24048-44-0

Basic information

• Product Name: (1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene
• Synonyms: (1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene;(1R,4S,5S)-1,8-Dimethyl-4-(1-methylethenyl)spiro[4.5]dec-7-ene;1,8-Dimethyl-4-isopropenylspiro[4.5]dec-7-ene
• CAS NO: 24048-44-0
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• Mol File: 24048-44-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 273.1°Cat760mmHg
• Flash Point: 107.2°C
• Appearance: /
• Density: 0.89g/cm³
• Vapor Pressure: 0.00978mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: (1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene(24048-44-0)
• EPA Substance Registry System: (1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene(24048-44-0)

Safety Data

• Hazardous Substances Data: 24048-44-0(Hazardous Substances Data)

Usage

General Description

The chemical "(1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene" is a spirocyclic compound with a molecular formula C15H26. It is a bicyclic organic compound with a spiro carbon atom, and its structure is characterized by a decalin ring system. The compound contains two methyl groups, a propenyl group, and a spirodecane structure. It is commonly used in the field of organic synthesis and can be found in various natural products and pharmaceuticals. This chemical may have potential applications in the development of new drugs or as a building block in organic chemistry synthesis.

InChI:InChI=1/C15H24/c1-11(2)14-6-5-13(4)15(14)9-7-12(3)8-10-15/h7,13-14H,1,5-6,8-10H2,2-4H3/t13-,14+,15-/m1/s1

Upstream product

• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 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 
• 65408-94-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4,8-dimethylspiro<4.5>deca-6,8-diene 
• 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-β-acorenol 
• 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 
• 132557-03-0 (3aS,4S,6aR)-4-Methyl-3a-(3-oxo-butyl)-hexahydro-pentalen-1-one 
• 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 
• 28296-85-7 4-epi-α-acorenol 
• 40716-68-5 (2-cis,6-trans)-farnesyl diphosphate 

Downstream Products

• 5956-05-8 (+/-)-acorenone 
• 5956-05-8 (+/-)-acorenone B 
• 20479-49-6 Alaskan 
• 5956-05-8 4-epi-acorenone 

Relevant articles and documents

Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesvl diohosohate

We report the structures and stereochemistry of seven bisabolyl-derived sesquiterpenes arising from an unprecedented 1,6-cyclization (cisoid pathway) efficiently catalyzed by tobacco 5-epi-aristolochene synthase (TEAS). The use of (2Z,6E)-farnesyl diphosphate as an alternate substrate for recombinant TEAS resulted in a robust enzymatic cyclization to an array of products derived exclusively (≥99.5%) from the cisoid pathway, whereas these same products account for ca. 2.5% of the total hydrocarbons obtained using (2E,6E)-farnesyl diphosphate. Chromatographic fractionations of extracts from preparative incubations with the 2Z,6E substrate afforded, in addition to the acyclic allylic alcohols (2Z,6E)-farnesol (6.7%) and nerolidol (3.6%), five cyclic sesquiterpene hydrocarbons and two cyclic sesquiterpene alcohols: (+)-2-epiprezizaene (44%), (-)-α-cedrene (21.5%), (R)-(-)-β-curcumene (15.5%), R-acoradiene (3.9%), 4-epi-α-acoradiene (1.3%), and equal amounts of α-bisabolol (1.8%) and epi-R-bisalolol (1.8%). The structures, stereochemistry, and enantiopurities were established by comprehensive spectroscopic analyses, optical rotations, chemical correlations with known sesquiterpenes, comparisons with literature data, and GC analyses. The major product, (+)-2-epi-prezizaene, is structurally related to the naturally occurring tricyclic alcohol, jinkohol (2-epi-prezizaan-7 β-ol). Cisoid cyclization pathways are proposed by which all five sesquiterpene hydrocarbons are derived from a common (7R)-β-bisabolyl+/pyrophosphate - ion pair intermediate. The implications of the cisoid catalytic activity of TEAS are discussed.

Stereocontrolled Synthesis of (+/-)-Acorenone B Based on New Ring Conversion

On the basis of a new ring conversion reaction from the bicyclooctane ring to the spirodecane ring, (+/-)-acorenone B was synthesized in a stereocontrolled fashion.

Synthetic Studies on Acorane-Alaskane Sesquiterpenes. I. Total Synthesis of (+/-)-β-Acorenol

(+/-)-β-Acorenol (2) was synthesized by the methal-ammonia reduction of (1R*,3aR*,5aR*,9aR*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran (11a), which was prepared from the spirodienone