Lennoxamine

Lennoxamine
Identifiers
CAS Number	95530-38-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	9101496 ; 10396941 (3R)-henicos ; 9947258 (3S)-henicos ;
PubChem CID	10926251; 21771725 (3R)-henicos; 11772575 (3S)-henicos;
UNII	EKT38NF7FQ ;
CompTox Dashboard (EPA)	DTXSID20448602 ;
	InChI InChI=1S/C20H19NO5/c1-23-15-4-3-13-14-7-12-9-17-16(25-10-26-17)8-11(12)5-6-21(14)20(22)18(13)19(15)24-2/h3-4,8-9,14H,5-7,10H2,1-2H3 Key: GIVXYHGHGFITPJ-UHFFFAOYSA-N ; InChI=1/C20H19NO5/c1-23-15-4-3-13-14-7-12-9-17-16(25-10-26-17)8-11(12)5-6-21(14)20(22)18(13)19(15)24-2/h3-4,8-9,14H,5-7,10H2,1-2H3 Key: GIVXYHGHGFITPJ-UHFFFAOYAR;
	SMILES COC1=C(OC)C2=C(C=C1)C1CC3=C(CCN1C2=O)C=C1OCOC1=C3; COc1ccc2c(c1OC)C(=O)N3C2Cc4cc5c(cc4CC3)OCO5;
Properties
Chemical formula	C20H19NO5
Molar mass	353.374 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Lennoxamine is an isoindolobenzazepine alkaloid, originally isolated from the Chilean barberry, Berberis darwinii. Lennoxamine has been synthesised from 6-bromopiperonal in 9 steps;^[1]; from 3-(3,4-methylenedioxybenzylidene)-6,7-dimsthoxyphthalide in 4 or 5 steps;^[2] and from 2,3-dimethoxybenzoic acid in 8 steps.^[3]

References

^ Moody, Christopher J.; Warrellow, Graham J. (January 1987). "Synthesis of the isoindolobenzazepine alkaloid lennoxamine". Tetrahedron Letters. 28 (48): 6089–6092. doi:10.1016/s0040-4039(00)96871-0.
^ Napolitano, Elio; Spinelli, Guido; Fiaschi, Rita; Marsili, Antonio (1986). "A simple total synthesis of the isoindolobenzazepine alkaloids lennoxamine and chilenamine". Journal of the Chemical Society, Perkin Transactions 1: 785. doi:10.1039/p19860000785.
^ Couty, Sylvain; Meyer, Christophe; Cossy, Janine (January 2006). "A short synthesis of lennoxamine via ynamides". Tetrahedron Letters. 47 (5): 767–769. doi:10.1016/j.tetlet.2005.11.093.

[1] Moody, Christopher J.; Warrellow, Graham J. (January 1987). "Synthesis of the isoindolobenzazepine alkaloid lennoxamine". Tetrahedron Letters. 28 (48): 6089–6092. doi:10.1016/s0040-4039(00)96871-0.

[2] Napolitano, Elio; Spinelli, Guido; Fiaschi, Rita; Marsili, Antonio (1986). "A simple total synthesis of the isoindolobenzazepine alkaloids lennoxamine and chilenamine". Journal of the Chemical Society, Perkin Transactions 1: 785. doi:10.1039/p19860000785.

[3] Couty, Sylvain; Meyer, Christophe; Cossy, Janine (January 2006). "A short synthesis of lennoxamine via ynamides". Tetrahedron Letters. 47 (5): 767–769. doi:10.1016/j.tetlet.2005.11.093.

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