6704-68-3

Usage

Uses

1. Used in Pharmaceutical Industry:
Virosecurinine is used as a pharmaceutical compound for its potential therapeutic applications. The expression is: virosecurinine is used as a pharmaceutical compound for its potential therapeutic applications.
2. Used in Chemical Research:
Virosecurinine is used as a research chemical for studying its properties, structure, and potential interactions with other compounds. The expression is: virosecurinine is used as a research chemical for studying its properties, structure, and potential interactions with other compounds.
3. Used in Drug Development:
Virosecurinine may be used as a lead compound in the development of new drugs, particularly those targeting specific diseases or conditions. The expression is: virosecurinine is used as a lead compound in drug development for its potential therapeutic applications.

References

Nakano, Yang, Terao., Chern. & Ind., 1651 (1962) Nakano, Yang, Terao., ibid, 1034 (1963) Nakano, Yang, Terao.,J. Org. Chern., 28,2619 (1963) Nakano, Yang, Terao., Tetrahedron, 19,609 (1963) Saito et aI., Chern. & Ind., 689 (1963) Nakano et aI., ibid, 1763 (1963)

InChI:InChI=1/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13?/m0/s1

Upstream product

• 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 
• 651738-07-7 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene 
• 111-29-5 1 ,5-pentanediol 
• 114642-97-6 5-azido-1-pentanal 
• 170220-11-8 5-azido-1-pentanol 
• 34626-51-2 5-bromopentan-1-ol 
• 15848-22-3 5-bromo-1-pentanyl acetate 
• 5890-59-5 (RS)-7a-(SR)-piperidin-2-yl-7,7a-dihydro-6H-benzofuran-2-one 
• 14140-68-2 (RS)-1-formyl-2-((SR)-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine 
• 14140-69-3 (RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine 
• 651737-96-1 1(S)-[(2''R)-N-tert-butoxycarbonylpiperidinyl]-1-(2'-trimethylsilylethynyl)-4(Z)-hepten-1-ol 
• 651737-99-4 1-tert-butoxycarbonyl-2(R)-[1'(S)-allyloxy-1'-ethynyl-4'(Z)-heptenyl]piperidine 
• 651737-98-3 1(S)-[(2'R)-N-tert-butoxycarbonylpiperidinyl]-1-ethynyl-4(Z)-hepten-1-ol 
• 651738-03-3 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-9-oxabicyclo[4.3.0]nona-4,6-diene 

Downstream Products

• 42555-40-8 1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate 
• 3909-79-3 Tetrahydrosecurinin 

Relevant academic research and scientific papers

Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (?)-Episecurinol A

The so-called Securinega alkaloids constitute a class of tetracyclic biologically active specialised metabolites isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (?)-episecurinol A.

The asymmetric total synthesis of (-)-securinine

The alkaloid (-)-securinine was synthesized in 18 steps and 16% overall yield from trans-4-hydroxy-l-proline. The Royal Society of Chemistry.

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.

A new general access to either type of securinega alkaloids: Synthesis of securinine and (-)-allonorsecurinine

Matrix presented. The syntheses of securinine and (-)-allonorsecurinine have been achieved starting from easily available α-amino acid derivatives and using as key steps a RCM and a Heck reaction for the formation of rings D and C, respectively.

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.