(2S,6S)-2-methyl-6-undecylpiperidine

Base Information

• Chemical Name: (2S,6S)-2-methyl-6-undecylpiperidine
• CAS No.: 35285-25-7
• Molecular Formula: C17H35 N
• Molecular Weight: 253.472
• Hs Code.: 2933399090
• UNII: WSD24XFN6C
• DSSTox Substance ID: DTXSID30913351
• Nikkaji Number: J341.242C
• Mol file: 35285-25-7.mol

Synonyms:cis-2-methyl-6-n-undecylpiperidine;isosolenopsin A;Solenopsin A;trans-2-methyl-6-n-undecylpiperidine

Chemical Property of (2S,6S)-2-methyl-6-undecylpiperidine

Chemical Property:

• Vapor Pressure: 0.000324mmHg at 25°C
• Boiling Point: 320.1°Cat760mmHg
• PKA: 10.78±0.10(Predicted)
• Flash Point: 150.9°C
• PSA: 196.04000
• Density: 0.821g/cm³
• LogP: 0.87600
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 253.276950121
• Heavy Atom Count: 18
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC1CCCC(N1)C
• Isomeric SMILES: CCCCCCCCCCC[C@H]1CCC[C@@H](N1)C

Technology Process of (2S,6S)-2-methyl-6-undecylpiperidine

There total 164 articles about (2S,6S)-2-methyl-6-undecylpiperidine 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: 96.0%

tert-butyl (2R,6R)-(-)-2-methyl-6-undecyl-piperidine-1-carboxylate (160549-82-6) → (2R,6R)-(-)-2-methyl-6-undecylpiperidine (28720-60-7,35285-24-6,35285-25-7,63950-16-3,76094-26-3,83709-88-0,92619-72-2,137038-57-4,137038-58-5,105017-61-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1002/jhet.5570450112

Reference yield: 82.0%

(2R,6R)-trans-N-Benzyl-2-undecyl-6-methylpiperidine → (2R,6R)-(-)-2-methyl-6-undecylpiperidine (28720-60-7,35285-24-6,35285-25-7,63950-16-3,76094-26-3,83709-88-0,92619-72-2,137038-57-4,137038-58-5,105017-61-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; under 3800 Torr; Ambient temperature;

DOI:10.1002/recl.19951140405

Reference yield: 77.0%

(8R,10R)-8-methyl-10-undecyl-1,5-dithia-9-azaspiro[5.5]undecane → (2R,6R)-(-)-2-methyl-6-undecylpiperidine (28720-60-7,35285-24-6,35285-25-7,63950-16-3,76094-26-3,83709-88-0,92619-72-2,137038-57-4,137038-58-5,105017-61-6)

Guidance literature:

With hydrogen; In ethanol; for 3.5h; Reflux;

DOI:10.1039/c8ob01363b

upstream raw materials:

tert-butyl (2R,6R)-(-)-2-methyl-6-undecyl-piperidine-1-carboxylate

methyllithium

(2R,6R)-[(1R)-2-hydroxy-1-phenylethyl]-2-methyl-6-undecylpiperidine

4,8-dihydroxy-1,10-undecanediene

Refernces

An enantioselective route to trans-2,6-disubstituted piperidines

10.1016/S0040-4020(97)00377-3

The study presents an enantioselective synthetic route to trans-2,6-disubstituted piperidines, focusing on the synthesis of (S)-2-methyl tetrahydropyridine-N-oxide, a key intermediate. This compound is crucial for constructing trans-2,6-disubstituted piperidines via a [3+2] nitrone cycloaddition reaction. The research demonstrates the utility of this method by synthesizing the fire ant venom alkaloid, (+)-solenopsin-A, through a series of steps including nitrone formation, cycloaddition, and reductive cleavage. The methodology is highlighted for its potential application in synthesizing similar piperidine-based alkaloids, with implications for pharmaceuticals, such as treatments for Alzheimer's disease.

Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin a: Application of a gold-catalyzed cyclization

10.1039/c2ob25685a

The research focuses on the total synthesis of piperidine alkaloids, specifically (+)-241D, isosolenopsin, and isosolenopsin A, which are derived from D-alanine. The study employs a gold-catalyzed cyclization as the key step to access the chiral pyridinone intermediates, which are crucial for the synthesis of these alkaloids. The synthesis involves multiple steps, including the preparation of chiral synthons, gold-catalyzed intramolecular cyclization, and stereoselective reductions. The experiments utilized various reactants such as N-Boc-D-alanine, undecyne, BuLi, PPh3AuCl, and AgSbF6, among others, and employed techniques like Arndt–Eistert homologation and catalytic hydrogenation. The synthesized compounds were analyzed using spectroscopic methods (1H and 13C NMR, IR, and HRMS) and optical rotation measurements to confirm their structures and enantiomeric purity.

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