Benzoylthiomethylecgonine

Benzoylthiomethylecgonine is a cocaine analog which includes a sulfur in replacement of an oxygen on the single bonded benzoyl ester, resulting in lower electronegativity than the parent compound.[1]

Benzoylthiomethylecgonine
Names
Preferred IUPAC name
Methyl (1R,2S,3S,5S)-3-(Benzoylsulfanyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C17H21NO3S/c1-18-12-8-9-13(18)15(16(19)21-2)14(10-12)22-17(20)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
    Key: PKDHUFYOPRGLEU-LJISPDSOSA-N
  • InChI=1/C17H21NO3S/c1-18-12-8-9-13(18)15(16(19)21-2)14(10-12)22-17(20)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
    Key: PKDHUFYOPRGLEU-LJISPDSOBR
SMILES
  • CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)SC(=O)c3ccccc3)C(=O)OC
Properties
Chemical formula
 C17H21NO3S
Molar mass 319.42 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Isomura, Shigeki; Hoffman, Timothy Z.; Wirsching, Peter; Janda, Kim D. (2002). "Synthesis, Properties, and Reactivity of Cocaine Benzoylthio Ester Possessing the Cocaine Absolute Configuration". Journal of the American Chemical Society. 124 (14): 3661–8. doi:10.1021/ja012376y. PMID 11929256.


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