75556-13-7

Basic information

• Product Name: Hippocasine
• Synonyms: Hippocasine
• CAS NO: 75556-13-7
• Molecular Formula: C13H21N
• Molecular Weight: 191.31
• Mol File: 75556-13-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Hippocasine(CAS DataBase Reference)
• NIST Chemistry Reference: Hippocasine(75556-13-7)
• EPA Substance Registry System: Hippocasine(75556-13-7)

Safety Data

• Hazardous Substances Data: 75556-13-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Hippocasine is used as a bioactive compound for its potential applications in drug development and therapeutics. Its unique properties and ability to be modified through chemical treatment make it a promising candidate for the creation of new pharmaceutical agents.
Used in Chemical Research:
Hippocasine is used as a subject of chemical research for understanding its structure, properties, and potential applications. The study of its N-oxide formation through treatment with hydrogen peroxide can provide insights into the chemical behavior and modifications of similar compounds.
Used in Insect Defense Mechanism Studies:
Hippocasine is used in the study of insect defense mechanisms, specifically in ladybugs, to understand how they produce and utilize these bioactive compounds for protection against predators and other threats. This knowledge can contribute to the development of new defense strategies in agriculture and other fields.

References

Ayer et al., Can. J. Chem., 54, 1807 (1976)

Upstream product

• 1130-59-2 dodecahydro-9b-bora-phenalene 
• 57147-60-1 (3aα,6aα,9aα)-decahydropyrido<2,1,6-de>quinolizine-3a(1H)-carboxamide 
• 90027-00-2 (3aα,6aα,9aβ)-(+/-)-decahydropyrido<2,1,6-de>quinolizine-3a(1H)-carboxamide 
• 90025-88-0 (3aS,6aS,9aR)-Decahydro-pyrido[2,1,6-de]quinolizine-3a-carbonitrile 
• 89959-61-5 cis-(+/-)-1,2,3,3a,4,5,6,6a,7,8-decahydropyrido<2,1,6-de>quinolizine 
• 75509-50-1 trans-(+/-)-1,2,3,3a,4,5,6,6a,7,8-decahydropyrido<2,1,6-de>quinolizine 
• 90025-92-6 (3aα,6aβ,10β)-(+/-)-1,2,3,3a,4,5,6,6a,7,8-decahydro-10-methylpyrido<2,1,6-de>quinolizinium fluorosulfate 
• 90025-94-8 C₁₃H₂₂N⁽¹⁺⁾*FO₃S^(1-) 
• 89959-62-6 Dodecahydro-pyrido[2,1,6-de]quinolizine 10-oxide 
• 61714-12-3 (+/-)-trans-13-azabicyclo<7.3.1>tridecan-5-ol 
• 57147-55-4 1,5,9-cyclododecanetrione 
• 57147-57-6 (3aα,6aα,9aα)-dodecahydropyrido<2,1,6-de>quinolizine 
• 57194-67-9 (3aα,6aα,9aβ)-dodecahydropyrido<2,1,6-de>quinolizine 
• 75509-51-2 (3aR,6aR,9aR)-2-[1-Dimethylamino-meth-(Z)-ylidene]-decahydro-pyrido[2,1,6-de]quinolizin-1-one 

Downstream Products

• 38211-56-2 precoccinelline 
• 34290-97-6 coccinelline 

Relevant articles and documents

New strategy for the synthesis of ladybird beetle azaphenalene alkaloids using a combination of allylboration and intramolecular metathesis. Total synthesis of (±)-Hippocasine and (±)-epi-Hippodamine

A new strategy for assembly a tricyclic skeleton of ladybirds azaphenalene alkaloids (coccinellides) was developed based on the combination of allylboration reaction and intramolecular metathesis. The first key step is the 1,2-organolithiation of 4-picoline with (4,4-dieth-oxybutyl)lithium with subsequent reductive allylation with triallylborane leading to trans-2-allyl-6-(4,4-diethoxybutyl)-4-methyl-1,2,3,6-tetrahydropyridine. The 4,4-diethoxybutyl substituent was further converted to 4-acetoxy-5-hexenyl in four steps, then, the product obtained was involved in the second key step, the intramolecular allylic amination upon treatment with a [Pd] or an [Ir] catalyst giving diastereomeric bicyclic terminal dienes (μ1: 1), which were separated by chromatography. The stereochemistry of one of the dienes is the same as that in alkaloid Hippocasine. The third key step (the intramolecular metathesis reaction) includes the final assembly of the azaphenalene system. The tricyclic derivative obtained contains two differently substituted C=C bonds, selective hydrogenation of one of which (Pd/C) leads to (±)-Hippocasine, whereas exhaustive hydrogenation gives (±)-epi-Hippodamine.

Stereo- and Regioselective Total Synthesis of the Hydropyridoquinolizine Ladybug Defensive Alkaloids

The stereo- and regioselective syntheses of the ladybug defensive alkaloids coccinelline (1), precoccinelline (2), (+/-)-hippodamine (3), (+/-)-convergine (4), (+/-)-hippocasine (5), (+/-)-hippocasine oxide (6), myrrhine (7), (+/-)-propyleine (8), and (+/-)-isopropyleine (9) are described starting from perhydroboraphenalene.

SYNTHESIS OF THE LADYBUG DEFENSIVE AGENTS (+-)-HIPPODAMINE, (+-)-CONVERGINE, (+-)-HIPPOCASINE AND (+-)-HIPPOCASINE OXIDE

The total syntheses of the ladybug defensive agents (+-)-hippoidamine, (+-)-convergine, (+-)-hippocasine, and (+-)-hippocasine oxide are described starting from perhydroboraphenalene.