518-99-0 Usage
Description
(3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one is a complex organic compound with a unique molecular structure. It is characterized by its decahydronaphtho[2,3-c]furan-1-one core, which is further modified by various substituents, including a methyl group, a vinyl group, and a piperidinyl group. (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one is likely to have specific applications in various fields due to its unique structure and properties.
Uses
1. Enantioselective Synthesis:
(3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one is used as a key intermediate in the enantioselective total synthesis of various chiral compounds, such as (+)-himbacine and (+)-himbeline, which are derived from (S)-2-methylpiperidine L-tartrate. (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one's unique stereochemistry allows for the selective synthesis of these target molecules with high enantiomeric purity.
2. Pharmaceutical Applications:
Given its complex structure and the presence of various functional groups, (3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one may have potential applications in the pharmaceutical industry. It could be used as a starting material for the development of new drugs targeting specific receptors or enzymes, or as a chiral ligand in asymmetric catalysis for the synthesis of biologically active compounds.
3. Chemical Research:
(3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one's unique structure and properties make it an interesting subject for chemical research. It could be used as a model system to study various aspects of organic chemistry, such as reaction mechanisms, stereoselectivity, and conformational analysis. Additionally, it may serve as a reference compound for the development of new analytical methods or the calibration of existing techniques.
4. Material Science:
(3S)-3β-Methyl-4α-[(E)-2-[(2S)-6β-methyl-2α-piperidinyl]vinyl]-1,3,3aβ,4,4aα,5,6,7,8,8aβ,9,9aβ-dodecahydronaphtho[2,3-c]furan-1-one's structural features, including its decahydronaphtho[2,3-c]furan-1-one core and various substituents, could potentially endow it with unique physical or chemical properties. This makes it a candidate for applications in material science, where it could be used to develop new materials with specific properties, such as optical, electronic, or mechanical characteristics.
Check Digit Verification of cas no
The CAS Registry Mumber 518-99-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 8 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 518-99:
(5*5)+(4*1)+(3*8)+(2*9)+(1*9)=80
80 % 10 = 0
So 518-99-0 is a valid CAS Registry Number.
518-99-0Relevant articles and documents
Synthesis and affinity studies of himbacine derived muscarinic receptor antagonists.
Gao, Ling-Jie,Waelbroeck, Magali,Hofman, Sven,Van Haver, Dirk,Milanesio, Marco,Viterbo, Davide,De Clercq, Pierre J
, p. 1909 - 1912 (2002)
A series of himbacine (1)-related analogues has been prepared featuring three different isomeric configurations with respect to the B-ring (a, b and natural c) and three different interconnecting two-carbon unsaturated units [natural (E)-ene, (Z)-ene, and yne]. The study of the binding affinities of the nine resulting compounds, including synthetic (+)-himbacine (3c), towards the M(1)-M(4) muscarine receptor subtypes revealed that analogues 3a and 5c display a promising 10-fold selectivity for the M(2) receptor as compared to the M(1) receptor.
Biomimetic total synthesis of (+)-himbacine
Tchabanenko, Kirill,Adlington, Robert M.,Cowley, Andrew R.,Baldwin, Jack E.
, p. 585 - 588 (2007/10/03)
(Chemical Equation Presented) On treatment with trifluoroacetic acid butenolide 14 undergoes N-Boc deprotection and condensation followed by an iminium ion activated intramolecular Diels-Alder cycloaddition to give the (+)-himbacine precursor 11 on reduct
Total synthesis of (+)-himbacine and (+)-himbeline
Chackalamannil, Samuel,Davies, Robert J.,Wang, Yuguang,Asberom, Theodros,Doller, Dario,Wong, Jesse,Leone, Daria,McPhail, Andrew T.
, p. 1932 - 1940 (2007/10/03)
Himbacine (1), a complex piperidine alkaloid isolated from the bark of Australian magnolias, is a promising lead in Alzheimer's disease research due to its potent muscarinic receptor antagonist property. We have described here a highly efficient synthetic strategy that resulted in the total synthesis of himbacine (1) in about 10% overall yield and isohimbacine (1a), an unnatural isomer of himbacine, in 18% overall yield. The total synthesis of himbacine was initially approached using an intramolecular Diels-Alder reaction as the key step to generate intermediate 5 followed by a [3 + 2] cycloaddition with nitrone 4 to produce the isoxazolidine derivative 3. Methylation followed by catalytic reduction of 3 gave 12'-hydroxyhimbacine (20), which, upon dehydration, gave isohimbacine (1a) as the sole product. In an alternative approach, an all-encompassing intramolecular Diels-Alder reaction of an appropriately substituted tetraene derivative 31, which bears the entire latent carbon framework and functional group substitution of himbacine, gave the desired advanced tricyclic intermediate 33, which was readily converted to (+)-himbeline (2) and (+)-himbacine (1).
