485-57-4

Basic information

• Product Name: (-)-Coccinine
• Synonyms: (2β)-2-O-Methylpancracine;(6aS)-5,6a,7,8,9,11-Hexahydro-6α,11α-methano-9β-methoxy-6H-1,3-benzodioxolo[5,6-c][1]benzazepin-8β-ol;Coccinine【alkaloid】;O2-Methyl-2-epipancracine
• CAS NO: 485-57-4
• Molecular Formula: C₁₇H₁₉NO₄
• Molecular Weight: 301.33706
• Mol File: 485-57-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Coccinine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Coccinine(485-57-4)
• EPA Substance Registry System: (-)-Coccinine(485-57-4)

Safety Data

• Hazardous Substances Data: 485-57-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 139025-52-8 C₁₆H₁₅NO₃ 
• 139025-52-8 (2S*,3R*,4aR*,11S*)-5,11a-cis-11,11a-syn-2,3-epoxy-Δ^1(11a)-8,9-(methylenedioxy)-5,11-methanomorphanthridine 
• 139025-49-3 (+/-)-O-benzylcoccinine 
• 139025-49-3 (+/-)-O-benzylcoccinine 
• 139025-49-3 (+/-)-O-benzylmontanine 
• 17680-04-5 (3,4-methylenedioxy)phenylmagnesium bromide 
• 139025-41-5 (1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenecarboxylic acid 
• 139025-42-6 (1R*,2S*)-2-<3',4'-(methylenedioxy)benzoyl>-4-cyclohexenyl-N-tosylamide 
• 144609-79-0 (2S*,3R*,4aR*,11S*,11aR*)-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine 
• 139883-52-6 (1R*,2R*,4S*,5R*)-4,5-diacetoxy-2-<1'-<3'',4''-(methylenedioxy)phenyl>vinyl>-1-cyclohexyl-N-tosylamide 
• 139025-45-9 (2S*,3R*,4aR*,11S*,11aR*)-2,3-O-benzylidene-2,3-dihydroxy-11-(hydroxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine 
• 139025-44-8 (1R*,1'S*,2R*,4S*,5R*)-2-<2'-acetoxy-1'-<3'',4''-(methylenedioxy)phenyl>ethyl>-4,5-diacetoxy-1-cyclohexyl-N-tosylamide 
• 144609-78-9 (2S*,3R*,4aR*,11S*,11aR*)-2,3-diacetoxy-11-(acetoxymethyl)-8,9-(methylenedioxy)-5-tosylmorphanthridine 

Downstream Products

• 606-51-9 O-Methyl-coccinin 

Relevant articles and documents

Bioinspired total synthesis of montanine-type amaryllidaceae alkaloids

Finding a common path: A synthetic strategy inspired by the proposed biogenesis of the montanine-type alkaloids enabled the concise asymmetric synthesis of these compounds in a divergent fashion on the basis of an unprecedented tandem oxidative dearomatization/intramolecular aza-Michael addition as the key step. This bioinspired approach revealed a chemical connection between the cherylline- and montanine-type alkaloids (see scheme). Copyright

A FIRST TOTAL SYNTHESIS OF MONTANINE-TYPE AMARYLLIDACEAE ALKALOIDS, (+/-)-COCCININE, (+/-)-MONTANINE, AND (+/-)-PANCRACINE

Montanine-type Amaryllidaceae alkaloids, (+/-)-coccinine (1), (+/-)-montanine (2), and (+/-)-pancracine (3) were synthesized starting from (+/-)-1,2-cis-2-(3,4-methylenedioxybenzoyl)cyclohex-4-enecarboxylic acid (6) via (+/-)-2,3-cis-3-benzyloxy-2-hydroxy