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去甲氧基去乙酰基白坚木碱

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去甲氧基去乙酰基白坚木碱
IUPAC名
(3aR,10bR)-3aβ-Ethyl-2,3,3a,4,5,5aα,6,11,12,13aβ-decahydro-1H-indolizino[8,1-cd]carbazole
识别
CAS号 2912-09-6（+）  checkY
32975-45-4（-）  checkY
7689-02-3（±）  checkY
PubChem 6857472
ChemSpider 5256809
SMILES
 
  • CC[C@]12CCCN3[C@H]1[C@]4(CC3)c5ccccc5N[C@@H]4CC2
InChI
 
  • 1/C19H26N2/c1-2-18-9-5-12-21-13-11-19(17(18)21)14-6-3-4-7-15(14)20-16(19)8-10-18/h3-4,6-7,16-17,20H,2,5,8-13H2,1H3/t16-,17-,18-,19-/m1/s1
InChIKey YAAIPCQYJYPITK-NCXUSEDFBY
ChEBI 38486
性质
化学式 C19H26N2
摩尔质量 282.42 g·mol−1
外观 浅黄色固体（+）[1]
白色固体（-）[2]
熔点 118-120 °C（+）[1]
113-114 °C（-）[2]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

去甲氧基去乙酰基白坚木碱是从白堅木屬植物中提取出来的生物鹼，化学式为C19H26N2。[3]由于它的结构与很多重要的具有生物活性的分子相似[4] ，它是全合成的热门分子。[5][6][7][8]

参考文献

  1. ^ 1.0 1.1 Ganesh Pandey, Shiva Kumar Burugu, and Pushpendra Singh. Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine. Org. Lett. 2016, 18, 7, 1558–1561. doi:10.1021/acs.orglett.6b00374.
  2. ^ 2.0 2.1 Marius Mewald, Jonathan William Medley, Mohammad Movassaghi. Concise and Enantioselective Total Synthesis of (−)-Mehranine, (−)-Methylenebismehranine, and Related Aspidosperma Alkaloids. Angew Chem Int Ed. 2014. 53 (43). doi:10.1002/anie.201405609
  3. ^ Deutsch, Harold F.; Evenson, Merle A.; Drescher, Peter; Sparwasser, Christoph; Madsen, Paul O. Isolation and biological activity of aspidospermine and quebrachamine from an Aspidosperma tree source. Journal of Pharmaceutical and Biomedical Analysis. October 1994, 12 (10): 1283–1287. PMID 7841224. doi:10.1016/0731-7085(94)00066-2. 
  4. ^ Anagnostaki, Elissavet E.; Zografos, Alexandros L. "Common synthetic scaffolds" in the synthesis of structurally diverse natural products. Chemical Society Reviews. 2012, 41 (17): 5613–25. PMID 22782134. doi:10.1039/c2cs35080g. 
  5. ^ Marino, Joseph P.; Rubio, Maria B.; Cao, Ganfeng; de Dios, Alfonso. Total Synthesis of (+)-Aspidospermidine: A New Strategy for the Enantiospecific Synthesis of Aspidosperma Alkaloids. Journal of the American Chemical Society. November 2002, 124 (45): 13398–13399. PMID 12418888. doi:10.1021/ja026357f. 
  6. ^ Jones, Spencer B.; Simmons, Bryon; Mastracchio, Anthony; MacMillan, David W. C. Collective synthesis of natural products by means of organocascade catalysis. Nature. 13 July 2011, 475 (7355): 183–188. PMC 3439143 可免费查阅. PMID 21753848. doi:10.1038/nature10232. 
  7. ^ Ma, Haichen; Xie, Xingang; Jing, Peng; Zhang, Weiwei; She, Xuegong. Concise total synthesis of (±)-aspidospermidine. Org. Biomol. Chem. 2015, 13 (18): 5255–5259. PMID 25856579. doi:10.1039/C5OB00228A. 
  8. ^ Callaghan, Owen; Lampard, Christopher; Kennedy, Alan R.; Murphy, John A. A novel total synthesis of (±)-aspidospermidine. Journal of the Chemical Society, Perkin Transactions 1. 1999, (8): 995–1002. doi:10.1039/A900335E. 
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