911107-22-7

Usage

Uses

Used in Organic Synthesis:
(2R)-2-Phenyl-2H-chromene-3-carboxaldehyde is utilized as a versatile intermediate in organic synthesis for the preparation of a wide range of organic compounds. Its carboxaldehyde functional group allows for various chemical reactions, facilitating the creation of complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (2R)-2-Phenyl-2H-chromene-3-carboxaldehyde is employed as a key component in the development of new drugs. Its unique structural features and reactivity make it a promising candidate for the synthesis of bioactive molecules with potential therapeutic applications.
Used in Agrochemical Industry:
(2R)-2-Phenyl-2H-chromene-3-carboxaldehyde also finds application in the agrochemical industry, where it is used in the synthesis of novel agrochemicals. Its potential to be incorporated into molecules with biological activity makes it a valuable resource for developing new pesticides or other agrochemical products.
Used in Chemical Research:
(2R)-2-Phenyl-2H-chromene-3-carboxaldehyde is also used in academic and industrial research settings as a subject of study for understanding various chemical reactions and mechanisms. Its unique properties and reactivity can provide insights into new areas of chemical science and technology.

InChI:InChI=1/C16H12O2/c17-11-14-10-13-8-4-5-9-15(13)18-16(14)12-6-2-1-3-7-12/h1-11,16H/t16-/m1/s1

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 104-55-2 3-phenyl-propenal 
• 104-54-1 3-Phenylpropenol 

Relevant academic research and scientific papers

One-pot approach to chiral chromenes via enantioselective organocatalytic domino oxa-Michael-aldol reaction

A highly enantioselective (S)-diphenylpyrrolinol triethylsilyl ether promoted tandem oxa-Michael-aldol reaction of α,β-unsaturated aldehydes with salicylaldehydes has been developed; the method affords one-pot access to chiral and synthetically useful chr

Organocatalytic synthesis of chiral benzopyrans

Benzopyrans, or chromenes, are widespread in nature and are considered to be a privileged scaffold in medicinal chemistry. Herein, we report the first organocatalyzed asymmetric synthesis of chiral benzopyrans. The benzopyran unit is constructed through a

Catalytic enantioselective domino oxa-michael/aldol condensations: Asymmetric synthesis of benzopyran derivatives

The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and α,β-unsaturated aldeh

Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC-Catalyzed Kinetic Resolution

An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining step of the reaction is the formation of the Breslow intermediate, while the selectivity determining step occurs later in the mechanism. The presented methodology enables rapid synthesis of complex structures in a single step.

A novel pyrazoline-based fluorescent probe for Cu2+ in aqueous solution and imaging in live cell

In this study, a new pyrazoline derivate (1-acetyl-3- (2-hydroxy-1-naphthyl)-5-(2-phenyl-2H-chromene)-2-pyrazoline, N) is described as fluorescent probe for fluorometric detection of Cu2+. This fluorescence of probe has a high selectivity only toward Cu2+ ion in the other metal ions. It is remarkably observed that the fluorescence intensity of N decreased in the presence of Cu2+ ions with a strong capability to resist perturbations. The Limit of detection (LOD) value is calculated as 8.85 × 10?7 M for Cu2+ while the complexation constant is calculated as 3.14 × 105 M?2 via fluorescence measurements. The interaction between of N and Cu2+ is reversible after adding PPi. The optimized calculation of the probe for Cu2+ is confirmed by TD-DFT calculations. N-Cu2+ is successfully applied in the intracellular imaging in living PK-21cells that will have a great chance for wide application.

Design, one-pot synthesis, molecular docking study, and antibacterial evaluation of novel 2H-chromene based imidazo[1,2-a]pyridine derivatives as potent peptide deformylase inhibitors

An efficient, environmentally friendly, one-pot three-component synthesis of a series of 2H-chromene-based imidazo[1,2-a]pyridines had been designed and were synthesized. This protocol was developed by the reaction of substituted 2H-chromene aldehydes and

Enantioselective organocatalytic synthesis of the chiral chromenes by domino oxa-Michael-aldol reaction

The proline based chiral organocatalyst has been found to be an efficient catalyst for the facile synthesis of substituted 2-aryl-2H-chromenes-3-carbaldehyde. We envisioned that the iminium interaction between chiral amino catalysts and α,β-unsaturated ca

Design and synthesis of (Z/E)-2-phenyl/H-3-styryl-2H-chromene derivatives as antimicrotubule agents

Abstract: Two new series of compounds (Z?/?E)-2-phenyl/H-3-Styryl-2H-Chromenes 9(a-r) and 10(a-s) were synthesized and evaluated in vitro cytotoxic activities against four cancer cell lines. One compound, (Z)-8-ethoxy-3-(4-methoxystyryl)-2-phenyl-2H-chrom

Diastereoselective synthesis of novel spiro indanone fused pyrano[3,2-: c] chromene derivatives following hetero-Diels-Alder reaction and in vitro anticancer studies

The development of concise methods for the synthesis of small functionalised spirocyclic molecules is important in the search of new bioactive molecules. To contribute this, here we represent a diastereoselective oxa-hetero-Diels-Alder reaction for the synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives and studied their in vitro anticancer activities. Using previously less explored cyclic ketone i.e. indane-1,3-dione and 3-vinyl-2H-chromene derivatives, we obtained novel spiro-heterocyclic frameworks at the interphase between "drug-like" molecules and natural products. Various spiro indanone fused pyrano[3,2-c]chromene derivatives were synthesized regiospecifically bearing a quaternary stereocenter in high yields (up to 85%) with excellent diastereoselectivity in toluene using 4 ? MS as additive under reflux condition at 120 °C. In vitro cytotoxic studies of these compounds against MCF-7 (breast cancer), HCT-116 (colon cancer), H-357 (oral cancer), MD-MB-231(Breast cancer) cell lines were evaluated by MTT {3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide} assay in vitro. The screening results revealed that many of the compounds are showing moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed potent inhibitory activities in comparison to the commercial anticancer drug 5-fluorouracil (5-FU). Among the series, compound 3′c showed most potent cytotoxicity (15.0-27.5 μM) in three cancer cell lines (MCF-7, HCT-116 and MD-MB-231).

A chromene pyrazoline derivatives fluorescent probe for Zn2+ detection in aqueous solution and living cells

A new chromene pyrazoline derivatives fluorescent probe L was designed and synthesized. The probe L appears in a 55-fold fluorescence enhancement after 5 equiv. Zn2+ was added, and it also exhibits high sensitivity and selectivity for response