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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:
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

Signal Word

Danger

Hazard Statements

H301,H315,H317,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

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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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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