6813-05-4

Basic information

• Product Name: [1R,3aβ,7aβ,(-)]-Octahydro-4-methyl-8-methylene-7α-isopropyl-1α,4α-methano-1H-indene
• Synonyms: [1R,3aβ,7aβ,(-)]-Octahydro-4-methyl-8-methylene-7α-isopropyl-1α,4α-methano-1H-indene
• CAS NO: 6813-05-4
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 370.7897
• Mol File: 6813-05-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 502.2°C at 760 mmHg
• Flash Point: 257.5°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 3.26E-10mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: [1R,3aβ,7aβ,(-)]-Octahydro-4-methyl-8-methylene-7α-isopropyl-1α,4α-methano-1H-indene(CAS DataBase Reference)
• NIST Chemistry Reference: [1R,3aβ,7aβ,(-)]-Octahydro-4-methyl-8-methylene-7α-isopropyl-1α,4α-methano-1H-indene(6813-05-4)
• EPA Substance Registry System: [1R,3aβ,7aβ,(-)]-Octahydro-4-methyl-8-methylene-7α-isopropyl-1α,4α-methano-1H-indene(6813-05-4)

Safety Data

• Hazardous Substances Data: 6813-05-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H15ClN4O3/c1-11-3-5-13(6-4-11)22-18(24)15(12(2)21-22)10-20-17-9-14(23(25)26)7-8-16(17)19/h3-10,20-21H,2H2,1H3

Upstream product

• 106-28-5 Farnesol 
• 3047-64-1 ((1S,3aR,4S,7S)-7-Isopropyl-4-methyl-octahydro-1,4-methano-inden-8-yl)-methanol 
• 3047-64-1 (1RS, 2SR, 3SR, 6SR, 7RS, 8SR)(-3-isopropyl-6-methyltricyclo<4.4.0.0^2,8>dec-7-yl)methanol 
• 159949-84-5 7-Isopropylidene-4-methyl-8-methylene-octahydro-1,4-methano-indene 
• 6018-41-3 methyl coumalate 
• 4430-91-5 2,3-dimethyl-cyclohexa-1,3-diene 
• 159949-83-4 7-Isopropylidene-4-methyl-8-methylene-2,3,3a,4,7,7a-hexahydro-1H-1,4-methano-indene 
• 159949-81-2 C₁₅H₂₂O 
• 159949-80-1 C₁₄H₁₈O₂ 
• 870-63-3 prenyl bromide 
• 41531-62-8 8-iodocamphor ethylene acetal 
• 21966-94-9 (1S,3aS,5R)-5-Isopropyl-1,7a-dimethyl-octahydro-1,4-methano-inden-8-one 
• 22338-91-6 (+/-)-3-isopropyl-6-methyltricyclo<4.4.0.0^2,8>decan-7-one 

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.