羽扇豆碱

羽扇豆碱
	IUPAC名; [(1R,9aR)-Octahydro-2H-quinolizin-1-yl]methane
识别
CAS号	486-70-4
PubChem	91461
ChemSpider	82587
SMILES	OC[C@H]1[C@@H]2N(CCC1)CCCC2;
InChI	1/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1;
InChIKey	HDVAWXXJVMJBAR-VHSXEESVBK
3DMet	B04202
ChEBI	28012
KEGG	C10773
性质
化学式	C10H19NO
摩尔质量	169.26 g·mol−1
熔点	68—69 °C（154—156 °F；341—342 K）
沸点	269—270 °C（516—518 °F；542—543 K）
危险性
	GHS危险性符号;
GHS提示词	Warning
H-术语	H302, H312, H332
P-术语	P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

羽扇豆碱（英语：lupinine），即(1R,9aR)-八氢-2H-喹嗪-1-甲醇，是一种有机化合物，化学式为C₁₀H₁₉NO。它可以三烷基硅氧基呋喃为原料合成得到。^[1]它和甲磺酰氯在三乙胺存在下于二氯甲烷中反应，可以得到羽扇豆碱甲磺酸酯。^[2]它和碘甲烷在丙酮中反应，可以得到N-甲基羽扇豆碱𬭩碘化物。^[3]

参考文献

^ Santos, Leonardo; Mirabal-Gallardo, Yaneris; Shankaraiah, Nagula; Simirgiotis, Mario. Short Total Synthesis of (-)-Lupinine and (-)-Epiquinamide by Double Mitsunobu Reaction. Synthesis (Georg Thieme Verlag KG). 2010-12-08, 2011 (01): 51–56. ISSN 0039-7881. doi:10.1055/s-0030-1258356.
^ Nurmaganbetov, Zhangeldy S.; Savelyev, Viktor A.; Gatilov, Yurii V.; Nurkenov, Oralgazy A.; Seidakhmetova, Roza B.; Shulgau, Zarina T.; Mukusheva, Gulim K.; Fazylov, Serik D.; Shults, Elvira E. Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine. Chemistry of Heterocyclic Compounds (Springer Science and Business Media LLC). 2021, 57 (9): 911–919. ISSN 0009-3122. doi:10.1007/s10593-021-03000-7.
^ Fitch, Richard W.; Sturgeon, Gordon D.; Patel, Shaun R.; Spande, Thomas F.; Garraffo, H. Martin; Daly, John W.; Blaauw, Richard H. Epiquinamide: A Poison That Wasn’t from a Frog That Was. Journal of Natural Products (American Chemical Society (ACS)). 2009-02-06, 72 (2): 243–247. ISSN 0163-3864. doi:10.1021/np8005452.

[1] Santos, Leonardo; Mirabal-Gallardo, Yaneris; Shankaraiah, Nagula; Simirgiotis, Mario. Short Total Synthesis of (-)-Lupinine and (-)-Epiquinamide by Double Mitsunobu Reaction. Synthesis (Georg Thieme Verlag KG). 2010-12-08, 2011 (01): 51–56. ISSN 0039-7881. doi:10.1055/s-0030-1258356.

[2] Nurmaganbetov, Zhangeldy S.; Savelyev, Viktor A.; Gatilov, Yurii V.; Nurkenov, Oralgazy A.; Seidakhmetova, Roza B.; Shulgau, Zarina T.; Mukusheva, Gulim K.; Fazylov, Serik D.; Shults, Elvira E. Synthesis and analgesic activity of 1-[(1,2,3-triazol-1-yl)methyl]quinolizines based on the alkaloid lupinine. Chemistry of Heterocyclic Compounds (Springer Science and Business Media LLC). 2021, 57 (9): 911–919. ISSN 0009-3122. doi:10.1007/s10593-021-03000-7.

[3] Fitch, Richard W.; Sturgeon, Gordon D.; Patel, Shaun R.; Spande, Thomas F.; Garraffo, H. Martin; Daly, John W.; Blaauw, Richard H. Epiquinamide: A Poison That Wasn’t from a Frog That Was. Journal of Natural Products (American Chemical Society (ACS)). 2009-02-06, 72 (2): 243–247. ISSN 0163-3864. doi:10.1021/np8005452.

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