105017-61-6

Basic information

• Product Name: (2S,6S)-2-methyl-6-undecylpiperidine
• Synonyms: Piperidine, 2-methyl-6-undecyl-, (2S,6S)-; Piperidine, 2-methyl-6-undecyl-, (2S-trans)-
• CAS NO: 105017-61-6
• Molecular Formula: C₁₇H₃₅N
• Molecular Weight: 253.4665
• Mol File: 105017-61-6.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 320.1°C at 760 mmHg
• Flash Point: 150.9°C
• Density: 0.821g/cm³
• Vapor Pressure: 0.000324mmHg at 25°C
• Refractive Index: 1.445
• CAS DataBase Reference: (2S,6S)-2-methyl-6-undecylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,6S)-2-methyl-6-undecylpiperidine(105017-61-6)
• EPA Substance Registry System: (2S,6S)-2-methyl-6-undecylpiperidine(105017-61-6)

Safety Data

• Hazardous Substances Data: 105017-61-6(Hazardous Substances Data)

Upstream product

• 693-67-4 bromoundecane 
• 1126626-80-9 (S,S)-2-methyl-6-undecyl-1-(toluene-4-sulfonyl)-piperidine 
• 75844-69-8 t-butyl piperidinecarboxylate 
• 28450-02-4 2-acetyl-6-methyl-2,3-dihydropyran 
• 99814-38-7 (Z)-Heptadec-6-en-2-one oxime 
• 132410-16-3 1-(tert-butoxycarbonyl)-6-methyl-2-n-undecyl-1,2,3,4-tetrahydropyridine 
• 1010075-98-5 N-Boc-2(S)-methyl-6(S)-undecylpiperidine 
• 88056-92-2 (-)-2-cyano-6-phenyloxazolopiperidine 
• 157766-60-4 [(S)-1-Methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid benzyl ester 
• 157766-63-7 (2S,6S)-2-Cyano-6-methyl-piperidine-1-carboxylic acid benzyl ester 
• 157766-62-6 (S)-2-Methyl-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 108818-50-4 5-lithio-2-pentanone 2',2'-dimethylpropylene ketal 
• 157766-61-5 ((S)-5-Hydroxy-1-methyl-pentyl)-carbamic acid benzyl ester 
• 104642-02-6 (2S,6S,1'R)-N-(2-hydroxy-1-phenylethyl)-2-methyl-6-undecylpiperidine 

Relevant articles and documents

Anodic cyanation of (-)-N-phenyl-2-methylpiperidine: A short synthesis of (+)-Solenopsin A and (+)-isosolenopsin A

A convenient method for the preparation of (+)-Solenopsin A 1 (5 steps, 21%) involving regiospecific anodic cyanation of (-)-N-phenyl-2-methylpiperidine 4 is described.

A versatile synthesis of (±)-solenopsin A

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Stereoselective Syntheses of cis-2-Alkyl-6-methylpiperidines

Syntheses in the pine alkaloid family, the fire ant venom series, and continued studies in the Poranthera species are presented.Reaction of 5-lithio-2-pentanone-2,2-dimethylpropylene ketal or the corresponding dialkylcuprate compound with carboxylic acid derivatives gives selectively protected 1,5-dicarbonyl compounds.After reductive amination of the newly formed ketone function, acidic hydrolysis of the cyclic ketal gives 6-alkyl-2-methyl-3,4,5,6-tetrahydropyridines.Stereoselective reduction of the imine function affords cis-2,6-disubstituted piperidines.Examplesof this approach include syntheses of dihydropinidine from Pinus sabiniana and the fire ant venoms cis-2-methyl-6-undecylpiperidine and 2-methyl-6-undecyl-3,4,5,6-tetrahydropyridine from Solenopis geminata and S. xyloni.A preliminary report on an approach to porantherilidine, from Poranthera corymbosa, is described.

Tandem overman rearrangement and intramolecular amidomercuration reactions. Stereocontrolled synthesis of cis- and frans-2,6-dialkylpiperidines

(Chemical Equation Presented) Hg(II)-mediated tandem Overman rearrangement and intramolecular amidomercuration reactions were proven to provide a convenient tool for the stereoselective synthesis of cis- and frans-2,6-disubstituted piperidines. Thus, upon treatment with Hg(OTFA) 2 in THF, the trichloroacetimidate 1 directly transformed into the 2,6-dialkyl piperidine 2 with almost exclusive trans selectivity. The amiodomercuration reaction of the carbamate 7 by Hg(OTFA)2 in nitromethane showed an excellent cis selectivity. Also reported is the stereoselective synthesis of solenopsin A and isosolenopsin A.

Hydrogenation of Pyridines Using a Nitrogen-Modified Titania-Supported Cobalt Catalyst

Novel heterogeneous catalysts were prepared by impregnation of titania with a solution of cobalt acetate/melamine and subsequent pyrolysis. The resulting materials show an unusual nitrogen-modified titanium structure through partial implementation of nitrogen into the support. The optimal catalyst displayed good activity and selectivity for challenging pyridine hydrogenation under acid free conditions in water as solvent.

Short Enantioselective Total Syntheses of the Piperidine Alkaloids (S)-Coniine and (2R,6R)-trans-Solenopsin A via Catalytic Asymmetric Imine Hydrosilylation

The enantioselective syntheses of (S)-coniine and (2R,6R)-trans-solenopsin A are reported. The key step in both syntheses is the catalytic asymmetric hydrosilylation of a cyclic imine.

SYNTHESIS OF cis AND trans-2,6-DIALKYLATED PIPERIDINES THROUGH HIGHLY REGIOSELECTIVE Α-ALKYNYLATION OF PYRIDINIUM SALTS AND ITS APPLICATION TO SYNTHESIS OF (+)-SOLENOPSINE A

Reactions of N-methoxycarbonyl-2-alkylpyridinium salts with alkynyl Grignard reagents give exclusively 2,6-disubstituted 1,2-dihydropyridines, from which cis- and trans-2,6-dialkylated piperidines can be derived selectively.Consequently, (+)-solenopsine A is efficiently synthesized by this sequence.

Stereoselective synthesis of δ-and ε-amino ketone derivatives from n-tert-butanesulfinyl aldimines and functionalized organolithium compounds?

The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a sub-sequent hydrolysis of the enol ether moiety, yielded different δ-and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the preparation of 2-substituted 6-methylpiperidines in a stereoselective manner, among them natural alkaloids (+)-and (?)-isosolenopsin A.

SOLENOPSIN AND DERIVATIVES, THERAPEUTIC COMPOSITIONS, AND METHODS RELATED THERETO

This disclosure relates to solenopsin derivatives, pharmaceutical compositions, and therapeutic uses related thereto. In certain embodiments, the disclosure relates to compounds of the following formula: or salts, esters or prodrugs thereof as described herein.