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341363

Sigma-Aldrich

(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:
71804-27-8
Molecular Weight:
308.84
MDL number:
MFCD00040610
UNSPSC Code:
12352101
PubChem Substance ID:
24860934
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]25/D +22°, c = 1.2 in carbon tetrachloride

mp

82-84 °C (lit.)

SMILES string

C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)CCl)C(C)(C)c2ccccc2

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

InChI key

GYWWQECFQIGECM-FVQBIDKESA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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