184535-05-5

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 2-(2-propenyl)-, phenylmethyl ester, (2R)-
• CAS NO: 184535-05-5
• Molecular Formula: C16H21NO2
• Molecular Weight: 259.348
• Mol File: 184535-05-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 2-(2-propenyl)-, phenylmethyl ester, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 2-(2-propenyl)-, phenylmethyl ester, (2R)-(184535-05-5)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 2-(2-propenyl)-, phenylmethyl ester, (2R)-(184535-05-5)

Safety Data

• Hazardous Substances Data: 184535-05-5(Hazardous Substances Data)

Upstream product

• 1191-30-6 5-bromopentanal 
• 1351810-75-7 (2R,RS)-2-allyl-(N-tert-butylsulfinyl)piperidine 
• 501-53-1 benzyl chloroformate 
• 1000806-52-9 (E)-(7-benzyloxycarbonylamino)-2-heptenal 
• 139163-21-6 (R)-2-allylpiperidine hydrochloride 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 143264-57-7 (R)-1-(benzyloxycarbonyl)-2-(2-oxoethyl)piperidine 

Downstream Products

• 143264-57-7 (R)-1-(benzyloxycarbonyl)-2-(2-oxoethyl)piperidine 
• 1407484-41-6 (2R,2′R,S_S)-1-(benzyloxycarbonyl)-2-[2′-tert-(butylsulfinamide)-4′-pentenyl]piperidine 
• 1407484-43-8 (2R,2′S,R_S)-1-(benzyloxycarbonyl)-2-[2′-tert-(butylsulfinamide)-4′-pentenyl]piperidine 
• 2858-66-4 (-)-pelletierine 
• 41447-16-9 (+)-N-methylallosedridine 
• 26171-47-1 1-piperidin-2-yl-propan-2-ol 
• 190383-57-4 [2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-epoxypropyl)piperidine 
• 190383-58-5 [2R-(2R)]-1-benzyloxycarbonyl-2-(2,3-epoxypropyl)piperidine 
• 190383-62-1 [2R-(2R)]-1-benzyloxycarbonyl-2-(2-hydroxy-4-pentenyl)piperidine 
• 26648-71-5 (-)-halosaline 
• 190383-53-0 [2R-(2S)]-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)piperidine 
• 190383-54-1 [2R-(2R)]-1-benzyloxycarbonyl-2-(2,3-dihydroxypropyl)piperidine 
• 458-88-8 coniine 

Relevant articles and documents

Concise total synthesis and stereochemical analysis of tetraponerines T3 and T4

An efficient stereocontrolled preparation of tetraponerines T3 and T4 is detailed. The sequence takes advantage of two consecutive stereoselective aminoallylations of appropriate aldehydes with chiral tert-butanesulfinamide and in situ generated allyl indium species. The absolute configuration of the carbon stereogenic center at the aminal moiety is thermodynamically controlled. This was ascertained on the basis of an exhaustive DFT configurational study of tetraponerines, which fulfils the lack of detailed structural information for these systems. It was found that the trans-transoid-configuration of the AB rings is the most stable geometry for T3 and T4. However, the C ring prefers a cis-configuration in T3 (ttc-T3) and a trans-fusion in T4 (ttt-T4). Regarding their dynamic behavior, low activation barriers were found by DFT calculations for the inversion of the nitrogen at the indolizidine framework, allowing rapid equilibration between the major configurations (ttc and ttt) in T3 and T4.

A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine, (-)-pelletierine, (+)-δ-coniceine, and (+)-epidihydropinidine

A new asymmetric route to 2-substituted piperidines involving the Sharpless asymmetric dihydroxylation (AD) of 5-hexenylazide 1 and an intramolecular aminocyclization as crucial steps and its application to the asymmetric synthesis of four piperidine alkaloids, (+)-coniine 2, (-)-pelletierine 3, (+)-δ-coniceine 4, aND (+)-epidihydropinidine 5 is presented.