1361253-97-5

Basic information

• Product Name: [2-(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester
• Synonyms: [2-(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester
• CAS NO: 1361253-97-5
• Molecular Weight: 418.492
• Mol File: 1361253-97-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [2-(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester(1361253-97-5)
• EPA Substance Registry System: [2-(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester(1361253-97-5)

Safety Data

• Hazardous Substances Data: 1361253-97-5(Hazardous Substances Data)

Upstream product

• 536-90-3 m-Anisidine 
• 2304-94-1 3-(benzyloxycarbonylamino)propanoic acid 
• 41175-50-2 8-hydroxyjulolidine 
• 99017-63-7 methyl 5-<(benzyloxycarbonyl)amino>-3-oxopentanoate 
• 20717-86-6 triisopropoxytitanium(IV) chloride 

Downstream Products

• 1361254-15-0 [2-(9-iodo-10-oxo-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester 
• 1361254-17-2 [2-(10-oxo-9-phenylethynyl-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester 
• 1361254-19-4 [2-(9-(4-chlorophenyl)-10-oxo-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-8-yl)ethyl]carbamic acid benzyl ester 

Relevant articles and documents

Pictet-Spengler condensations using 4-(2-aminoethyl)coumarins

Androgen-deprivation therapy (ADT) is only a palliative measure, and prostate cancer invariably recurs in a lethal, castration-resistant form (CRPC). Prostate cancer resists ADT by metabolizing weak, adrenal androgens to growth-promoting 5α-dihydrotestosterone (DHT), the preferred ligand for the androgen receptor (AR). Developing small-molecule inhibitors for the final steps in androgen metabolic pathways that utilize 17-oxidoreductases required probes that possess fluorescent groups at C-3 and intact, naturally occurring functionality at C-17. Application of the Pictet-Spengler condensation to substituted 4-(2-aminoethyl)coumarins and 5α-androstane-3-ones furnished spirocyclic, fluorescent androgens at the desired C-3 position. Condensations required the presence of activating C-7 amino or N,N-dialkylamino groups in the 4-(2-aminoethyl)coumarin component of these condensation reactions. Successful Pictet-Spengler condensation, for example, of DHT with 9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one led to a spirocyclic androgen, (3R,5S,10S,13S,17S)-17-hydroxy-10,13-dimethyl-1,2,2′,3′,4,5,6,7,8,8′,9,9′,10,11,12,12′,13,13′,14,15,16,17-docosahydro-7′H,11′H-spiro-[cyclopenta[a]phenanthrene-3,4′-pyrido[3,2,1-ij]pyrido[4′,3′:4,5]pyrano[2,3-f]quinolin]-5′(1′H)-one. Computational modeling supported the surrogacy of the C-3 fluorescent DHT analog as a tool to study 17-oxidoreductases for intracrine, androgen metabolism. This journal is

A mild titanium-catalyzed synthesis of functionalized amino coumarins as fluorescence labels

In contrast to Bronsted and other Lewis acids ClTi(OiPr)3 is especially suited to catalyze the formation of amino-substituted coumarins from aminophenols and functionalized β-oxo esters in a Pechmann condensation. This straightforward protocol allows the synthesis of fluorescence labels and false fluorescent neurotransmitters.