Himbeline - CAS 518-99-0

Catalog:	BB064153
Product Name:	Himbeline
CAS:	518-99-0
Synonyms:	Himbeline (6CI); [3S-[3a,3aa,4b[1E,2(2S,6R)],4ab,8aa,9aa]]-decahydro-3-methyl-4-[2-(6-methyl-2-piperidinyl)ethenyl]naphtho[2,3-c]furan-1(3H)-one; (3S,3aR,4R,4aS,8aR,9aS)-Decahydro-3-methyl-4-[(1E)-2-[(2R,6S)-6-methyl-2-piperidinyl]ethenyl]naphtho[2,3-c]furan-1(3H)-one; (+)-Himbeline; Himbelin; N-Demethylhimbacine

Technical Data

IUPAC Name:	(3S,3aR,4R,4aS,8aR,9aS)-3-methyl-4-[(E)-2-[(2S,6R)-6-methylpiperidin-2-yl]ethenyl]-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-1-one
Description:	Himbeline is used in the enantioselective total synthesis of (+)-himbacine and (+)-himbeline from (S)-2-methylpiperidine L-tartrate.
Molecular Weight:	331.49
Molecular Formula:	C21H33NO2
Canonical SMILES:	CC1CCCC(N1)C=CC2C3CCCCC3CC4C2C(OC4=O)C
InChI:	InChI=1S/C21H33NO2/c1-13-6-5-8-16(22-13)10-11-18-17-9-4-3-7-15(17)12-19-20(18)14(2)24-21(19)23/h10-11,13-20,22H,3-9,12H2,1-2H3/b11-10+/t13-,14+,15-,16+,17+,18-,19+,20-/m1/s1
InChI Key:	GEQKTSPOTKEYOG-RQEHFGSBSA-N
References:	Chackalamannil, S.; et al. JACS, 118, 9812 (1996).

Complexity:	502
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	8
Defined Bond Stereocenter Count:	1
Exact Mass:	331.251129295
Formal Charge:	0
Heavy Atom Count:	24
Hydrogen Bond Acceptor Count:	3
Hydrogen Bond Donor Count:	1
Isotope Atom Count:	0
Monoisotopic Mass:	331.251129295
Rotatable Bond Count:	2
Topological Polar Surface Area:	38.3Å²
Undefined Atom Stereocenter Count:	0
Undefined Bond Stereocenter Count:	0
XLogP3:	4.6