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

• 40716-68-5 (2-cis,6-trans)-farnesyl diphosphate 
• 28296-85-7 4-epi-α-acorenol 
• 28296-85-7 (+/-)-4-epi-β-acorenol 
• 121322-15-4 2-((1S,4R,5S)-6,7-Dibromo-4,8-dimethyl-spiro[4.5]dec-1-yl)-propan-2-ol 
• 43219-77-8 rac-(1R,4S,5R)-1-(1-hydroxy-1-methylethyl)-4-methyl-8-methylenespiro<4.5>dec-6-ene 
• 94392-92-4 rac-(1R,4S,5R)-6-bromo-1-(1-hydroxy-1-methylethyl)-4,8-dimethylspiro<4.5>dec-7-ene 
• 89949-49-5 2-((1S,4R,5R)-4,8-Dimethyl-spiro[4.5]dec-6-en-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 
• 87017-52-5 6-methylbicyclo<3.3.0>oct-1(5)-en-2-one 
• 132557-02-9 (3aR,4R,6aS)-3a-But-3-enyl-4-methyl-hexahydro-pentalen-1-one 
• 132557-03-0 (3aS,4S,6aR)-4-Methyl-3a-(3-oxo-butyl)-hexahydro-pentalen-1-one 
• 132557-04-1 (1R,4S,5S)-4,8-Dimethyl-spiro[4.5]dec-7-ene-1-carboxylic acid 2-hydroxy-ethyl ester 
• 917-54-4 methyllithium 
• 28296-85-7 (+/-)-β-acorenol 

Downstream Products

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

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.

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