10208-55-6

Basic information

• Product Name: (1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one
• Synonyms: (1R)-4a,5,6,7,8,8aβ-Hexahydro-7β-ethynyl-1β,4aβ-dimethylnaphthalen-2(1H)-one;(1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one;Isochamaecynone;Isochamecynone
• CAS NO: 10208-55-6
• Molecular Formula: C14H18O
• Molecular Weight: 202.29212
• Mol File: 10208-55-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one(10208-55-6)
• EPA Substance Registry System: (1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one(10208-55-6)

Safety Data

• Hazardous Substances Data: 10208-55-6(Hazardous Substances Data)

Usage

General Description

(1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one is a chemical compound with a complex molecular structure. It is a derivative of naphthalene and contains an ethynyl group, as well as two methyl substituents. (1R,8aβ)-7β-Ethynyl-4a,5,6,7,8,8a-hexahydro-1,4aβ-dimethylnaphthalen-2(1H)-one is a ketone, meaning it contains a carbonyl group within its molecular structure. The stereochemistry of the compound is designated as (1R,8aβ), indicating the absolute configuration of its chiral centers. Overall, this chemical compound is a highly specific and unique organic molecule with potential applications in medicinal chemistry, organic synthesis, and other scientific fields.

Upstream product

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• 75520-62-6 4αH,5β-13-noreudesm-11-yn-3α-ol 
• 75520-60-4 4αH,5β-13-noreudesm-11-en-3α-ol 
• 17974-85-5 (11S)-3-oxo-4αH,5β-eudesman-13-oic acid 
• 17974-84-4 (11S)-3-oxo-eudesma-1,4-dien-13-oic acid 

Downstream Products

• 10208-54-5 chamaecynone 

Relevant articles and documents

Synthetic approach to exo-endo cross-conjugated cyclohexadienones and its application to the syntheses of dehydrobrachylaenolide, isodehydrochamaecynone, and trans-isodehydrochamaecynone

Methodology for synthesis of exo-endo cross-conjugated dienones with trans- and cis-decalin systems has been reported. Bromination of the silyl enol ether of α′-methyl α,β-unsaturated ketones with PTAB and successive dehydrobromination of the resulting α′-bromo-α′-methyl α,β-unsaturated ketones under three conditions (DBU/PhH; TBAF/THF; Li2CO3, LiBr/DMF) gave the desired exo-endo cross-conjugated dienones in good yield. This method was applied to the syntheses of dehydrobrachylaenolide (1), isodehydro-chamaecynone (5c), and trans-isodehydrochamaecynone (11) starting from tuberiferine (7), chamaecynone (5a), and trans-chamaecynone (9). Eudesmanolides possessing an α-methylene γ-lactone moiety, i.e., 1, 7, and 13, exhibited significant inhibitory activity toward the induction of the intercellular adhesion molecule-1 (ICAM-1). Compound 1 showed greater activity than 7 and 13. All compounds possessing an ethynyl group, 5d, 9, 11, and 14, showed the same degree of termiticidal activity, and the exo-endo cross-conjugated dienone structure in 11 had no influence on the activity.

The total syntheses of chamaecynone, isochamaecynone, and dihydroisochamaecynone

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Total synthesis of dl chamaecynone, a termiticidal norsesquiterpene

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