466-61-5 Usage
Description
Lycopodine is an alkaloid that has been discovered in all Lycopodium species except for L. saururus Lam. It was first obtained by B6deker, who assigned it the formula C32Hs203N2, which was later altered and confirmed by Achmatowicz, Uzieblo, Manske, and Marion. Lycopodine forms colorless prisms from Et20 and has a specific optical rotation of [α]20D 9.01° (Me2CO). It can yield crystalline salts and derivatives, such as the perchlorate, methochloride, methiodide, and a hydrazone. Lycopodine is resistant to hydrogenation even under high pressure and temperature conditions, and it undergoes selenium dehydrogenation to form a complex mixture of bases.
Uses
1. Used in Pharmaceutical Industry:
Lycopodine is used as a pharmaceutical compound for its potential therapeutic applications. The expression is: Lycopodine is used as a pharmaceutical compound for its potential therapeutic applications.
2. Used in Chemical Synthesis:
Lycopodine is used as a starting material for the synthesis of various derivatives and salts, which can be further explored for their chemical and biological properties. The expression is: Lycopodine is used as a starting material for chemical synthesis for exploring its chemical and biological properties.
3. Used in Research and Development:
Lycopodine is used as a subject of study in research and development, particularly in the fields of organic chemistry, natural products chemistry, and pharmacology. The expression is: Lycopodine is used as a subject of study in research and development for advancing knowledge in organic chemistry, natural products chemistry, and pharmacology.
4. Used in Analytical Chemistry:
Lycopodine can be used as a reference compound in analytical chemistry for the development and validation of analytical methods, as well as for the identification and quantification of related compounds in complex mixtures. The expression is: Lycopodine is used as a reference compound in analytical chemistry for method development, validation, and compound identification.
Please note that the provided materials do not explicitly mention specific applications of Lycopodine. The uses listed above are inferred based on the general properties and characteristics of the compound.
References
Bodeker., Annalen., 208,363 (1881)
Achmatowicz, Uzieblo., Rocz. Chern., 18,89 (1938)
Manske, Marion., Can. 1. Res., 20B, 87 (1942)
Marion, Manske., ibid, 20B, 153 (1942)
Manske, Marion., 1. Arner. Chern. Soc., 69,2126 (1947)
Anet., Tetrahedron Lett., 20, 13 (1960)
Harrison et al., Can. 1. Chern., 39,2086 (1961)
Check Digit Verification of cas no
The CAS Registry Mumber 466-61-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 6 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 466-61:
(5*4)+(4*6)+(3*6)+(2*6)+(1*1)=75
75 % 10 = 5
So 466-61-5 is a valid CAS Registry Number.
InChI:InChI=1/C16H25NO/c1-11-8-12-9-15(18)14-5-3-7-17-6-2-4-13(12)16(14,17)10-11/h11-14H,2-10H2,1H3/t11-,12+,13-,14-,16-/m1/s1
466-61-5Relevant articles and documents
Concise asymmetric total synthesis of lycopodine and flabelliformine via cascade cyclization reaction
Wada, Kentaro,Kogure, Noriyuki,Kitajima, Mariko,Takayama, Hiromitsu
, p. 187 - 190 (2018/12/11)
The shortest asymmetric total synthesis of lycopodine (3) and the first asymmetric total synthesis of flabelliformine (4) were accomplished by a strategy that features a cascade cyclization of linear substrate (5) to construct tetracyclic structure (6).
Development of an enantioselective route toward the lycopodium alkaloids: Total synthesis of lycopodine
Yang, Hua,Carter, Rich G.
supporting information; experimental part, p. 4929 - 4938 (2010/10/21)
(Figure presented) Synthesis of a C15-desmethyl tricycle core of lycopodine has been accomplished. Key steps in the synthetic sequence include organocatalytic, intramolecular Michael addition of a keto sulfone and a tandem 1,3-sulfonyl shift/Mannich cyclization to construct the tricyclic core ring system. Synthetic work toward this natural product family led to the development of N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide, an organocatalyst which facilitiates enantioselective, intramolecular Michael additions. A detailed mechanistic discussion is provided for both the intramolecular Michael addition and the sulfone rearrangement. Finally, the application of these discoveries to the enantioselective total synthesis of alkaloid lycopodine is described.
THE TOTAL SYNTHESIS OF LYCOPODINE USING BRIDGEHEAD INTERMEDIATES
Kraus, George A.,Hon, Yung-Son
, p. 377 - 386 (2007/10/02)
The total synthesis of lycopodine has been achieved by two different routes.In one route a bridgehead carbocation is trapped by 3-benzyloxy-1-propanamine.In the second route a bridgehead enone is generated in situ and reacted with 3-hydroxy-1-propanamine.
