(1R,4S,4aR,9aS)-rel-4a-Methyl-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione

Name: (1R,4S,4aR,9aS)-rel-4a-Methyl-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione
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CAS No. 97804-50-7
Cat. No. CS-0158228
Purity≥98%
MDL No.MFCD29044886

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(1R,4S,4aR,9aS)-rel-4a-Methyl-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione|CS-0158228

Structure of 97804-50-7

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Description

This tetrahydroanthracenedione features a rigid, polycyclic framework with defined stereochemistry at the 1R,4S,4aR,9aS centers, enabling predictable conformational behavior. The methyl group at C4a enhances steric differentiation, while the fused quinone system offers redox activity and electron-deficient character suitable for Diels-Alder reactions and materials applications.

Application

(1R,4S,4aR,9aS)-rel-4a-Methyl-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione serves as a stable, bench-ready polycyclic dienophile in Diels–Alder reactions. Its rigid bicyclic framework provides predictable stereochemistry and excellent functional group tolerance, enabling efficient construction of complex carbocyclic and heterocyclic scaffolds. The molecule functions effectively in standard thermal cycloadditions and supports downstream derivatization for synthetic intermediates in natural product and medicinal chemistry applications.

General Information

CAS No. 97804-50-7
Cat. No. CS-0158228
Purity ≥98%
MDL No. MFCD29044886
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₁₄O₂
Molecular Weight 238.28
Synonym(s) 1,4,4a,9a-tetrahydro-4a-methyl-(1α,4α,4aα,9aα)-1,4-methaneanthracene-9,10-dione
SMILES C[C@]12[C@@H]3C=C[C@@H](C3)[C@@H]2C(=O)C4=CC=CC=C4C1=O

Computational Chemistry Data

TPSA 34.14
LogP 2.894
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

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(1R,4S,4aR,9aS)-rel-4a-Methyl-1,4,4a,9a-tetrahydro-1,4-methanoanthracene-9,10-dione

CAS No. 97804-50-7

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