Decahydroquinoline

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Structural formula
Structure of decahydroquinoline
General
Surname Decahydroquinoline
Molecular formula C 9 H 17 N
Brief description

colorless solid

External identifiers / databases
CAS number
  • 2051-28-7 (mixture of isomers)
  • 767-92-0 ( trans isomer)
  • 10343-99-4 ( cis isomer)
EC number 218-116-7
ECHA InfoCard 100.016.470
PubChem 92911
ChemSpider 83872
Wikidata Q1181702
properties
Molar mass 139.24 g mol −1
Physical state

firmly

density

0.93 g cm −3 (mixture of isomers, 20 ° C)

Melting point

38–45 ° C (mixture of isomers)

boiling point

95-99 ° C (mixture of isomers at 27 h Pa )

Refractive index

1.4916

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Decahydroquinoline is a heterocyclic chemical compound. It consists of a piperidine ring with a cyclohexane ring fused in the 2- and 3-position . The carbocyclic analog of decahydroquinoline is decalin .

Stereoisomerism

Decadydroquinoline has two stereocenters , from which two diastereomeric , chiral structures result. These are the cis - trans isomers cis and trans decahydroquinoline.

Structures of cis - (left) and trans -decahydroquinoline (right)

Occurrence and representation

trans -Decahydrochinolin found as a basic structure in the frog poison pumiliotoxin C .

Decahydroquinoline may by complete hydrogenation of quinoline are made. The hydrogenation succeeds with molecular hydrogen in strong acids over a platinum catalyst . Initially, only the benzene ring is hydrogenated and, after a longer reaction time, complete hydrogenation to decahydroquinoline.

Individual evidence

  1. ↑ Data sheet Decahydroquinoline from Acros, accessed on July 18, 2010.
  2. ↑ a b c d e f data sheet Decahydroquinoline, mixture of cis and trans from Sigma-Aldrich , accessed on March 24, 2011 ( PDF ).
  3. ↑ External identifiers of or database links to cis-decahydroquinoline : CAS number: 10343-99-4, EC number: 233-752-5, ECHA InfoCard: 100.030.671 , PubChem : 66313 , ChemSpider : 5362372 , Wikidata : Q82861725 .
  4. ↑ External identifiers or database links for trans-decahydroquinoline : CAS number: 767-92-0, EC number: 212-189-9, ECHA InfoCard: 100.011.081 , PubChem : 66078 , ChemSpider : 59468 , Wikidata : Q63398679 .
  5. ↑ GL Patrick: Synthesis of (±) - [4aα, 4bβ, 10bβ, 12aα] -9-halogeno-2-methyl-1,2,3,4,4a, 4b, 5,6,10b, 11,12, 12a-dodecahydronaphtho [2,1-f] isoquinolines , in: J. Chem. Soc., Perkin Trans. 1 1995 , 1273-1279; doi : 10.1039 / P19950001273 .
  6. ↑ JA Joules, K. Mills: Heterocyclic Chemistry , 5th Edition, pp. 177-199, Blackwell Publishing, Chichester, 2010, ISBN 978-1-4051-9365-8 .