28477-64-7

Basic information

• Product Name: (1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene
• Synonyms: (1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene
• CAS NO: 28477-64-7
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• Mol File: 28477-64-7.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene(28477-64-7)
• EPA Substance Registry System: (1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene(28477-64-7)

Safety Data

• Hazardous Substances Data: 28477-64-7(Hazardous Substances Data)

Usage

General Description

The chemical compound "(1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene" is a complex, organic, and cyclic compound with a spiro[4.5]dec-7-ene structure. It contains a spiro ring system with a total of ten carbon atoms, and has two methyl groups and a 1-methylethenyl group attached to different carbon atoms in the structure. (1R,4S,5R)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene is commonly found in essential oils and is known for its pleasant aroma and potential applications in perfumery and flavoring. Its stereochemistry, with the (1R,4S,5R) configuration, indicates the specific spatial arrangement of its atoms, which can impact its properties and reactivity. Due to its complex structure and stereochemistry, this compound is of interest to researchers and chemists for better understanding its potential uses and interactions in various applications.

Upstream product

• 372-97-4 farnesyl pyrophosphate 
• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 121322-15-4 2-((1S,4R,5S)-6,7-Dibromo-4,8-dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol 
• 28296-85-7 (+/-)-4-epi-β-acorenol 
• 89949-49-5 2-((1S,4R,5R)-4,8-Dimethyl-spiro[4.5]dec-6-en-1-yl)-propan-2-ol 
• 94392-92-4 rac-(1R,4S,5R)-6-bromo-1-(1-hydroxy-1-methylethyl)-4,8-dimethylspiro<4.5>dec-7-ene 
• 43219-77-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4-methyl-8-methylenespiro<4.5>dec-6-ene 
• 28296-85-7 4-epi-α-acorenol 
• 132557-02-9 (3aR,4R,6aS)-3a-But-3-enyl-4-methyl-hexahydro-pentalen-1-one 
• 87017-52-5 6-methylbicyclo<3.3.0>oct-1(5)-en-2-one 
• 65408-94-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4,8-dimethylspiro<4.5>deca-6,8-diene 
• 28296-85-7 (+/-)-β-acorenol 
• 917-54-4 methyllithium 
• 132557-04-1 (1R,4S,5S)-4,8-Dimethyl-spiro[4.5]dec-7-ene-1-carboxylic acid 2-hydroxy-ethyl ester 

Downstream Products

• 5956-05-8 (+/-)-acorenone 
• 5956-05-8 (+/-)-acorenone B 
• 5956-05-8 4-epi-acorenone 

Relevant articles and documents

Structure of epi-isozizaene synthase from streptomyces coelicolor A3(2), a platform for new terpenoid cyclization templates

The X-ray crystal structure of recombinant epi-isozizaene synthase (EIZS), a sesquiterpene cyclase from Streptomyces coelicolor A3(2), has been determined at 1.60 A resolution. Specifically, the structure of wild-type EIZS is that of its closed conformation in complex with three Mg2+ ions, inorganic pyrophosphate (PPi), and the benzyltriethylammonium cation (BTAC). Additionally, the structure of D99N EIZS has been determined in an open, ligand-free conformation at 1.90 A resolution. Comparison of these two structures provides the first view of conformational changes required for substrate binding and catalysis in a bacterial terpenoid cyclase. Moreover, the binding interactions of BTAC may mimic those of a carbocation intermediate in catalysis. Accordingly, the aromatic rings of F95, F96, and F198 appear to be well-oriented to stabilize carbocation intermediates in the cyclization cascade through cation π interactions. Mutagenesis of aromatic residues in the enzyme active site results in the production of alternative sesquiterpene product arrays due to altered modes of stabilization of carbocation intermediates as well as altered templates for the cyclization of farnesyl diphosphate. Accordingly, the 1.64 A resolution crystal structure of F198A EIZS in a complex with three Mg2+ ions, PPi, and BTAC reveals an alternative binding orientation of BTAC; alternative binding orientations of a carbocation intermediate could lead to the formation of alternative products. Finally, the crystal structure of wild-type EIZS in a complex with four Hg 2+ ions has been determined at 1.90 A resolution, showing that metal binding triggers a significant conformational change of helix G to cap the active site.

Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. Total Synthesis of (+/-)-Acorenone

The metal-ammonia reduction of the cyclopentabenzofuran derivative (2b) afforded a mixture of 4-epi-β-acorenol (5), a disubstituted olefin (8) as the main product, and a perhydro compound (9).Compound 8 was converted to 5 via the exo-diene (15).Dehydration of 5 afforded the 4-epi-β-acoradiene (6), selective reduction of which gave the monoolefin (7), and then the allylic oxidation of 7 gave (+/-)-acorenone (3) in good yield.Keywords - acorane-alaskane sesquiterpene; acorenone; cyclopentabenzofuran; total synthesis; 4-epi-β-acorenol; 4-epi-α-acorenol; 4-epi-β-acoradiene; metal-ammonia reduction; conjugate reduction; terminal olefin reduction.

Novel Cyclopentabenzofuran Intermediates for the Synthesis of Acorane-Alaskane Sesquiterpenes: Total Synthesis of (+/-)-β-Acorenol and (+/-)-Acorenone

Cyclopentabenzofuran derivatives (5a) and (5b) were synthesized from spirodienone esters (6a) and (6b), respectively, and the utility of these intermediates in acorane-alaskane sesquiterpene synthesis is illustrated by their conversion into (+/-)-β-acorenol (4a) and (+/-)-acorenone (1).