20316-18-1

Basic information

• Product Name: (4aR,12R)-2,3,4,4aβ,5,6-Hexahydro-12-methyl-1H-5β,10bβ-propano-1,7-phenanthroline
• Synonyms: (4aR,12R)-2,3,4,4aβ,5,6-Hexahydro-12-methyl-1H-5β,10bβ-propano-1,7-phenanthroline;Lycodine
• CAS NO: 20316-18-1
• Molecular Formula: C₁₆H₂₂N₂
• Molecular Weight: 242.35928
• Mol File: 20316-18-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 118-119°
• Boiling Point: 372.6°Cat760mmHg
• Flash Point: 179.1°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 9.51E-06mmHg at 25°C
• Refractive Index: 1.588
• PKA: 3.97, 8.08(at 25℃)
• CAS DataBase Reference: (4aR,12R)-2,3,4,4aβ,5,6-Hexahydro-12-methyl-1H-5β,10bβ-propano-1,7-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: (4aR,12R)-2,3,4,4aβ,5,6-Hexahydro-12-methyl-1H-5β,10bβ-propano-1,7-phenanthroline(20316-18-1)
• EPA Substance Registry System: (4aR,12R)-2,3,4,4aβ,5,6-Hexahydro-12-methyl-1H-5β,10bβ-propano-1,7-phenanthroline(20316-18-1)

Safety Data

• Hazardous Substances Data: 20316-18-1(Hazardous Substances Data)

Usage

Description

One of the numerous alkaloids obtained from the various Lycopodium species, this base has been found in L. annotinurn L. and L. fawcettii. It forms colourless crystals and has [α]D - 10° ± 2° (c 1.01, EtOH). One of the nitrogen atoms is present in a pyridine ring, the other being in the form of an imino group. The picrate is obtained as prisms from MeOH and has m.p. 229-233°C.

References

Anet, Eves., Can. J. Chern., 36,902 (1958) Anet, Rao., Tetrahedron Lett., No. 20, 9 (1960) Burnell et al., Can. J. Chern., 41, 3091 (1963)

InChI:InChI=1/C16H22N2/c1-11-8-12-9-15-14(5-2-6-17-15)16(10-11)13(12)4-3-7-18-16/h2,5-6,11-13,18H,3-4,7-10H2,1H3/t11-,12-,13-,16+/m1/s1

Upstream product

• 1438285-31-4 (R)-2-(3-azidopropyl)-5-methylcyclohex-2-enone 
• 90528-94-2 (-)-(R)-5-methyl-2-allyl-2-cyclohexenone 
• 1225450-38-3 Boc-lycodine 

Relevant articles and documents

One-Carbon Insertion and Polarity Inversion Enabled a Pyrrole Strategy to the Total Syntheses of Pyridine-Containing Lycopodium Alkaloids: Complanadine A and Lycodine

Complanadine A and lycodine are representative members of the Lycopodium alkaloids with a characteristic pyridine-containing tetracyclic skeleton. Complanadine A has demonstrated promising neurotrophic activity and potential for persistent pain management. Herein we report a pyrrole strategy enabled by one-carbon insertion and polarity inversion for concise total syntheses of complanadine A and lycodine. The use of a pyrrole as the pyridine precursor allowed the rapid construction of their tetracyclic skeleton via a one-pot Staudinger reduction, amine-ketone condensation, and Mannich-type cyclization. The pyrrole group was then converted to the desired pyridine by the Ciamician-Dennstedt rearrangement via a one-carbon insertion process, which also simultaneously introduced a chloride at C3 for the next C-H arylation. Other key steps include a direct anti-Markovnikov hydroazidation, a Mukaiyama-Michael addition, and a Paal-Knorr pyrrole synthesis. Lycodine and complanadine A were prepared in 8 and 11 steps, respectively, from a readily available known compound.

Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2

The first biological target for the natural product complanadine A has been determined. The pseudosymmetric alkaloid functions as a selective agonist for the Mas-related G protein-coupled receptor X2 (MrgprX2), a G protein-coupled receptor that is highly expressed in neurons. Given the potential of MrgprX2 to function as a modulator of pain, complanadine A represents a new chemical probe to selectively interrogate the physiological function of MrgprX2 as well as a potential lead for the development of antihyperalgesics for the treatment of persistent pain. While complanadine A possess agonistic activity the related natural product lycodine, representing half of complanadine A, lacks activity providing a cursory description of the structural requirements for agonistic activity.

Syntheses of (+)-complanadine A and lycodine derivatives by regioselective [2 + 2 + 2] cycloadditions

The dimeric alkaloid complanadine A has shown promise in regenerative science, promoting neuronal growth by inducing the secretion of growth factors from glial cells. Through the use of tandem, cobalt-mediated [2 + 2 + 2] cycloaddition reactions, two synthetic routes have been developed with different sequences for the formation of the unsymmetric bipyridyl core. The regioselective formation of each of the pyridines was achieved based on the inherent selectivity of the molecules or by reversing the regioselectivity through the addition of Lewis bases. This strategy has been successfully employed to provide laboratory access to complanadine A as well as structurally related compounds possessing the lycodine core.