139894-04-5

Basic information

• Product Name: 3(2H)-Indolizinone, hexahydro-, (S)-
• CAS NO: 139894-04-5
• Molecular Formula: C8H13NO
• Mol File: 139894-04-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3(2H)-Indolizinone, hexahydro-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Indolizinone, hexahydro-, (S)-(139894-04-5)
• EPA Substance Registry System: 3(2H)-Indolizinone, hexahydro-, (S)-(139894-04-5)

Safety Data

• Hazardous Substances Data: 139894-04-5(Hazardous Substances Data)

Upstream product

• 139894-03-4 S-(+)-methyl O-(7R,8aR)-3-oxoindolizidin-7-yl dithiocarbonate 
• 139750-90-6 (1R,2S,5R/S,6R,7S)-(+)-4-(but-3'-ynyl)-5-hydroxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 139894-01-2 (1S,2R,3S,5R,10S,11R)-(+)-9-oxo-8-azatetracyclo<9.2.1.0^2,10.0^3,8>tetradec-12-en-5-yl formate 
• 82478-74-8 (1R,2S,5R/S,6R,7S)-(+)-4-(buten-3-yl)-5-hydroxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 139750-97-3 (1S,2R,3S,5R,10S,11R)-(+)-5-hydroxy-8-azatetracyclo<9.2.1.0^2,10.0^3,8>tetradec-12-en-9-one 
• 139894-02-3 (7R,8aR)-(+)-7-hydroxyindolizidin-3-one 
• 139750-98-4 (7R,8aS)-(+)-6,7,8,8a-tetrahydro-7-hydroxyindolizin-3(5H)-one 
• 393827-08-2 1-(2-vinylpiperidin-1-yl)propenoate 
• 359866-35-6 6,7,8,8a-tetrahydro-5H-indolizin-3-one 
• 212556-97-3 (S)-2-((E)-2-Methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid benzyl ester 
• 212556-98-4 (S)-2-((E)-2-Methoxycarbonyl-vinyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 3433-37-2 piperidin-2-ylmethanol 
• 157634-00-9 tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate 
• 212556-95-1 (S)-N-(benzyloxycarbonyl)-2-formylpiperidine 

Downstream Products

• 18881-13-5 (+)-coniceine 

Relevant articles and documents

A Novel Approach to Bicyclic Alkaloids Using a Tandem Diastereoselective Acyliminocyclization and Retro Diels-Alder Reaction Sequence. Synthesis of (+)-Indolizidine and (+)-Laburnine

A new aproach to diastereoselective cationic cyclization by stereocontrol due to the bicycloheptene moiety in a chiral γ-hydroxy lactam is described.The diastereoselective reaction followed by Diels-Alder cycloreversion has ben succesfully applied to a chiral synthesis of (+)-indolizidine and (+)-laburnine (=trachelanthamidine).

Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

The kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2- (hydroxymethyl)piperidine [(±)-5] and (±)-N(tert-butoxycarbonyl)-2- (hydroxymethyl)piperidine [(±)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)- 6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2- 4 steps) and proceeded with satisfactory overall yield.