35285-24-6

Basic information

• Product Name: (2R,6S)-Isosolenopsine A
• Synonyms: (+)-Isosolenopsin A;(2R)-2α-Methyl-6α-undecylpiperidine;(2R,6S)-2-Methyl-6-undecylpiperidine;(2R,6S)-Isosolenopsine A;2β-Undecyl-6β-methylpiperidine;(2S,6R)-2-Methyl-6-undecylpiperidine;(2S,6R)-Isosolenopsine A
• CAS NO: 35285-24-6
• Molecular Formula: C₁₇H₃₅N
• Molecular Weight: 253.47
• Mol File: 35285-24-6.mol
• Article Data: 37

Chemical Properties

• Boiling Point: 320.1±10.0 °C(Predicted)
• Appearance: /
• Density: 0.821±0.06 g/cm3(Predicted)
• PKA: 10.78±0.10(Predicted)
• CAS DataBase Reference: (2R,6S)-Isosolenopsine A(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,6S)-Isosolenopsine A(35285-24-6)
• EPA Substance Registry System: (2R,6S)-Isosolenopsine A(35285-24-6)

Safety Data

• Hazardous Substances Data: 35285-24-6(Hazardous Substances Data)

Upstream product

• 160549-82-6 tert-butyl (2R,6R)-(-)-2-methyl-6-undecyl-piperidine-1-carboxylate 
• 917-54-4 methyllithium 
• 503843-27-4 (2R,6R)-[(1R)-2-hydroxy-1-phenylethyl]-2-methyl-6-undecylpiperidine 
• 111512-38-0 4,8-dihydroxy-1,10-undecanediene 
• 184535-10-2 (2S,6R)-2-allyl-6-methylpiperidine-1-carboxylic acid tert-butyl ester 
• 473893-70-8 (4RS,6S,10S)-1-aza-4-(iodomethyl)-3-oxa-10-methyl-2-enylbicyclo-[4.4.0]decan-2-one 
• 473893-68-4 methyl (2S,6S)-2,6-bis(2-propenyl)piperidinecarboxylate 
• 473893-69-5 (4RS,6S,10S)-1-aza-4-(iodomethyl)-3-oxa-10-prop-2-enylbicyclo[4.4.0]-decan-2-one 
• 473893-67-3 (2S,6S)-1-benzyl-2,6-bis(2-propenyl)piperidine 
• 473893-71-9 (2R,6S)-2-Methyl-6-((E)-undec-2-enyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 888745-46-8 (R)-Undeca-1,10-diene-4,8-diol 
• 958003-20-8 C₂₅H₃₂O₆S₂ 
• 693-67-4 bromoundecane 
• 6280-87-1 δ-chlorovaleronitrile 

Relevant articles and documents

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.

Stereoselective synthesis of 2,6-: Trans -4-oxopiperidines using an acid-mediated 6- endo-trig cyclisation

An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (-)-solenopsin A.

Metal-free borane-catalyzed highly stereoselective hydrogenation of pyridines

A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C 6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.