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

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

Uses

Used in Organic Synthesis:
(1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene is used as a building block in organic synthesis for its unique spirocyclic structure and functional groups, enabling the creation of various complex organic molecules.
Used in Pharmaceutical Development:
(1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene is used as a potential candidate in the development of new drugs due to its presence in natural products and pharmaceuticals, suggesting potential biological activity and therapeutic applications.
Used in Natural Product Isolation:
(1R,4S,5S)-1,8-dimethyl-4-prop-1-en-2-yl-spiro[4.5]dec-8-ene is used in the isolation and identification of natural products, as its unique structure can help in the characterization and understanding of bioactive compounds found in nature.

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

• 40716-68-5 (2-cis,6-trans)-farnesyl diphosphate 
• 28296-85-7 4-epi-α-acorenol 
• 28296-85-7 (+/-)-4-epi-β-acorenol 
• 917-54-4 methyllithium 
• 28296-85-7 (+/-)-β-acorenol 
• 121322-15-4 2-((1S,4R,5S)-6,7-Dibromo-4,8-dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol 
• 74320-28-8 (1R^*,3aS^*,5aS^*,9aS^*)-2,3,3a,4-tetrahydro-1,4,4,7-tetramethyl-1H,5aH-cyclopentabenzofuran 
• 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 
• 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 

Downstream Products

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

Relevant articles and documents

Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates

Sesquiterpene skeletal complexity in nature originates from the enzyme-catalyzed ionization of (trans,trans)-farnesyl diphosphate (FPP) (1a) and subsequent cyclization along either 2,3-transoid or 2,3-cisoid farnesyl cation pathways. Tobacco 5-epi-aristolochene synthase (TEAS), a transoid synthase, produces cisoid products as a component of its minor product spectrum. To investigate the cryptic cisoid cyclization pathway in TEAS, we employed (cis,trans)-FPP (1b) as an alternative substrate. Strikingly, TEAS was catalytically robust in the enzymatic conversion of (cis,trans)-FPP (1b) to exclusively (?99.5%) cisoid products. Further, crystallographic characterization of wild-type TEAS and a catalytically promiscuous mutant (M4 TEAS) with 2-fluoro analogues of both all-trans FPP (1a) and (cis,trans)-FPP (1b) revealed binding modes consistent with preorganization of the farnesyl chain. These results provide a structural glimpse into both cisoid and transoid cyclization pathways efficiently templated by a single enzyme active site, consistent with the recently elucidated stereochemistry of the cisoid products. Further, computational studies using density functional theory calculations reveal concerted, highly asynchronous cyclization pathways leading to the major cisoid cyclization products. The implications of these discoveries for expanded sesquiterpene diversity in nature are discussed.

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. 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.

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

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).