5096-50-4

Basic information

• Product Name: CROTANECINE
• Synonyms: CROTANECINE
• CAS NO: 5096-50-4
• Molecular Formula: C8H13NO3
• Molecular Weight: 171.19372
• Mol File: 5096-50-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 369.6°Cat760mmHg
• Flash Point: 227.9°C
• Appearance: /
• Density: 1.45g/cm³
• Vapor Pressure: 5.73E-07mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: CROTANECINE(CAS DataBase Reference)
• NIST Chemistry Reference: CROTANECINE(5096-50-4)
• EPA Substance Registry System: CROTANECINE(5096-50-4)

Safety Data

• Hazardous Substances Data: 5096-50-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H13NO3/c10-4-5-1-2-9-3-6(11)8(12)7(5)9/h1,6-8,10-12H,2-4H2/t6-,7-,8-/m1/s1

Upstream product

• 132216-44-5 (3aR,8aR,8bS)-2,2-Dimethyl-3a,6,8a,8b-tetrahydro-4H-[1,3]dioxolo[4,5-a]pyrrolizine-8-carboxylic acid methyl ester 
• 132216-39-8 Toluene-4-sulfonic acid (4R,5S)-2,2-dimethyl-5-[(Z)-4-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-[1,3]dioxolan-4-ylmethyl ester 
• 132216-40-1 (3aR,6aS)-2,2-Dimethyl-6-[3-(tetrahydro-pyran-2-yloxy)-propyl]-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 132216-38-7 1-((3aS,6aR)-2,2-Dimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-cyclopropanecarboxylic acid methyl ester 
• 132216-02-5 (3aR,8aR,8bS)-2,2-Dimethyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizine-8-carboxylic acid methyl ester 
• 95687-38-0 (2R,6R,7S,7aR)-2,7-Diacetoxy-6-(tert-butyl-dimethyl-silanyloxy)-hexahydro-pyrrolizine-1-carboxylic acid ethyl ester 
• 95687-39-1 (6R,7S,7aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,7-dihydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid ethyl ester 
• 95687-37-9 (2R,6R,7S,7aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,7-dihydroxy-hexahydro-pyrrolizine-1-carboxylic acid ethyl ester 
• 95726-76-4 (1S,5R,8R)-ethyl 8-(dimethyl-t-butylsiloxy)-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate 
• 95687-56-2 (1S,5R,8R)-ethyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate 
• 95687-36-8 (6R,7S,7aR)-6,7-Diacetoxy-5,6,7,7a-tetrahydro-3H-pyrrolizine-1-carboxylic acid ethyl ester 
• 132216-43-4 (3aR,8R,8aS,8bS)-2,2-Dimethyl-8-phenylselanyl-hexahydro-[1,3]dioxolo[4,5-a]pyrrolizine-8-carboxylic acid methyl ester 
• 132216-03-6 4-Chloro-2-[(3aS,6aR)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-(4Z)-ylidene]-butyric acid methyl ester 
• 132216-41-2 2-[(3aS,6aR)-2,2-Dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-(4Z)-ylidene]-4-hydroxy-butyric acid methyl ester 

Relevant articles and documents

Tandem [4 + 2]/[3 + 2] cycloadditions of nitroalkenes. 11. The synthesis of (+)-crotanecine

(+)-Crotanecine (1) is the necine base component of a number of pyrrolizidine alkaloids. This necine subunit is an amino triol bearing a primary allylic alcohol characterized by an all-cis relationship of its stereocenters. The synthesis of (+)-crotanecine has been accomplished in 10 steps and 10.2% overall yield. The key step in the asymmetric synthesis is a Lewis acid-promoted, tandem inter[4 + 2]/intra[3 + 2] cycloaddition between a (fumaroyloxy)nitroalkene 14 and chiral β-silylvinyl ether (-)-26. This synthesis serves to illustrate the synthetic versatility of the tandem cycloaddition to incorporate additional functionality.

AN ENANTIOSELECTIVE SYNTHESIS OF (+)-CROTANECINE

(2S,4R)-4-Hydroxyproline was elaborated into (+)-crotanecine via (1S,5R,8R)-8-hydroxy-2-oxa-6-azabicyclooctan-3-one