517-81-7

Basic information

• Product Name: uleine
• Synonyms: uleine;(12S)-2-Methyl-6-methylene-12-ethyl-1β,5β-methano-2,3,4,5,6,7-hexahydro-1H-azocino[4,3-b]indole;[12S,(+)]-12-Ethyl-2,3,4,5,6,7-hexahydro-2-methyl-6-methylene-1β,5β-methano-1H-azocino[4,3-b]indole
• CAS NO: 517-81-7
• Molecular Formula: C18H22N2
• Molecular Weight: 266.3807
• Mol File: 517-81-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 437.6°Cat760mmHg
• Flash Point: 218.5°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: uleine(CAS DataBase Reference)
• NIST Chemistry Reference: uleine(517-81-7)
• EPA Substance Registry System: uleine(517-81-7)

Safety Data

• Hazardous Substances Data: 517-81-7(Hazardous Substances Data)

Usage

Description

Uleine is an Aspidosperma alkaloid found in several members of the Aspidosperma species, particularly in A. ulei. It forms colorless crystals with a specific double melting point and exhibits slight dextrorotatory optical activity. Uleine has a characteristic ultraviolet spectrum with two absorption maxima, and its hydrochloride and methiodide derivatives have distinct melting points. Oxidation with KMnO4 results in the formation of formaldehyde, indicating the presence of an exocyclic methylene group.

Uses

1. Used in Pharmaceutical Industry:
Uleine is used as a pharmaceutical compound for its alkaloid properties, which can be further explored for potential therapeutic applications.
2. Used in Chemical Research:
Uleine is used as a research compound in the study of Aspidosperma alkaloids, their properties, and their potential applications in various fields.
3. Used in Organic Chemistry:
Uleine is used as a starting material or intermediate in the synthesis of other complex organic compounds, taking advantage of its unique structural features and reactivity.
4. Used in Analytical Chemistry:
Uleine is used as a reference compound for the development and validation of analytical methods, such as spectroscopic techniques, due to its characteristic spectral properties.
5. Used in Toxicology Studies:
Uleine can be used in toxicological research to understand the effects of alkaloids on biological systems and to develop potential detoxification strategies.
6. Used in Drug Delivery Systems:
Similar to gallotannin, uleine could potentially be incorporated into drug delivery systems to improve its bioavailability and therapeutic outcomes, although further research would be required to explore this application.

References

Schmutz, Hunziker, Hirt., Helv. Chim. Acta, 40, 1189 (1957) Schmutz, Hunziker, Hirt., ibid, 41, 288 (1958) Buchi, Warnhoff.,J. Amer. Chem. Soc., 81,4433 (1959) Ondetti, Deulofeu., Tetrahedron Lett., No.7, 1 (1959) Synthesis: Wilson et ai., Chem. Commun., 584 (1968)

InChI:InChI=1/C18H22N2/c1-4-12-13-9-10-20(3)18(12)16-14-7-5-6-8-15(14)19-17(16)11(13)2/h5-8,12-13,18-19H,2,4,9-10H2,1,3H3/t12-,13-,18+/m0/s1

Upstream product

• 60553-32-4 1-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,6-tetrahydropyridine 
• 189952-78-1 (2-{(S)-4-[2-(Benzyl-tert-butoxycarbonyl-amino)-ethyl]-5-[1,3]dioxan-2-yl-hept-1-ynyl}-phenyl)-carbamic acid ethyl ester 
• 189952-80-5 Benzyl-[(R)-4-[1,3]dioxan-2-yl-3-(1H-indol-2-ylmethyl)-hexyl]-carbamic acid tert-butyl ester 
• 189952-77-0 Benzyl-[(S)-3-(1-[1,3]dioxan-2-yl-propyl)-hex-5-ynyl]-carbamic acid tert-butyl ester 
• 189952-75-8 (S)-3-[2-(Benzyl-tert-butoxycarbonyl-amino)-ethyl]-2-ethyl-hex-5-ynoic acid methyl ester 
• 189952-82-7 (1R,5S,12S)-N-benzyloxycarbonyl-12-ethyl-3-oxo-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole 
• 189952-76-9 Benzyl-[(S)-3-(1-formyl-propyl)-hex-5-ynyl]-carbamic acid tert-butyl ester 
• 86533-27-9 Ulein-N^b-oxid 
• 19046-20-9 1,13-Dihydro-ulein 
• 99612-57-4 1,13-Dihydroulein-N^b-oxid 
• 917-54-4 methyllithium 
• 2825-08-3 (+)-dasycarpidone 

Downstream Products

• 19046-20-9 1,13-Dihydro-ulein 
• 86533-27-9 Ulein-N^b-oxid 

Relevant articles and documents

Two-Carbon Ring Expansion of Cyclobutanols to Cyclohexenones Enabled by Indole Radical Cation Intermediate: Development and Application to a Total Synthesis of Uleine

A single-electron transfer (SET) oxidation of indole or benzo[b]thiophene to a radical cation reverses the intrinsic polarity of these π-excessive bicyclic heteroarenes. Here we report an oxidative two-carbon homologation of cyclobutanols to cyclohexenones under a visible-light photoredox catalysis. 1-(Indol-2-yl)cyclobutan-1-ols are converted to 2,3,4,9-tetrahydro-1H-carbazol-1-ones, important structural motifs found in alkaloids and pharmaceuticals, with a broad substrate scope. A mechanistic study suggests that the reaction is initiated by an SET from an indole to an excited acridinium salt to generate the radical cation, which is followed by two consecutive 1,2-alkyl migrations and a rearomatization. Benzo[b]thiophene-substituted cyclobutanols are similarly converted to 2,3-dihydrodibenzo[b,d]thiophen-4(1H)-ones. A total synthesis of (±)-uleine featuring this ring-expansion process is documented.

Palladium-Catalyzed Ullmann Cross-Coupling/Tandem Reductive Cyclization Route to Key Members of the Uleine Alkaloid Family

The trisubstituted cyclohexenone 12, generated through a palladium-catalyzed Ullmann cross-coupling reaction between o-iodonitrobenzene and a 4,5-trans-disubstituted 2-iodo-2-cyclohexen-1-one, engaged in a tandem reductive cyclization process upon exposur

A New Cationic Domino Process to (±)-Uleine

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