applicable to both homo- and heterocyclic ketones.

2-METHYLENE-5-SUBSTITUTED-METHYLENECYCLOPENTANONE DERIVATIVES AND USE THEREOF

The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.

An efficient procedure for the synthesis of α,β-unsaturated ketones and its application to heterocyclic systems

An efficient and room-temperature procedure is developed for high yield synthesis of novel α,β-unsaturated derivatives of thiopyran 3 directly from ketone 1 and various aldehydes in the presence of catalytic quantities of TMSNMe2 and MgBr2OEt2 under solvent-free conditions. The main advantage of the procedure is that the formation of the undesired bis by-products is minimized. In addition, the procedure is applicable to other enolizable carbocyclic and acyclic ketones. Georg Thieme Verlag Stuttgart. New York.

2-METHYLENE-5-SUBSTITUTED METHYLENE CYCLOPENTANONE DERIVATIVES AND USE THEREOF

The invention relates to 2-methylene-5-substituted-methylenecyclopentanone derivatives of formula I, and the use thereof. The derivatives of formula I as active components are useful for preparing a medicine for the treatment and/or prevention of cancer diseases such as breast cancer, lung cancer, colon cancer, rectal cancer, stomach cancer, prostate cancer, bladder cancer, uterus cancer, pancreatic cancer and ovary cancer. The active compounds of the invention may be used as an anticancer drug alone or used in combination with one or more other antitumor drugs. A combined therapy can be carried out by administrating each therapeutic component concurrently, subsequently or separately.

Conjugate addition of allyl stannanes with concomitant triflation

A new method for the conjugate addition of allyltributylstannane with concomitant triflation is described. This reaction works with functionalized enones, enals, enoates, and vinylogous esters. The resulting vinyl triflates can be used for intramolecular Heck reactions to afford the products of 5-exo-trig cyclization.

Quinoline synthesis: Scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes

Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6-substituted-2,3-dihydro-1H-cyclopenta[b] quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactions of meta-substituted precursors are highly regioselective, with alkyl substituents leading to 5-substituted 2,3-dihydro-1H-cyclopenta[b]quinolines and more strongly electron-donating substituents generally resulting in 7-substituted products. 2-Furylmethylene and 2-thienylmethylene analogues yield annulated furo- and thieno-[2,3e]pyridines respectively. Sequential E- to Z-benzylidene group isomerisation and six π-electron cyclisation steps result in formation of a short-lived dihydroquinoline intermediate which spontaneously aromatises by elimination of an alcohol or acetic acid. For 2-benzylidenecyclopentanone O-allyloxime, singlet excited states are involved in both steps. The Royal Society of Chemistry 2007.