羽扇豆鹼

羽扇豆鹼
	IUPAC名; [(1R,9aR)-Octahydro-2H-quinolizin-1-yl]methane
識別
CAS號	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
性質
化學式	C10H19NO
摩爾質量	169.26 g·mol−1
熔點	68—69 °C（154—156 °F；341—342 K）
沸點	269—270 °C（516—518 °F；542—543 K）
危險性
	GHS危險性符號;
GHS提示詞	Warning
H-術語	H302, H312, H332
P-術語	P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

羽扇豆鹼（英語：lupinine），即(1R,9aR)-八氫-2H-喹嗪-1-甲醇，是一種有機化合物，化學式為C₁₀H₁₉NO。它可以三烷基矽氧基呋喃為原料合成得到。^[1]它和甲磺酰氯在三乙胺存在下於二氯甲烷中反應，可以得到羽扇豆鹼甲磺酸酯。^[2]它和碘甲烷在丙酮中反應，可以得到N-甲基羽扇豆鹼鎓碘化物。^[3]

參考文獻

^ 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.

[1]

[2]

[3]