Securinine

Base Information

• Chemical Name: Securinine
• CAS No.: 5610-40-2
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• European Community (EC) Number: 694-738-6
• NSC Number: 758972
• UNII: G4VS580P5E
• DSSTox Substance ID: DTXSID7045944
• Wikipedia: Securinine
• Wikidata: Q4413415
• NCI Thesaurus Code: C81359
• ChEMBL ID: CHEMBL303062
• Mol file: 5610-40-2.mol

Synonyms:allonorsecurinine;allosecurinine;securinan-11-one;securinine;securinine methiodide;securinine nitrate

Chemical Property of Securinine

Chemical Property:

• Vapor Pressure: 1.32E-08mmHg at 25°C
• Melting Point: 140-1420C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 459 ºC at 760 mmHg
• PKA: 8.29±0.20(Predicted)
• Flash Point: 197 ºC
• PSA: 29.54000
• Density: 1.3 g/cm³
• LogP: 1.34290
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥25mg/mL
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 426

Purity/Quality:

98%,99%, ^*data from raw suppliers

Securinine ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn
• Statements: 23/24/25-22
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2C(C1)C34CC2C=CC3=CC(=O)O4
• Isomeric SMILES: C1CCN2[C@H](C1)[C@]34C[C@H]2C=CC3=CC(=O)O4
• Description: A constituent of the leaves of Securinega suffructicosa Rehd., the base also occurs in Phyllanthus disco ides. It is obtained as yellow crystals and is strongly laevorotatory having [α]20D - 1106°(CHC13), [α]30D - 1106°(CHC13) and[α]20D - 1042° (c 1.0, EtOH). The alkaloid yields a crystalline methiodide, m.p. 235-6°C.
• Uses: Extracted from leaves and roots of Securinega suffruticosa Rehder. The most widely studied of these alkaloids, Securinine, is a specific GABA receptor antagonist and has been found to have significant in vivo CNS activity. GABAA receptor blocker, CNS stimulant

Technology Process of Securinine

There total 16 articles about Securinine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene (651738-07-7) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene; With trifluoroacetic acid; at 20 ℃; for 0.25h;

With potassium carbonate; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/ol0361251

Reference yield: 82.0%

(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 (1126784-60-8) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutylammomium bromide; sodium acetate; In N,N-dimethyl acetamide; at 100 ℃; for 12h;

DOI:10.1039/b816576a

Reference yield:

tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate (708260-76-8) → (-)-securinine (884-68-4,1857-30-3,5588-52-3,5610-40-2,6704-68-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 78 percent / PdCl₂(PPh₃)2; tetrabutylammonium bromide; PPh₃ / Na₂CO₃ / dimethylformamide / 90 °C

2.1: 64 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 0.75 h / Heating

3.1: trifluoroacetic acid / CHCl₃ / 20 °C

3.2: 53 percent / K₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / sonication

With bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; tetrabutylammomium bromide; triphenylphosphine; trifluoroacetic acid; dibenzoyl peroxide; sodium carbonate; In tetrachloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Heck reaction;

DOI:10.1021/ol049455+

upstream raw materials:

(RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine

1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene

tert-butyl (2R)-2-[(7aS)-2(6H)-oxo-7,7a-dihydro-7a-benzofuranyl]piperidine-1-carboxylate

tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate

Refernces

• 1、 Gonzalez-Galvez, David,Garcia-Garcia, Elena,Alibes, Ramon,Bayon, Pau,De March, Pedro,Figueredo, Marta,Font, Josep. "Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine". experimental part. p. 6199 - 6211. Retrieved 2010/01/06.
• 2、 Alibes, Ramon,Ballbe, Marta,Busque, Felix,De March, Pedro,Elias, Laia,Figueredo, Marta,Font, Josep. "A new general access to either type of securinega alkaloids: Synthesis of securinine and (-)-allonorsecurinine". . p. 1813 - 1816. Retrieved 2007/10/03.