54985-88-5

Usage

Properties and Specific Content of 1-Ethyl-3-(2-methylbutyl)piperidine

A compound consisting of 13 carbon atoms, 25 hydrogen atoms, and 1 nitrogen atom.

Chemical Classification

Piperidine Derivative
A compound derived from the six-membered heterocyclic aromatic piperidine ring structure.

Usage

Synthesis of Other Organic Compounds
Acts as a precursor or intermediate in chemical reactions to produce various other organic molecules.
4. Potential Central Nervous System Depressant
May have an effect on the nervous system, reducing its activity and causing sedation or reduced alertness.
5. Possible Sedative Effects
Can induce a calming or soothing effect, potentially leading to drowsiness or relaxation.
6. Possible Analgesic Effects
May help alleviate pain by interacting with the body's pain receptors or pathways.
7. Hazardous if Mishandled
Requires careful handling and storage to avoid potential health or environmental risks.
8. Potential Applications in Research and Pharmaceutical Development
The unique chemical structure and properties make it a valuable compound for studying and developing new medications or therapies.

InChI:InChI=1/C12H25N/c1-4-11(3)9-12-7-6-8-13(5-2)10-12/h11-12H,4-10H2,1-3H3

Upstream product

• 108-99-6 3-Methylpyridine 
• 152615-80-0 (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine 
• 850442-83-0 (R)-3-((S)-2-Methyl-butyl)-piperidine 
• 1352632-75-7 (S)-4-isopropyl-3-{5-[(S)-2-methylbutyl]pyridin-2-yl}-oxazolidin-2-one 
• 75-07-0 acetaldehyde 
• 1352632-76-8 (S)-2-chloro-5-(2-methylbutyl)pyridine 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 1352632-83-7 (R)-4-isopropyl-3-{5-[(S)-2-methylbutyl]pyridin-2-yl}oxazolidin-2-one 
• 500-22-1 3-pyridinecarboxaldehyde 
• 1352632-87-1 (S)-4-isopropyl-3-{5-[(R)-2-methylbutyl]pyridin-2-yl}oxazolidin-2-one 
• 1352632-79-1 (S)-3-methyl-4-(pyridin-3-yl)butan-2-ol 
• 1352632-80-4 O-[(S)-1,2-dimethyl-3-(pyridin-3-yl)propyl] imidazole-1-carbothioate 
• 1352632-84-8 (S)-2-chloro-5-(2-methylbutyl)pyridine 
• 421582-72-1 (S)-3-methyl-4-(pyridin-3-yl)butan-2-one 

Relevant academic research and scientific papers

Enantioselective Synthesis and Determination of the Configuration of Stenusine, the Spreading Agent of the Beetle Stenus comma

The enantioselective total synthesis of two of the four possible stereoisomers of stenusine (1), the spreading agent of the beetle Stenus comma, is described.The silyl ether-substituted aldehyde SAMP hydrazone 2 was alkylated with (S)-1-bromo-2-methylbutane (3) yielding the hydrazone 4 in high diastereomeric purity (de>95percent).By several steps including the reduction of the hydrazone functionality and the cleavage of the N-N bond of the intermediates, 4 was converted into the BOC-protected amino alcohol 6.Subsequent cyclization of 6 afforded the (S,S) diastereomer of stenusine with 96.6percent de, >99.9percent ee, and in 11.3percent overall yield.Repetition of this synthesis using the aldehyde RAMP hydrazone (R)-2 as the starting material produced (S,R)-1 with 95.0percent de, >99percent ee, and in 8.2percent overall yield.The synthetic samples of 1 were employed to investigate the stereochemistry of natural stenusine by means of GC analysis on both a chiral and an achiral, stationary phase.As a result of these studies natural stenusine was found to be a mixture of all four stereoisomers in a ratio of (S,S)/(S,R)/(R,R)(R,S)=43:40:13:4.

Straightforward synthesis of all stenusine and norstenusine stereoisomers

All the stereoisomers of stenusine (1) and norstenusine (21) have been efficiently synthesized by the asymmetric hydrogenation of pyridines. The (2R,3S)- and (2R,3R)-isomers of 1, that are difficult to prepare, have been synthesized for the first time using a chemoenzymatic approach in eight steps with an 8 % total yield. All the target compounds were obtained in good stereochemical purity by using very simple and inexpensive reagents and auxiliaries. All the stereoisomers of the defensive alkaloids stenusine and norstenusine produced by Stenus beetles have been synthesized in a straightforward manner. The chiral (S) side chain is derived from (S)-2-methyl-1-butanol. For the difficult preparation of (R)-3-(2-methylbutyl) pyridine, a highly efficient chemoenzymatic approach was developed.

Short synthesis of stenusine and norstenusine, two spreading alkaloids from Stenus beetles (Coleoptera: Staphylinidae)

Each of the both spreading alkaloids stenusine and norstenusine could be synthesized starting from commercially available 3-picoline in a two-step synthesis in yields of 74% and 67% in gram scale. The stereoisomeric ratio of the synthesized (+)-stenusine is similar to that of stenusine from Stenus comma.

Efficient preparation of (1′R)-(-)-1-(2′-hydroxy-1′- phenylethyl)piperidin-2-one: Synthesis of (2′S,3R)-(+)-stenusine

An efficient oxidation of (2′R)-(-)-2′-phenyl-2′- (piperidin-1-yl)ethanol 2 with bromine to generate the corresponding piperidin-2-one 3 in 96% is described. In addition, starting from 3, (2′S,3R)-(+)-stenusine 8 was synthesized in 70% overall yield. The

An expeditious total synthesis of the natural stereomeric mixture of stenusine following a possible biogenetic pathway

New insight into the biogenetic origin of stenusine 1, the spreading agent of the beetle Stenus comma, is gained from the results of a one-pot synthesis of the natural and the racemic compound. On the basis of these results a plausible biogenetic pathway

Asymmetric synthesis. XXX. Synthesis of 3-substituted piperidines from chiral non-racemic lactams

A series of 3-substituted piperidines in enantiomerically pure form has been synthesized from lactam 3 by a stereospecific route involving a postulated rigid amide enolate. This strategy has been applied to the synthesis of (+)-stenusine 10.

Synthesis of Stenusine, the Spreading Agent of the Beetle Stenus comma

Stenusine, , the spreading agent of Stenus comma, was synthesized by a six-step sequence in 21 percent overall yield from acetaldehyde.Acetaldehyde was converted into the corresponding N-tert-butyl aldimine, which was sequentially alkylated via its 1-azaallylic anion with 1-bromo-2-methylbutane and 1-bromo-3-chloropropane.The resulting δ-chloro-aldimine was hydrolyzed into the δ-chloro aldehyde, which was converted into the corresponding N-ethyl-aldimine.The latter labile δ-chloro aldimine was cyclized with lithium aluminum hydride to afford stenusine.The 1-tert-butyl analogue of stenusine was synthesized using an analogous route.