5989-33-3

Basic information

• Product Name: cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol
• Synonyms: cis-Linalool oxide;Linalool oxide B;Linalool oxide I;rel-1-[[(2R*,5S*)-5-Methyl-5-vinyltetrahydrofuran]-2-yl]-1-methylethanol;Z-Furanoid linalool oxide;cis-2-(Tetrahydro-5-methyl-5-vinylfuran-2-yl)-propan-2-ol;cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol;(Z)-linalooloxide,(Z)-2-methyl-2-vinyl-5-(2-hydroxy-2-proply)tetrahydrfuran,cis-linaloolfuranoxide
• CAS NO: 5989-33-3
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.24872
• EINECS: 227-814-0
• Mol File: 5989-33-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 188 °C
• Appearance: /
• Density: 1.023±0.06 g/cm3(Predicted)
• PKA: 14.57±0.29(Predicted)
• CAS DataBase Reference: cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol(5989-33-3)
• EPA Substance Registry System: cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol(5989-33-3)

Safety Data

• Hazardous Substances Data: 5989-33-3(Hazardous Substances Data)

Usage

Description

cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol is a complex chemical compound derived from tetrahydrofuran, featuring trimethyl and vinyl groups along with an alcohol functional group. This molecular structure suggests potential applications in polymer chemistry and as a building block for synthesizing other organic compounds, with its solubility and reactivity properties being of interest in various chemical processes.
Used in Chemical Synthesis Industry:
cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol is used as a building block for synthesizing other organic compounds due to its complex molecular structure and the presence of trimethyl, vinyl, and alcohol groups, which can contribute to the formation of new chemical entities.
Used in Polymer Chemistry:
As a derivative of tetrahydrofuran, cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol is used in polymer chemistry for its potential to form or modify polymers, taking advantage of its unique structural features and reactive groups.
Used in Solvent Applications:
Given its solubility properties, cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol can be used as a solvent in various chemical reactions, facilitating processes that require specific interactions with its molecular structure.
Further research would be necessary to fully explore the potential uses and properties of cis-alpha,alpha,5-trimethyl-5-vinyltetrahydrofuran-2-methanol, as its complex nature may offer additional applications in different industries.

Upstream product

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• 128344-89-8 anti-N-<1-(5-ethenyltetrahydro-5-methylfuran-2-yl)-1-methylethoxy>-2,2,6,6-tetramethylpiperidine 

Relevant articles and documents

One-pot synthesis at room temperature of epoxides and linalool derivative pyrans in monolacunary Na7PW11O39-catalyzed oxidation reactions by hydrogen peroxide

In this work, we describe a new one-pot synthesis route of valuable linalool oxidation derivatives (i.e., 2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (1a)), 2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (1b) and diepoxide (1c), using a green oxidant (i.e., hydrogen peroxide) under mild conditions (i.e., room temperature). Lacunar Keggin heteropolyacid salts were the catalysts investigated in this reaction. Among them, Na7PW11O39 was the most active and selective toward oxidation products. All the catalysts were characterized by FT-IR, TG/DSC, BET, XRD analyses and potentiometric titration. The main reaction parameters were assessed. Special attention was dedicated to correlating the composition and properties of the catalysts and their activity.

Fungal biotransformation of (±)-linalool

The biotransformation of (±)-linalool was investigated by screening 19 fungi. Product accumulation was enhanced by substrate feeding and, for the first time, lilac aldehydes and lilac alcohols were identified as fungal biotransformation byproduct using SPME-GC-MS headspace analysis. Aspergillus niger DSM 821, Botrytis cinerea 5901/02, and B. cinerea 02/FBII/2.1 produced different isomers of lilac aldehyde and lilac alcohol from linalool via 8-hydroxylinalool as postulated intermediate. Linalool oxides and 8-hydroxylinalool were the major products of fungal (±)-linalool biotransformations. Furanoid trans-(2R,5R)- and cis-(2S,5R)-linalool oxide as well as pyranoid trans-(2R,5S)- and cis-(2S, 5S)-linalool oxide were identified as the main stereoisomers with (3S,6S)-6,7-epoxylinalool and (3R,6S)-6,7-epoxylinalool as postulated key intermediates of fungal (±)-linalool oxyfunctionalization, respectively. With a conversion yield close to 100% and a productivity of 120 mg/L·day linalool oxides, Corynespora cassiicola DSM 62485 was identified as a novel highly stereoselective linalool transforming biocatalyst showing the highest productivity reported so far.

Diastereoselective titanocene-catalyzed oxidative cyclization of bishomoallylic alcohols

Bishomoallylic alcohols are converted in good yields and diastereoselectivity into tetrahydrofuranols and tetrahydropyranols by Cp2TiCl2/t-butyl hydroperoxide/activated 4? molecular sieves system.