58336-35-9

Basic information

• Product Name: 2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN
• Synonyms: 2,3,6,7-tetrahydro-1h,5h,11h-(1)benzopyrano(6,7,8-ij)-quinolizin-11-one;5h,11h-(1)benzopyrano(6,7,8-ij)quinolizin-11-one,2,3,6,7-tetrahydro-1;5h,11h-[1]benzopyrano[6,7,8-ij]quinolizin-11-one,2,3,6,7-tetrahydro-1;c6h;excitonld490;ld490;2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN;COUMARIN 540H
• CAS NO: 58336-35-9
• Molecular Formula: C₁₅H₁₅NO₂
• Molecular Weight: 241.29
• EINECS: 261-213-4
• Mol File: 58336-35-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 128.0 to 132.0 °C
• Boiling Point: 486.3°C at 760 mmHg
• Flash Point: 201°C
• Appearance: /
• Density: 1.32g/cm³
• Vapor Pressure: 1.31E-09mmHg at 25°C
• Refractive Index: 1.665
• PKA: 5.63±0.20(Predicted)
• CAS DataBase Reference: 2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN(58336-35-9)
• EPA Substance Registry System: 2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN(58336-35-9)

Safety Data

• WGK Germany: 3
• RTECS: DJ3310000
• Hazardous Substances Data: 58336-35-9(Hazardous Substances Data)

Usage

General Description

2,3,5,6-1H,4H-tetrahydroquinolizino[9,9a,1-gh]coumarin is a complex chemical compound that belongs to the coumarin family. It is a fused polycyclic compound that contains a coumarin core and a tetrahydroquinoline moiety. This chemical exhibits various biological and pharmacological activities, such as anti-inflammatory, antitumor, and antimicrobial properties. Its unique structure and functional groups make it an interesting target for synthetic chemists and medicinal chemists for the development of new pharmaceutical agents. Additionally, its molecular conformation and interactions with biological targets are also of interest to researchers in the fields of biochemistry and pharmacology.

InChI:InChI=1/C15H15NO2/c17-13-6-5-11-9-10-3-1-7-16-8-2-4-12(14(10)16)15(11)18-13/h5-6,9H,1-4,7-8H2

Upstream product

• 63149-33-7 9-formyl-8-hydroxyjulolidine 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 591-27-5 m-Hydroxyaniline 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 536-90-3 m-Anisidine 
• 55804-66-5 ethyl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f ]-pyrido[3,2,1-ij]quinoline-10-carboxylate 
• 105-53-3 diethyl malonate 
• 213481-01-7 9-hydroxy-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one 
• 41175-50-2 8-hydroxyjulolidine 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 142730-52-7 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde 
• 521306-75-2 2-[(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-9-yl)-phenyl-phosphanyl]-benzoic acid methyl ester 

Relevant articles and documents

Development of a coumarin-based fluorescent probe for hydrogen peroxide based on the Payne/Dakin tandem reaction

Hydrogen peroxide (H2O2) is associated with many physiological and pathological processes in biological systems. Here, we report 7-diethylamino-3-formyl-coumarin (Cou-CHO) as a turn-on fluorescent probe for H2O2. The proposed probe employs a tandem Payne/Dakin reaction to convert the electron-withdrawing aldehyde to the electron-donating hydroxyl group, thus hindering the formation of twisted intramolecular charge transfer (TICT) state of 7-diethylaminocoumarin, and thereby resulting in a fluorescence turn-on response. Cou-CHO features high specificity, excellent sensitivity and fast response toward H2O2. In particular, Cou-CHO enables the direct visualization of basal and endogenously produced H2O2 in living cells. The results demonstrate that the tandem Payne/Dakin reaction can provide a new choice to develop H2O2-selective probes.

Near-infrared fluorescent probe for simultaneously detecting DNA and RNA under double channels as well as preparation method and application of the near-infrared fluorescent probe

The invention discloses a fluorescent probe for simultaneously detecting DNA and RNA in cells under double channels as well as a preparation method and application of the fluorescent probe. The structure of the fluorescent probe is shown as a formula (I) or (II), wherein the Ar is an aromatic ring or an aromatic heterocyclic ring; the R1 and R2 are respectively and independently hydrogen, N-piperazine, N-methyl piperazine, -NH(CH2)nR3 and -NR3R4; the n is any integer from 1 to 5, and R3 and R4 are respectively and independently hydrogen, C1-C5 alkyl or C1-C5 haloalkyl; the A- is halide ions orp-toluenesulfonic acid ions. The fluorescent probe disclosed by the invention can be used for simultaneously detecting DNA and RNA in vitro and in cells under double channels; meanwhile, the fluorescent probe has the characteristics of rapid synthesis, near-infrared emission wavelength, good light stability, high detection sensitivity and the like, and is convenient to popularize and apply.

Synthesis of 7-Azido-3-Formylcoumarin – A Key Precursor in Bioorthogonally Applicable Fluorogenic Dye Synthesis

Coumarins represent an important group of natural products and a common part of various drugs and fluorescent dyestuffs. Herein, we present the synthesis of a coumarin that can serve as a key starting material in the design and synthesis of bioorthogonally applicable fluorogenic dyes. The synthesis of 7-azido-3-formylcoumarin started from 7-diallylaminocoumarin. This allyl protected aminocoumarin is otherwise hard to obtain by conventional methods but was conveniently accessed in good yields by a sequential, Wittig-reaction–UV isomerization process. This sequential approach was studied in more details and applied for the synthesis of a series of substituted coumarins even in one-pot.