5588-52-3

Basic information

• Product Name: (6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one(SALTDATA: FREE)
• Synonyms: (6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one(SALTDATA: FREE);(6S,11aR,11bS)-6,8,9,10,11,11a-hexahydro-2H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2-one
• CAS NO: 5588-52-3
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.2637
• Mol File: 5588-52-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 463.3°Cat760mmHg
• Flash Point: 234°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 9.2E-09mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: (6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one(SALTDATA: FREE)(CAS DataBase Reference)
• NIST Chemistry Reference: (6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one(SALTDATA: FREE)(5588-52-3)
• EPA Substance Registry System: (6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one(SALTDATA: FREE)(5588-52-3)

Safety Data

• Hazardous Substances Data: 5588-52-3(Hazardous Substances Data)

Usage

General Description

The chemical "(6S,11aR,11bS)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one" is a complex organic compound with a unique structure. It is commonly known by its chemical abstracts service registry number (SALTDATA: FREE) and belongs to the class of furo[2,3-c]pyrido[1,2-a]azepin-2(6H)-one compounds. This chemical exhibits potential pharmacological activity and may be used in the development of pharmaceutical drugs or as a research tool in the field of medicinal chemistry. Further studies and research are needed to understand the full potential and applications of this chemical compound.

InChI:InChI=1/C12H13ClN4O4/c13-11(12(18)16-5-7-21-8-6-16)15-14-9-3-1-2-4-10(9)17(19)20/h1-4,14H,5-8H2

Upstream product

• 14140-69-3 (RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine 
• 651738-07-7 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene 
• 651738-04-4 tert-butyl (2R)-2-[(7aS)-2(6H)-oxo-7,7a-dihydro-7a-benzofuranyl]piperidine-1-carboxylate 
• 708260-76-8 tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate 
• 651737-95-0 1-tert-butoxycarbonyl-2(R)-[4'(Z)-heptenoyl]piperidine 
• 651738-03-3 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-9-oxabicyclo[4.3.0]nona-4,6-diene 
• 651737-98-3 1(S)-[(2'R)-N-tert-butoxycarbonylpiperidinyl]-1-ethynyl-4(Z)-hepten-1-ol 
• 651737-99-4 1-tert-butoxycarbonyl-2(R)-[1'(S)-allyloxy-1'-ethynyl-4'(Z)-heptenyl]piperidine 
• 651737-96-1 1(S)-[(2''R)-N-tert-butoxycarbonylpiperidinyl]-1-(2'-trimethylsilylethynyl)-4(Z)-hepten-1-ol 
• 14140-68-2 (RS)-1-formyl-2-((SR)-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine 
• 5890-59-5 (RS)-7a-(SR)-piperidin-2-yl-7,7a-dihydro-6H-benzofuran-2-one 
• 1126784-60-8 (1'S,3'S,8a'R)-3'-((Z)-2-iodovinyl)-3',5',6',7',8',8a'-hexahydro-2'H,5H-spiro[furan-2,1'-indolizin]-5-one 

Downstream Products

• 42555-40-8 1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate 
• 3909-79-3 Tetrahydrosecurinin 
• 3909-79-3 Tetrahydrosecurinin 
• 1085244-06-9 (2β,15α)-14,15-dihydro-15-(4-phenylpiperazin-1-yl)securinan-11-one 
• 1085244-08-1 (2β,15α)-14,15-dihydro-15-[4-(4-methoxyphenyl)piperazin-1-yl]securinan-11-one 

Relevant articles and documents

Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine

(Chemical Equation Presented) The most representative securinega alkaloids have been synthesized through a new strategy involving the palladium-catalyzed enantioselective allylation of a cyclic imide, a vinylogous Mannich reaction, and a ring-closing meta

First Diastereoselective Chiral Synthesis of (-)-Securinine

(Equation presented) A diastereoselective total synthesis of securinine in optically pure form was achieved by employing ring-closing metathesis of the corresponding dienyne compound as a key step.

Kinetics and mechanism of the alkaline hydrolysis of securinine

The hydroxide ion-catalyzed hydrolysis of securinine involves the ring opening of the lactone moiety. The rate of hydrolysis is insensitive to the ionic strength. The observed pseudo-first-order rate constants reveal a decrease of approximately 4-fold due to the increase in the MeCN content from 4 to 50% (v/v) in mixed aqueous solvent. The temperature dependence of the rate of hydrolysis follows the Eyring equation, which yields ΔH* and ΔS* as 11.0 kcal mol-1 and -34.5 cal deg-1 mol-1, respectively. The hydroxy carboxylate product of the alkaline hydrolysis of securinine is shown to undergo cyclization in acidic medium to yield securinine. The observed pseudo-first-order rate constants for cyclization increase linearly with an increase in [H+]. The change in the content of MeCN from 3.8 to 47.2% (v/v) in mixed aqueous solvents does not show an effect on the rate of the cyclization reaction. The most plausible mechanisms for alkaline hydrolysis and acid cyclization reactions are also discussed.