92721-60-3

Basic information

• Product Name: 1,2,5,7a-tetrahydro-7-(hydroxyMethyl)-3H-Pyrrolizin-3-one
• Synonyms: 1,2,5,7a-tetrahydro-7-(hydroxyMethyl)-3H-Pyrrolizin-3-one
• CAS NO: 92721-60-3
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.17844
• Mol File: 92721-60-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2,5,7a-tetrahydro-7-(hydroxyMethyl)-3H-Pyrrolizin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,5,7a-tetrahydro-7-(hydroxyMethyl)-3H-Pyrrolizin-3-one(92721-60-3)
• EPA Substance Registry System: 1,2,5,7a-tetrahydro-7-(hydroxyMethyl)-3H-Pyrrolizin-3-one(92721-60-3)

Safety Data

• Hazardous Substances Data: 92721-60-3(Hazardous Substances Data)

Upstream product

• 116071-96-6 6-hydroxymethyl-6-phenylsulphinyl-1-azabicyclo<3.3.0>octan-2-one 
• 103979-77-7 1-(3-ethoxycarbonylpropyl)pyrrolidine-2,5-dione 
• 122695-52-7 6-hydroxymethyl-6-phenylthio-1-azabicyclo<3.3.0>octan-2-one 
• 86436-55-7 5-ethoxy-1-<2-(phenylthio)ethyl>pyrrolidin-2-one 
• 146336-56-3 7-(Tributylstannanyl-trimethylsilanyl-methyl)-1,2,5,7a-tetrahydro-pyrrolizin-3-one 
• 116071-86-4 5-ethoxy-1-(3-ethoxycarbonylpropyl)pyrrolidin-2-one 
• 146336-67-6 6-Bromo-7-[1-trimethylsilanyl-meth-(Z)-ylidene]-hexahydro-pyrrolizin-3-one 
• 146336-70-1 7-(Bromo-trimethylsilanyl-methyl)-1,2,5,7a-tetrahydro-pyrrolizin-3-one 
• 85540-31-4 7-methylenetetrahydro-1H-pyrrolizin-3(2H)-one 
• 83177-79-1 (+/-)-1-Aza-4-formylbicyclo<3.3.0>oct-3-en-8-one 
• 87449-77-2 5-ethoxy-1-(2'-propen-1'-yl)-2-pyrrolidinone 
• 103979-79-9 1-(3-ethoxycarbonyl-3-hydroxymethylenepropyl)-5-phenyl-thiopyrrolidin-2-one 
• 146336-62-1 1-(2,2-Bis-phenylsulfanyl-ethyl)-5-trimethylsilanylethynyl-pyrrolidin-2-one 
• 146336-63-2 1-(2-Benzenesulfonyl-2-chloro-ethyl)-5-trimethylsilanylethynyl-pyrrolidin-2-one 

Downstream Products

• 23185-51-5 (+/-)-supinidine 

Relevant articles and documents

Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates

We have developed a phosphine-catalyzed (4+1) annulative rearrangement for the preparation of 3-pyrrolines from allenylic carbamates via phosphonium diene intermediates. We employed this methodology to synthesize an array of 1,3-disubstituted- and 1,2,3-t

Transalpinecine and Analogues: First Total Synthesis, Stereochemical Revision and Biological Evaluation

The first total synthesis of transalpinecine, a pyrrolizidine alkaloid extracted from Heliotropium transalpinum is reported. The concise synthetic route developed towards these unusual iminosugar-like natural compounds relies on an intramolecular Morita–Baylis–Hillman reaction. The four diastereoisomers of transalpinecine, as well as the two diastereoisomers of the parent epoxide subulacine, were prepared. 1H NMR-based stereochemical assignment of these different diastereoisomers was substantiated by quantum calculations of NMR shifts and coupling constants, allowing revision of the initially reported transalpinecine structure. One of these synthetic compounds significantly potentiates the activity of the F508del-CFTR corrector VX-809.

A radical approach to the synthesis of (±)-supinidine

Intramolecular addition of α-sulfonyl radicals to triple bonds followed by addition of tin radicals to the resulting allylsulfones gave pyrrolizidine skeletons. Subsequent manipulations led to a formal synthesis of (±)-supinidine.

A Novel Synthesis of Pyrrolizidine Alkaloids by Means of an Intramolecular Carbenoid Displacement (ICD) Reaction

The pyrrolizidine alkaloids, (+/-)-trachelanthamidine, (+/-)-isoretronecanol, and (+/-)-supinidine were synthesized by using an intramolecular carbenoid displacement (ICD) reaction of the diazo-sulphide or the diazo-selenide derivatives as a key step.

Pyrrolizidinone and Indolizidinone Synthesis: Generation and Intramolecular Addition of α-Acylamino Radicals to Olefins and Allenes

α-Acylamino radicals can be generated by treatment of phenylthio, methylthio, or phenylselenyl lactams of type 7, 8, and 17 with tri-n-butyltin hydride in the presence of AIBN.The radicals add intramolecularly to olefins and allenes to give indolizidinones and pyrrolizidinones.The product distribution depends on the substitution patterns of the unsaturated moiety and the legnth of the chain connecting the radical and olefinic centers.Product ratios appear to reflect the kinetic partitioning of the radical between cyclization pathways.These reactions are potentially useful in the area of pyrrolizidine alkaloid synthesis.The conversion of cyclization produts 50 and 51 to (+/-)-supinidine (1) serves as an example.