(-)-Coniine

Base Information

• Chemical Name: (-)-Coniine
• CAS No.: 5985-99-9
• Molecular Formula: C8H17N
• Molecular Weight: 127.23
• European Community (EC) Number: 207-282-6
• UNII: QKK1SI92BR
• DSSTox Substance ID: DTXSID301019378
• Nikkaji Number: J259.953H
• Wikipedia: Coniine
• Wikidata: Q27287308
• NCI Thesaurus Code: C87476
• Mol file: 5985-99-9.mol

Synonyms:cicutine;conicine;coniine;coniine hydrobromide, (S)-isomer;coniine hydrochloride, (+-)-isomer;coniine hydrochloride, (S)-isomer;coniine, (+-)-isomer;coniine, (S)-isomer;koniin

Chemical Property of (-)-Coniine

Chemical Property:

• PSA: 12.03000
• LogP: 2.25740
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 127.136099547
• Heavy Atom Count: 9
• Complexity: 71

Purity/Quality:

98%min ^*data from raw suppliers

(R)-2-PROPYLPIPERIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CCCC1CCCCN1
• Isomeric SMILES: CCC[C@@H]1CCCCN1

Technology Process of (-)-Coniine

There total 17 articles about (-)-Coniine 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: 39.0%

C15H20O2 + rac-coniine (3238-60-6) → (R)-1-(3-mesitylpropanoyl)-2-propylpiperidine + (S)-1-(3-mesitylpropanoyl)-2-propylpiperidine (1346681-80-8) + R(-)-coniine (5985-99-9)

Guidance literature:

With 2-(2,4,6-trimethyl-phenyl)-2,5,6,7-tetrahydro-pyrrolo[2,1-c] [1,2,4]triazol-4-ylium perchlorate; (4aR,9aS)-6-bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one; potassium carbonate; In Isopropyl acetate; at 23 ℃; for 24h; Resolution of racemate;

DOI:10.1039/c2cc34907h

Reference yield:

(E)-octa-5,7-dien-1-amine (121044-85-7) → R(-)-coniine (5985-99-9) + coniine (458-88-8)

Guidance literature:

(E)-octa-5,7-dien-1-amine; With (S)-Me2Si(η⁵-OHF)(η⁵-C5H3(-)-menthyl)Smn(TMS)2; In benzene-d6; at 25 ℃; for 168h;

With sodium hydroxide; benzyl chloroformate; In diethyl ether; benzene-d6;

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/ja036266y

Reference yield:

4-tert-butyl-3-(6-isopropyl-pyridin-2-yl)-oxazolidin-2-one → R(-)-coniine (5985-99-9) + coniine (458-88-8)

Guidance literature:

With hydrogen; acetic acid; palladium dihydroxide; at 40 ℃; for 22h; under 75006 Torr; Title compound not separated from byproducts;

DOI:10.1002/anie.200453942

upstream raw materials:

(1S,2R)-1-Phenyl-2-((S)-2-propyl-piperidin-1-yl)-propan-1-ol

(S)-1-Benzyl-2-((E)-propenyl)-piperidine

rac-coniine

3-{bis[(S)-2-acetoxypropanoyl]amino}-2-diphenylmethylquinazolin-4(3H)-one

Refernces

Versatile one-pot reductive alkylation of lactams/amides via amide activation: Application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine

10.1002/chem.201002054

The research focuses on the development of a versatile one-pot reductive alkylation method for the transformation of lactams and amides into α-substituted amines, which are key structural features in many bioactive alkaloids and pharmaceutically relevant molecules. The study aimed to improve the efficiency of organic synthesis by utilizing a triflic anhydride (Tf2O)/2,6-di-tert-butyl-4-methylpyridine (DTBMP) combination as the amide activating system, Grignard reagents as alkylating agents, and lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) as reducing agents. The methodology was demonstrated through the concise syntheses of bioactive alkaloids (-)-bgugaine, (-)-coniine, (+)-preussin, and (-)-cassine, showcasing the method's diastereoselectivity and versatility. The successful syntheses of these alkaloids not only highlight the efficiency of the developed method but also its potential for further application in the total synthesis of other alkaloids.