643-20-9 Usage
Description
Hexahydro-1H-pyrrolizine is a bicyclic organonitrogen heterocyclic compound that consists of two ortho-fused pyrrolidine rings sharing a common nitrogen atom. This unique structure endows it with various chemical and biological properties, making it a versatile molecule for different applications.
Uses
Used in Pharmaceutical Industry:
Hexahydro-1H-pyrrolizine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique bicyclic structure allows for the development of drugs with specific therapeutic properties, such as analgesics, anti-inflammatory agents, and antidepressants.
Used in Chemical Synthesis:
Hexahydro-1H-pyrrolizine serves as a valuable building block in the synthesis of complex organic molecules. Its ability to form stable bonds with other chemical entities makes it an ideal candidate for the creation of novel compounds with potential applications in various industries.
Used in Material Science:
Hexahydro-1H-pyrrolizine can be utilized in the development of advanced materials with unique properties. Its incorporation into polymers, for instance, can lead to the creation of materials with enhanced mechanical strength, thermal stability, and chemical resistance.
Used in Agrochemical Industry:
Hexahydro-1H-pyrrolizine can be employed as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its ability to form stable complexes with other molecules can contribute to the development of more effective and environmentally friendly agrochemicals.
World Health Organization (WHO)
Plants containing pyrrolizidine alkaloids have traditionally been
made into teas in the Caribbean and South-East Asia and several of these active
substances have been incorporated into medicines for use in treatment for a
variety of illnesses. The decision to prohibit use of these products was based on
their association with a variety of adverse effects and on their hepatotoxic and carcinogenic potential as seen in both laboratory animals and in communities that
commonly use plants containing these compounds to prepare teas and other
beverages.
Synthesis Reference(s)
Canadian Journal of Chemistry, 50, p. 1167, 1972 DOI: 10.1139/v72-184Journal of the American Chemical Society, 82, p. 1466, 1960 DOI: 10.1021/ja01491a047
Check Digit Verification of cas no
The CAS Registry Mumber 643-20-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 3 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 643-20:
(5*6)+(4*4)+(3*3)+(2*2)+(1*0)=59
59 % 10 = 9
So 643-20-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H13N/c1-3-7-4-2-6-8(7)5-1/h7H,1-6H2
643-20-9Relevant articles and documents
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Schweizer,Light
, p. 2963 (1964)
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Synthesis of indolizidine, pyrrolizidine and quinolizidine ring systems by proline-catalyzed sequential α-amination and HWE olefination of an aldehyde
Kauloorkar, Shruti Vandana,Jha, Vishwajeet,Kumar, Pradeep
, p. 18288 - 18291 (2013/10/21)
A general procedure for the synthesis of azabicyclic ring systems viz. indolizidine, pyrrolizidine and quinolizidine has been developed utilizing proline-catalyzed sequential α-amination and Horner-Wadsworth-Emmons (HWE) olefination of an aldehyde as the key step. This method can be further extended to the synthesis of various biologically active natural products containing azabicyclic ring systems.
Hydrogenation of pyrrolizin-3-ones; New routes to pyrrolizidines
Despinoy, Xavier L. M.,McNab, Hamish
experimental part, p. 4502 - 4511 (2009/12/25)
Pyrrolizin-3-ones (e.g.1) can be easily hydrogenated to their hexahydro (pyrrolizidin-3-one) derivatives in the presence of heterogeneous catalysts. Good diastereoselectivity (up to >97:3, depending on catalysts and solvent) can be achieved if the pyrroli
Stereochemistry of β-deuterium isotope effects on amine basicity
Perrin, Charles L.,Ohta, Brian K.,Kuperman, Joshua,Liberman, Jordan,Erdelyi, Mate
, p. 9641 - 9647 (2007/10/03)
Secondary β-deuterium isotope effects on amine basicities are measured using a remarkably precise NMR titration method. Deuteration is found to increase the basicity of methylamine, dimethylamine, benzylamine, N,N-dimethylaniline, 2-methyl-2-azanorbornane, and pyrrolizidine. The increase in dimethylamine arises entirely from enthalpy, contrary to a previous report. The method permits a determination of intramolecular isotope effects in 1-benzyl-4-methylpiperidine and 2-benzyl-2-azanorbornane. It is found that deuteration has a larger isotope effect when either antiperiplanar or synperiplanar to a lone pair, but the synperiplanar effect is smaller, as confirmed by computations. The isotope effect is attributed to a lowered zero-point energy of a C-H bond adjacent to an amine nitrogen, arising from delocalization of either a syn or an anti lone pair, and with no detectable angle-independent inductive effect.