6519-27-3

Basic information

• Product Name: 16-epi-isositsirikine
• Synonyms: 16-epi-isositsirikine;(16R,19E)-19,20-Didehydro-17-hydroxycorynan-16-carboxylic acid methyl ester;Isositsirikine;(16R)-E-Isositsirikine;NSC 282700;NSC 338932;Rhazimanine
• CAS NO: 6519-27-3
• Molecular Formula: C21H26N2O3
• Molecular Weight: 354.45
• Mol File: 6519-27-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 263.5℃
• Boiling Point: 558.9°C at 760 mmHg
• Flash Point: 291.8°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 2.49E-13mmHg at 25°C
• Refractive Index: 1.643
• PKA: 14.29±0.10(Predicted)
• CAS DataBase Reference: 16-epi-isositsirikine(CAS DataBase Reference)
• NIST Chemistry Reference: 16-epi-isositsirikine(6519-27-3)
• EPA Substance Registry System: 16-epi-isositsirikine(6519-27-3)

Safety Data

• Hazardous Substances Data: 6519-27-3(Hazardous Substances Data)

Usage

Description

An amorphous alkaloid found in Vinca rosea L., this laevorotatory base has [α]25D - 20° (CHCI3). In EtOH, the ultraviolet spectrum has absorption maxima at 224, 283 and 291 m/J.. The alkaloid forms a hemisulphate, m.p. 263.5°C and an amorphous O-acetate. The picrate is obtained in the form of brilliant yellow needles when crystallized from MeOH, m.p. 216°C.

References

Kutney, Brown., Tetrahedron, 22,321 (1966)

InChI:InChI=1/C21H26N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,16-17,19,22,24H,8-12H2,1-2H3/b13-3-/t16-,17-,19-/m0/s1

Upstream product

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Relevant articles and documents

Total Syntheses of Naucleamides A-C and E, Geissoschizine, Geissoschizol, (E)-Isositsirikine, and 16-epi-(E)-Isositsirikine

A divergent approach for the enantioselective total synthesis of eight monoterpenoid indole alkaloids was developed. The approach allows the first total syntheses of naucleamides A-C and E in only 6-8 steps and also enables the efficient synthesis of geissoschizine, geissoschizol, (E)-isositsirikine, and 16-epi-(E)-isositsirikine in 10-11 steps from commercially available crotonic aldehyde. The synthesis features a one-pot organocatalyzed asymmetric Michael addition/Pictet-Spengler reaction. Notably, biomimetic synthesis of naucleamide E was achieved by oxidative cyclization of naucleamide A.

ALKALOIDS FROM RHAZYA STRICTA

Chemical investigations of roots and leaves of Rhazya stricta have resulted in the isolation of the new indole alkaloids, 16R-19,20-E-isositsirikine acetate, leepacine and dihydroeburnamenine, along with six known alkaloids.Among these, (-)-16R,21R-O-methyleburnamine, 2-ethyl-3-indole, (20S)-19,20-dihydrocondylocarpine and N-acetylaspidospermidine have been isolated for the first time from R. stricta.Spectral studies on (+)-21S-eburnamenine and the glycoalkaloid strictosamide have also been undertaken. --- Key Word Index: Rhazya stricta; Apocynaceae; indole alkaloide; glycoalkaloids; 13C NMR.

Preparation and H(3) Isomerization of C(15)-Substituted Deplancheine Derivatives. Synthesis of Geissoschizol and Geissoschizine

A series of indoloquinolizidines have been prepared by the two-step scheme of nucleophile addition to 1-tryptophyl-3-acylpyridinium salts or their vinylogues and subsequent, acid-catalyzed cyclization.Acid-induced hydrolysis, decarboxylation, and reduction of the resultant vinylogous urethanes has opened an approach to antirhine and yielded C(15)-substituted deplancheine derivatives.Functional group manipulation of the latter has permitted the syntheses of geissoschizol and geissoschizine.