14912-31-3

Basic information

• Product Name: (+)-Fawcettidine
• Synonyms: (+)-Fawcettidine;(1R)-2,3,4,4aβ,6,6aβ,7,8-Octahydro-8β-methyl-1β,9bβ-propano-5H-indeno[7,1-bc]azepin-5-one;Fawcettidine
• CAS NO: 14912-31-3
• Molecular Formula: C16H23NO
• Molecular Weight: 245.35992
• Mol File: 14912-31-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 407.1°Cat760mmHg
• Flash Point: 159.5°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 7.75E-07mmHg at 25°C
• Refractive Index: 1.576
• PKA: 8.42±0.40(Predicted)
• CAS DataBase Reference: (+)-Fawcettidine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Fawcettidine(14912-31-3)
• EPA Substance Registry System: (+)-Fawcettidine(14912-31-3)

Safety Data

• Hazardous Substances Data: 14912-31-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H23NO/c1-11-8-12-10-14(18)13-4-2-6-17-7-3-5-16(12,13)15(17)9-11/h9,11-13H,2-8,10H2,1H3/t11-,12+,13-,16+/m1/s1

Upstream product

• 481048-37-7 (+)-lycoposerramine Q 
• 78-79-5 isoprene 
• 58274-64-9 (E)-trimethyl((3-methylbuta-1,3-dien-1-yl)oxy)silane 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 1375195-74-6 (3a'R,7a'S)-5'-methyl-2',3',3a',4',7',7a'-hexahydrospiro-[[1,3]dioxolane-2,1'-indene] 

Relevant articles and documents

Divergent and efficient syntheses of the Lycopodium alkaloids (-)-Lycojaponicumin C, (-)-8-deoxyserratinine, (+)-fawcettimine, and (+)-fawcettidine

Four from one: The four title alkaloids (structures shown in blue box) have been synthesized by using a common versatile intermediate with a 6/5/5 tricyclic skeleton. This tricyclic intermediate could be easily assembled by using an intramolecular carbene addition/cyclization and a Dieckmann condensation/Tsuji-Trost allylation as key steps. Copyright

Concise unified access to (-)-8-deoxy-13-dehydroserratinine, (+)-fawcettimine, (+)-fawcettidine, and (-)-8-deoxyserratinine using a direct intramolecular reductive coupling

A short, scalable, and collective total synthesis of four fawcettimine-type Lycopodium alkaloids in eight or nine steps is disclosed. A dense multi-small-ring spiro-α-aminocyclopentanone successfully served as the key intermediate, which was directly acce

Collective synthesis of lycopodium alkaloids and tautomer locking strategy for the total synthesis of (-)-lycojapodine A

The collective total synthesis of Lycopodium alkaloids (+)-fawcettimine (1), (+)-fawcettidine (2), (+)-alopecuridine (4), (-)-lycojapodine A (6), and (-)-8-deoxyserratinine (7) has been accomplished from a common precursor (15) based on a highly concise route inspired by the proposed biosynthesis of the fawcettimine- and serratinine-type alkaloids. An intramolecular C-alkylation enabled efficient installation of the challenging spiro quaternary carbon center and the aza-cyclononane ring. The preparation of the tricyclic skeleton as well as the establishment of the correct relative stereochemistry of the oxa-quaternary center were achieved by hydroxyl-directed SmI2- mediated pinacol couplings. An unprecedented tandem transannular N-alkylation and removal of a Boc group was discovered to realize a biosynthesis-inspired process to furnish the desired tetracyclic skeleton. Of particular note is the unique and crucial tautomer locking strategy employed to complete the enantioselective total synthesis of (-)-lycojapodine A (6). The central step in this synthesis is the late-stage hypervalent iodine oxidant (IBX or Dess-Martin periodinane)/TFA-mediated tandem process, which constructed the previously unknown carbinolamine lactone motif and enabled a biomimetic transformation to generate (-)-lycojapodine A (6) in a single operation.