40360-71-2

Basic information

• Product Name: anhydrolycorinone
• Synonyms: anhydrolycorinone;4,5-Dihydro-7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-7-one;9,10-(Methylenedioxy)-4,5-dihydro-7H-pyrrolo[3,2,1-de]phenanthridine-7-one;Anhydrolycorin-7-one;Anhydrolycorinon
• CAS NO: 40360-71-2
• Molecular Weight: 0
• Mol File: 40360-71-2.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 524.8°C at 760 mmHg
• Flash Point: 271.2°C
• Appearance: /
• Density: 1.53g/cm³
• Vapor Pressure: 4.18E-11mmHg at 25°C
• Refractive Index: 1.76
• CAS DataBase Reference: anhydrolycorinone(CAS DataBase Reference)
• NIST Chemistry Reference: anhydrolycorinone(40360-71-2)
• EPA Substance Registry System: anhydrolycorinone(40360-71-2)

Safety Data

• Hazardous Substances Data: 40360-71-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H11NO3/c18-16-12-7-14-13(19-8-20-14)6-11(12)10-3-1-2-9-4-5-17(16)15(9)10/h1-3,6-7H,4-5,8H2

Upstream product

• 40360-67-6 1-[(1,3-benzodioxol-5-yl)carbonyl]-2,3-dihydroindole 
• 136582-40-6 (6-Iodo-benzo[1,3]dioxol-5-yl)-(7-iodo-2,3-dihydro-indol-1-yl)-methanone 
• 151692-89-6 1-(6-Ethynyl-1,3-benzodioxol-5-ylcarbonyl)azacyclopent-2-ene 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 6391-78-2 (1S,2S,3a⁽¹⁾S,12bS)-7-oxo-2,3a⁽¹⁾,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrole[3,2,1-de]phenanthridine-1,2-diyl diacetate 
• 58700-93-9 (1S,2S,3a⁽¹⁾S,12bS)-1,2-dihydroxy-3a⁽¹⁾,4,5,12b-tetrahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-7(2H)-one 
• 476-28-8 lycorine 
• 2492-05-9 1,2-diacetoxylycorine 
• 61441-09-6 methyl 6-bromo-1,3-benzodioxole-5-carboxylate 
• 62813-85-8 7-bromo-2,3-dihydroindole 
• 40851-64-7 2-(2-(azidomethyl)phenyl)acetic acid 
• 4385-35-7 isochroman-3-one 
• 1394134-42-9 1-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)indolin-2-one 
• 636608-02-1 1-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-2,3-dihydroindole 

Downstream Products

• 88660-12-2 pratorimine 
• 61221-42-9 anhydrolycorinium chloride 
• 52886-06-3 hippadine 

Relevant articles and documents

Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole

A convergent total synthesis of anhydrolycorinone is detailed, enlisting sequential intramolecular Diels-Alder reactions of a suitably substituted 2-amino-1,3,4-oxadiazole defining a novel oxadiazole → furan → benzene Diels-Alder strategy.

Electrochemical Total Synthesis of Pyrrolophenanthridone Alkaloids: Controlling the Anodically Initiated Electron Transfer Process

Electrochemical intramolecular C(sp2)-H cross-coupling and dehydrogenative indole synthesis were developed. Both reactions were initiated by anodic oxidation of the same electron-rich indoline moiety, but the product selectivity was controlled

A Pd-catalyzed, boron ester-mediated, reductive cross-coupling of two aryl halides to synthesize tricyclic biaryls

Tricyclic biaryls are important scaffold structures in many natural products and lead compounds in drug discovery. The formation of a biaryl unit is often the key step for the synthesis of tricyclic biaryls. Despite significant progress toward the synthesis of biaryl compounds in recent years, the direct cross-coupling of two different aryl halides is still challenging and robust methods are lacking. Herein we report a direct cross-coupling of two different aryl halides in the presence of a palladium catalyst and boron ester, which provides a new and useful complementary method to synthesize tricyclic biaryls.

Expeditious approach to pyrrolophenanthridones, phenanthridines, and benzo[ c ]phenanthridines via organocatalytic direct biaryl-coupling promoted by potassium tert -butoxide

A methodology involving a "transition metal-free" intramolecular biaryl-coupling of o-halo-N-arylbenzylamines has been developed in the presence of potassium tert-butoxide and an organic molecule as catalyst. The reaction appears to proceed through KOtBu-promoted intramolecular homolytic aromatic substitution (HAS). Interestingly, this biaryl coupling also works in the presence of potassium tert-butoxide as sole promoter. On extending our approach further, we found that N-acyl 2-bromo-N-arylbenzylamines undergo a one-pot N-deprotection/biaryl coupling followed by oxidation, thus offering an expeditious route to the phenanthridine and benzo[c]phenanthridine skeletons. The strategy has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), 5,6-dihydrobicolorine (2d), trispheridine (2b), and benzo[c]phenanthridines alkaloids dihydronitidine (3b), dihydrochelerythidine (3d), dihydroavicine (3f), nornitidine (3h), and norchelerythrine (3j).