341363
(1R,2S,5R)-(+)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate
99%
Synonym(s):
(+)-8-Phenylmenthyl chloroacetate
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About This Item
Empirical Formula (Hill Notation):
C18H25ClO2
CAS Number:
Molecular Weight:
308.84
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352101
MDL number:
Assay:
99%
Form:
solid
InChI
1S/C18H25ClO2/c1-13-9-10-15(16(11-13)21-17(20)12-19)18(2,3)14-7-5-4-6-8-14/h4-8,13,15-16H,9-12H2,1-3H3/t13-,15-,16-/m1/s1
SMILES string
C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)CCl)C(C)(C)c2ccccc2
InChI key
GYWWQECFQIGECM-FVQBIDKESA-N
assay
99%
form
solid
optical activity
[α]25/D +22°, c = 1.2 in carbon tetrachloride
mp
82-84 °C (lit.)
functional group
chloro, ester, phenyl
Application
(1R,2S,5R)-(+)-5-Methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate may be used in the synthesis of (-)-8-phenylmenthol, (+)-8-phenylmenthyl isocyanoacetate and (+)-cularine.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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An efficient synthesis of (+)-8-phenylmenthyl isocyanoacetate.
Solladie-Cavallo A and Quazzotti S.
Tetrahedron Asymmetry, 3(1), 39-42 (1992)
A diastereoselective radical cyclisation approach to pyroglutamates.
Goodall K and Parsons AF.
Tetrahedron Letters, 38(3), 491-494 (1997)
Diastereoselective synthesis of cularine alkaloids via enium ions and an easy entry to isoquinolines by aza-Wittig electrocyclic ring closure.
Rodrigues JAR, et al.
The Journal of Organic Chemistry, 69(9), 2920-2928 (2004)
1R, 2S, 5R)-5-Methyl-2-(1-methyl-1-phenylethyl) cyclohexyl chloroacetate.
Sieder F, et al.
Acta Crystallographica Section E, Structure Reports Online, 62(6), o2291-o2292 (2006)
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