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664073

Sigma-Aldrich

(S)-(+)-2,3,7,7a-Tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione

97%

Synonym(s):

(+)-5,6,7,8-Tetrahydro-8-methylindan-1,5-dione, (+)-7,7a-Dihydro-7α, β-methyl-1,5(6H)-indandione, (S)-(+)-Hajos-Parrish diketone, (S)-Hajos dione, (S)-Hajos ketone, (S)-Hajos-Wiechert ketone

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About This Item

Empirical Formula (Hill Notation):
C10H12O2
CAS Number:
17553-86-5
Molecular Weight:
164.20
Beilstein/REAXYS Number:
1619112
MDL number:
MFCD00012272
UNSPSC Code:
12352115
PubChem Substance ID:
24884676
NACRES:
NA.22

assay

97%

form

solid

mp

57-64 °C

SMILES string

C[C@]12CCC(=O)C=C1CCC2=O

InChI

1S/C10H12O2/c1-10-5-4-8(11)6-7(10)2-3-9(10)12/h6H,2-5H2,1H3/t10-/m0/s1

InChI key

FNYAZSZTENLTRT-JTQLQIEISA-N

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Application

(S)-(+)-Hajos-Parrish diketone can be used as a reactant in:
  • The total synthesis of steroidal alkaloids cortistatins.
  • The stereoselective preparation of hydroanthracenol and related polycyclic compounds via Ti(Oi-Pr)4-promoted photoenolization Diels-Alder reaction.
  • The synthesis of γ,γ-disubstituted allyldiboron compounds by reacting with allylic 1,1-diboronate reagents via Cu-catalyzed borylation and 1,2-addition reaction.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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Construction of key building blocks towards the synthesis of cortistatins
Indu S, et al.
Organic & Biomolecular Chemistry, 18(13), 2432-2446 (2020)
Cu-Catalyzed Diastereo-and Enantioselective Reactions of γ, γ-Disubstituted Allyldiboron Compounds with Ketones
Zanghi JM and Meek SJ
Angewandte Chemie (International ed. in English), 8(1), 1-10 (2020)
Singlet oxygen-mediated selective C--H bond hydroperoxidation of ethereal hydrocarbons
Sagadevan A, et al.
Nature Communications, 8(1), 1-8 (2017)

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