Crinine

Crinine
Names
	IUPAC name (1S,13R,15R)-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-15-ol
	Other names Crinidine
Identifiers
CAS Number	510-67-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31437;
ChEMBL	ChEMBL1221864;
ChemSpider	353636;
KEGG	C12152;
PubChem CID	398937;
	InChI InChI=1S/C16H17NO3/c18-11-1-2-16-3-4-17(15(16)6-11)8-10-5-13-14(7-12(10)16)20-9-19-13/h1-2,5,7,11,15,18H,3-4,6,8-9H2/t11-,15+,16+/m0/s1 Key: RPAORVSEYNOMBR-IUIKQTSFSA-N;
	SMILES C1CN2CC3=CC4=C(C=C3[C@]15[C@H]2C[C@H](C=C5)O)OCO4;
Properties
Chemical formula	C16H17NO3
Molar mass	271.316 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Crinine in an alkaloid found in a variety of plants including many species in the family Amaryllidaceae. It was first isolated and characterized in the 1950s as a constituent of several plants in the genus Crinum, from which it derives its name.^[1]^[2]^[3]

Several laboratory syntheses of crinine have been reported.^[4]^[5]^[6]^[7]

Related compounds

There are many alkaloids with a chemical structure similar to crinine and they are generally referred to as crinine-type alkaloids. As of 2020, there were at least 85 known crinine-type alkaloids.^[8]

Chemical structures of selected crinine-type alkaloids

References

↑ Boit, Hans-G. (1954). "Über die Alkaloide von Nerine sarniensis, Crinum moorei, Hippeastrum vittatum und Clivia miniata (VI. Mitteil. über Amaryllidaceen-Alkaloide)". Chemische Berichte. 87 (11): 1704–1707. doi:10.1002/cber.19540871115.
↑ Mason, L. H.; Puschett, E. R.; Wildman, W. C. (1955). "Alkaloids of the Amaryllidaceae. IV. Crystalline Alkaloids of Ammocharis coranica (Ker-Gawl.) Herb., Brunsvigia rosea (Lam.) Hannibal and Two Crinum Species". Journal of the American Chemical Society. 77 (5): 1253–1256. Bibcode:1955JAChS..77.1253M. doi:10.1021/ja01610a046.
↑ Boit, Hans-G.; Ehmke, Horst (1955). "Alkaloide von Sprekelia formosissima, Galanthus elwesii, Zephyranthes candida und Crinum powellii (VIII. Mitteil. über Amaryllidaceen-Alkaloide¹⁾)". Chemische Berichte. 88 (10): 1590–1594. doi:10.1002/cber.19550881019.
↑ Muxfeldt, Hans; Schneider, Richard S.; Mooberry, Jared B. (1966). "A Total Synthesis of (±)-Crinine". Journal of the American Chemical Society. 88 (15): 3670–3671. Bibcode:1966JAChS..88.3670M. doi:10.1021/ja00967a052.
↑ Martin, Stephen F.; Campbell, Carlton L. (1988). "Total syntheses of (.+-.)-crinine and (.+-.)-buphanisine". The Journal of Organic Chemistry. 53 (14): 3184–3190. doi:10.1021/jo00249a011.
↑ Whitlock, Howard W.; Smith, Gary Lee. (1967). "Total synthesis of DL-crinine". Journal of the American Chemical Society. 89 (14): 3600–3606. Bibcode:1967JAChS..89.3600W. doi:10.1021/ja00990a045.
↑ Bru, Claire; Guillou, Catherine (2006). "Total syntheses of crinine and related alkaloids". Tetrahedron. 62 (38): 9043–9048. doi:10.1016/j.tet.2006.07.005.
↑ Strahil Berkov, Jaume Bastida (2020). "Chemodiversity, chemotaxonomy and chemoecology of Amaryllidaceae alkaloids". The Alkaloids: Chemistry and Biology.

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[1] Boit, Hans-G. (1954). "Über die Alkaloide von Nerine sarniensis, Crinum moorei, Hippeastrum vittatum und Clivia miniata (VI. Mitteil. über Amaryllidaceen-Alkaloide)". Chemische Berichte. 87 (11): 1704–1707. doi:10.1002/cber.19540871115.

[2] Mason, L. H.; Puschett, E. R.; Wildman, W. C. (1955). "Alkaloids of the Amaryllidaceae. IV. Crystalline Alkaloids of Ammocharis coranica (Ker-Gawl.) Herb., Brunsvigia rosea (Lam.) Hannibal and Two Crinum Species". Journal of the American Chemical Society. 77 (5): 1253–1256. Bibcode:1955JAChS..77.1253M. doi:10.1021/ja01610a046.

[3] Boit, Hans-G.; Ehmke, Horst (1955). "Alkaloide von Sprekelia formosissima, Galanthus elwesii, Zephyranthes candida und Crinum powellii (VIII. Mitteil. über Amaryllidaceen-Alkaloide¹⁾)". Chemische Berichte. 88 (10): 1590–1594. doi:10.1002/cber.19550881019.

[4] Muxfeldt, Hans; Schneider, Richard S.; Mooberry, Jared B. (1966). "A Total Synthesis of (±)-Crinine". Journal of the American Chemical Society. 88 (15): 3670–3671. Bibcode:1966JAChS..88.3670M. doi:10.1021/ja00967a052.

[5] Martin, Stephen F.; Campbell, Carlton L. (1988). "Total syntheses of (.+-.)-crinine and (.+-.)-buphanisine". The Journal of Organic Chemistry. 53 (14): 3184–3190. doi:10.1021/jo00249a011.

[6] Whitlock, Howard W.; Smith, Gary Lee. (1967). "Total synthesis of DL-crinine". Journal of the American Chemical Society. 89 (14): 3600–3606. Bibcode:1967JAChS..89.3600W. doi:10.1021/ja00990a045.

[7] Bru, Claire; Guillou, Catherine (2006). "Total syntheses of crinine and related alkaloids". Tetrahedron. 62 (38): 9043–9048. doi:10.1016/j.tet.2006.07.005.

[8] Strahil Berkov, Jaume Bastida (2020). "Chemodiversity, chemotaxonomy and chemoecology of Amaryllidaceae alkaloids". The Alkaloids: Chemistry and Biology.

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Related compounds

References