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334235

Sigma-Aldrich

(3S-cis)-(+)-Tetrahydro-3-isopropyl-7a-methylpyrrolo[2,1-b]oxazol-5(6H)-one

95%

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About This Item

Empirical Formula (Hill Notation):
C10H17NO2
CAS Number:
Molecular Weight:
183.25
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:

Assay

95%

form

liquid

optical activity

[α]27/D +90°, c = 2.8 in ethanol

refractive index

n20/D 1.473 (lit.)

bp

70 °C/0.4 mmHg (lit.)

density

1.027 g/mL at 25 °C (lit.)

SMILES string

CC(C)[C@H]1CO[C@]2(C)CCC(=O)N12

InChI

1S/C10H17NO2/c1-7(2)8-6-13-10(3)5-4-9(12)11(8)10/h7-8H,4-6H2,1-3H3/t8-,10-/m1/s1

InChI key

NUUDVADIQSLTCN-PSASIEDQSA-N

Application

Chiral bicyclic lactams such as this are useful templates for the asymmetric synthesis of a variety of natural and unnatural products. High levels of asymmetric induction have been obtained in cycloadditions, alkylations, conjugate additions, annulations, and dihydroxylations.

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

136.4 °F - closed cup

Flash Point(C)

58 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Fray, A.H. Meyers, A.I.
The Journal of Organic Chemistry, 61, 3362-3362 (1996)
Munchhoff, M.J. Meyers, A.I.
The Journal of Organic Chemistry, 60, 7084-7084 (1995)
Brengel, G.P. Meyers, A.I.
The Journal of Organic Chemistry, 61, 3230-3230 (1996)
Andres, C.J. et al.
Tetrahedron Letters, 60, 3189-3189 (1995)
Romo, D. Meyers, A.I.
Tetrahedron, 47, 9503-9503 (1991)

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