(-)-Anabasine

Base Information

• Chemical Name: (-)-Anabasine
• CAS No.: 494-52-0
• Molecular Formula: C10H14 N2
• Molecular Weight: 162.235
• Hs Code.: 29333990
• European Community (EC) Number: 207-791-3
• NSC Number: 87504
• UNII: LMS11II2LO
• DSSTox Substance ID: DTXSID9041607
• Nikkaji Number: J3.284K
• Wikipedia: Anabasine
• Wikidata: Q419308
• NCI Thesaurus Code: C124073
• Metabolomics Workbench ID: 52796
• ChEMBL ID: CHEMBL1526229
• Mol file: 494-52-0.mol

Synonyms:Anabasine;Neonicotine

Chemical Property of (-)-Anabasine

Chemical Property:

• Appearance/Colour: White fine crystalline powder
• Vapor Pressure: 0.00662mmHg at 25°C
• Melting Point: 9°C
• Refractive Index: 1.5430
• Boiling Point: 271 °C at 760 mmHg
• PKA: 8.98±0.10(Predicted)
• Flash Point: 93 ºC
• PSA: 24.92000
• Density: 1.054
• LogP: 2.22500
• Storage Temp.: Refrigerator
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.115698455
• Heavy Atom Count: 12
• Complexity: 136

Purity/Quality:

99%, ^*data from raw suppliers

(S)-Anabasine,>98%ee ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 27/28-51/53-23/24/25
• Safety Statements: 28-36/37-45-61-36/37/39-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C1CCNC(C1)C2=CN=CC=C2
• Isomeric SMILES: C1CCN[C@@H](C1)C2=CN=CC=C2
• General Description: (-)-Anabasine, also known as (S)-Anabasine, is a naturally occurring piperidine alkaloid found in tobacco, characterized by its (S)-configuration at the stereogenic center. It is synthesized enantioselectively via a vinylogous Mukaiyama–Mannich reaction, employing chiral catalysts to achieve high enantiopurity and efficiency. (-)-ANABASINE is structurally related to nicotine and exhibits biological activity, though its specific pharmacological properties depend on its stereochemistry. The efficient synthetic route highlights its significance as a target for chemical and pharmaceutical studies.

Technology Process of (-)-Anabasine

There total 44 articles about (-)-Anabasine 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: 95.0%

C10H13BrN2 (1270360-24-1) → Anabasine (494-52-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 1h; Schlenk technique;

DOI:10.1021/ja511422q

Reference yield: 95.0%

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-(S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl-tetrahydro-pyran-3-yl ester (121675-95-4) → 2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose (135865-76-8,135865-81-5,144102-44-3,148968-87-0,150737-36-3) + Anabasine (494-52-0)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1021/jo00279a001

Reference yield: 84.0%

(2S)-N-4'-nitrobenzoyl-2-(3-pyridyl)-4-piperidine (40179-50-8) → Anabasine (494-52-0)

Guidance literature:

With hydrogen bromide; acetic acid; at 80 ℃; for 45h;

DOI:10.1023/A:1010335003297

upstream raw materials:

anatabine

anabasine

(2S)-N-benzyl-2-(3-pyridyl)-piperidine

2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-2-(S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-yl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(Ξ)-1-((S)-3,4,5,6-tetrahydro-2H-[2,3']bipyridyl-1-yl)-propan-2-ol

(2S)-N-benzyl-2-(3-pyridyl)-piperidine

N-(methoxycarbonyl)anabasine

2,3'-bipyridine

Refernces

A straightforward synthesis of (S)-Anabasine via the catalytic, enantioselective vinylogous mukaiyama-Mannich reaction

10.1055/s-0029-1217026

The study presents a four-step synthesis of (S)-anabasine, a tobacco alkaloid belonging to the piperidine alkaloids group, using a catalytic, enantioselective vinylogous Mukaiyama–Mannich reaction as the key step. The synthesis involved the use of various chemicals, including 3-pyridylimine, silyl dienolates, chiral BINOL-based phosphoric acids as catalysts, and reagents such as LiBHEt3, 'hot'-Stryker reagent, DIBAL-H, and Mitsunobu reagents for reduction, cyclization, and deprotection reactions. These chemicals served to control the absolute configuration of the natural product, establish the correct absolute configuration of the stereogenic center, and convert the vinylogous Mannich product into (S)-anabasine with high enantioselectivity and efficiency. The study achieved a total yield of 55%, ranking it among the most efficient syntheses for this natural product.

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