16641-59-1

Basic information

• Product Name: (1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene
• Synonyms: Copacamphene
• CAS NO: 16641-59-1
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35106
• Mol File: 16641-59-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene(16641-59-1)
• EPA Substance Registry System: (1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene(16641-59-1)

Safety Data

• Hazardous Substances Data: 16641-59-1(Hazardous Substances Data)

Usage

Description

(1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene is a bicyclic terpene belonging to the isoprenoid family. It is a colorless, volatile liquid with a strong odor and is commonly found in plants, contributing to the characteristic scents of herbs and spices such as basil and oregano.

Uses

Used in Perfumery and Flavoring Industry:
(1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene is used as a fragrance ingredient and flavoring agent due to its strong odor and natural occurrence in various herbs and spices.
Used in Organic Synthesis:
(1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene is utilized as a building block in the synthesis of other organic compounds, contributing to the development of new chemical products and materials.
Used in Medicinal Research:
(1R,3aβ,7aβ)-Octahydro-4-methyl-8-methylene-7-isopropyl-1α,4α-methano-1H-indene is studied for its potential medicinal properties, such as anti-inflammatory and antioxidant effects, which may lead to the development of new therapeutic agents.

Upstream product

• 21966-94-9 (1S,3aS,5R)-5-Isopropyl-1,7a-dimethyl-octahydro-1,4-methano-inden-8-one 
• 917-54-4 methyllithium 
• 22338-91-6 (+/-)-3-isopropyl-6-methyltricyclo<4.4.0.0^2,8>decan-7-one 
• 21966-93-8 (+/-)-Isoylangoborneol 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 77407-17-1 methyl (1RS,2RS,3RS,6SR,7RS)-1-methyl-8-oxotricyclo<4.3.O.O^3,7>nonane-2-carboxylate 
• 77407-17-1 methyl (1RS, 2RS, 3RS, 6RS, 7RS)-1-methyl-8-oxotricyclo<4.3.O.O^3,7>nonane-2-carboxylate 
• 78012-08-5 (1RS, 2RS, 3SR, 6SR, 7RS)-2-(tert-butyldimethylsilyoxy)methyl-5-(trimethylsilyloxy)tricyclo<4.3.0.0^3,7>non-4-ene 
• 108794-28-1 (1S,3aR,4R,7R)-4-Methyl-6-trimethylsilanyloxy-1,2,3,3a,4,6a-hexahydro-1,4-methano-pentalene-7-carboxylic acid methyl ester 
• 78012-06-3 (1RS, 2SR, 6SR, 7RS, 8RS)-7-(tert-butyldimethylsilyloxy)methyl-6-methyltricyclo<4.4.0.0^2,8>dec-4-en-3-one 
• 108794-35-0 (1RS, 2SR, 6SR, 7RS, 8SR )-7-(tert-butyldimethylsilyloxy)methyl-3-isopropylidene-6-methyltricyclo<4.4.0.0^2,8>decane 
• 78012-07-4 (1RS, 2SR, 6SR, 7RS, 8RS)-7-(tert-butyldimethylsilyloxy)methyl-6-methyltricyclo<4.4.0.0^2,8>decan-3-one 
• 108794-33-8 (1RS, 2RS, 4RS, 5RS, 6SR, 9SR, 10SR)-10-(tert-butyldimethylsilyloxy)methyl-4-(trimethylsilyloxy)tetracyclo<4.4.0.0^2,4.0^5,9>decane 
• 108794-36-1 (1RS, 2SR, 3SR, 6SR, 7RS, 8SR )-7-(tert-butyldimethylsilyloxy)methyl-3-isopropyl-6-methyltricyclo<4.4.0.0^2,8>decane 

Relevant articles and documents

Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers

Sesquiterpene synthases catalyze with different catalytic fidelity the cyclization of farnesyl pyrophosphate (FPP) into hundreds of known compounds with diverse structures and stereochemistries. Two sesquiterpene synthases, Cop4 and Cop6, were previously isolated from Coprinus cinereus as part of a fungal genome survey. This study investigates the reaction mechanism and catalytic fidelity of the two enzymes. Cyclization of all-trans-FPP ((E,E)-FPP) was compared to the cyclization of the cis-trans isomer of FPP ((Z,E)-FPP) as a surrogate for the secondary cisoid neryl cation intermediate generated by sesquiterpene synthases, which are capable of isomerizing the C2-C3 π bond of all-trans-FPP. Cop6 is a "high-fidelity" α-cuprenene synthase that retains its fidelity under various conditions tested. Cop4 is a catalytically promiscuous enzyme that cyclizes (E,E)-FPP into multiple products, including (-)-germacrene D and cubebol. Changing the pH of the reaction drastically alters the fidelity of Cop4 and makes it a highly selective enzyme. Cyclization of (Z,E)-FPP by Cop4 and Cop6 yields products that are very different from those obtained with (E,E)-FPP. Conversion of (E,E)-FPP proceeds via a (6R)-β-bisabolyl carbocation in the case of Cop6 and an (E,E)-germacradienyl carbocation in the case of Cop4. However, (Z,E)-FPP is cyclized via a (6S)-β-bisabolene carbocation by both enzymes. Structural modeling suggests that differences in the active site and the loop that covers the active site of the two enzymes might explain their different catalytic fidelities.

THE INTRAMOLECULAR DIELS-ALDER REACTIONS OF (E)- AND (Z)-METHYL 5--2-PENTENOATE. A STEROSELECTIVE SYNTHESIS OF (+/-)-SATIVENE

The intramolecular Diels-Alder reactions of (E)- and (Z)-trimethylsilyl cyclopentadienyl ethers, (E)-6a and (Z)-6a, proceed with excellent stereo- and regioselectivity.Starting from the tricyclic keto ester 8, available from the former reaction, a stereoselective synthesis of (+/-)-sativene (26) is described.

A STEREOSELECTIVE TOTAL SYNTHESYS OF (+/-)-SATIVENE

(+/-)-Sativene (3) is stereoselectively synthesised from tricyclic ketoester 1 in 32percent overall yield.