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921459

Sigma-Aldrich

trans-(+)-limonene oxide

Synonym(s):

(1S,4R,6R)-4-Isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
6909-30-4
Molecular Weight:
152.23
MDL number:
MFCD16652609
UNSPSC Code:
12352212
NACRES:
NA.22

form

liquid

Quality Level

100

functional group

ether

SMILES string

O1[C@@]2([C@H]1C[C@@H](CC2)C(=C)C)C

InChI

1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9-,10+/m1/s1

InChI key

CCEFMUBVSUDRLG-BBBLOLIVSA-N

Application

trans-(+)-Limonene oxide is a valuable chiral terpene oxide building block. Used in the synthesis of Phosphorus Incorporation (PI) reagents, as a biologically sourced component of polycarbonate polymers, and as a building block for synthetic applications requiring a reactive epoxide or alkene.

Other Notes

Enantiodivergent Formation of C–P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides

Fe-Catalyzed C–C Bond Construction from Olefins via Radicals

related product

Product No.
Description
Pricing

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

149.0 °F - closed cup

Flash Point(C)

65 °C - closed cup

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Ke-Yin Ye et al.
Journal of the American Chemical Society, 141(24), 9548-9554 (2019-06-11)
Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely, bimetallic radical redox-relay, in the
Samantha A Green et al.
Journal of the American Chemical Society, 141(19), 7709-7714 (2019-04-30)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated
Julian C Lo et al.
Journal of the American Chemical Society, 139(6), 2484-2503 (2017-01-18)
This Article details the development of the iron-catalyzed conversion of olefins to radicals and their subsequent use in the construction of C-C bonds. Optimization of a reductive diene cyclization led to the development of an intermolecular cross-coupling of electronically-differentiated donor

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