19889-99-7

Basic information

• Product Name: [1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol
• Synonyms: [1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol;(1S)-cis-Pinocarvenol;(1S,3S,5S)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptane-3-ol;(1S,5α)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3β-ol;Einecs 243-406-5
• CAS NO: 19889-99-7
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 243-406-5
• Mol File: 19889-99-7.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 217.5°Cat760mmHg
• Flash Point: 90.1°C
• Appearance: /
• Density: 1g/cm³
• CAS DataBase Reference: [1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol(19889-99-7)
• EPA Substance Registry System: [1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol(19889-99-7)

Safety Data

• Hazardous Substances Data: 19889-99-7(Hazardous Substances Data)

Usage

Description

[1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is a stereochemically defined bicyclic compound with a unique molecular structure and stereochemical arrangement. It features a bicyclo[3.1.1] structure, with methyl groups at the 6th position and a methylene group at the 2nd position. Additionally, it contains a hydroxyl group at the 3rd position, which may contribute to its potential applications in various fields.

Uses

Used in Organic Chemistry:
[1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is used as a building block for the synthesis of more complex organic molecules. Its unique structure and stereochemistry make it a valuable compound for creating novel chemical entities with potential applications in various industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is used as a starting material for the development of new drugs. Its specific molecular structure and stereochemistry may allow for the creation of innovative therapeutic agents with improved efficacy and selectivity.
Used in Material Science:
[1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol's unique molecular structure and stereochemistry also make it a potential candidate for the development of new materials with specific properties. It could be used in the creation of advanced materials for various applications, such as in electronics, coatings, or adhesives.
Used in Chemical Synthesis:
[1S-(1alpha,3beta,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol can be used as an intermediate in the synthesis of other valuable compounds. Its unique structure and stereochemistry may facilitate the development of new synthetic routes and improve the overall efficiency of chemical reactions.

Upstream product

• 80-56-8 Pinene 
• 177698-19-0 Beta-pinene 
• 58434-29-0 myrtenyl hydroperoxide 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 515-00-4 myrtenol 
• 22321-84-2 trans-pinocarveyl hydroperoxide 
• 17004-05-6 3-amino-β-pinene 
• 22321-84-2 pinocarveyl hydroperoxide 
• 1686-14-2 α-pinene epoxide 
• 18172-67-3 beta-pinene 
• 50-00-0 formaldehyd 
• 1010-46-4 (1S:2S)-2,10-dibromo-pinanone-⁽³⁾ 
• 64-19-7 acetic acid 
• 19890-00-7 (1S)-pinocarvone 

Downstream Products

• 2734-31-8 (1R,2R,3S,5S)-(+)-neoisopinocampheol 
• 473-62-1 (1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 
• 18172-67-3 (?)-β-pinene 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 39166-57-9 (1R:2R:3S)-3-Acetoxy-pinan 

Relevant articles and documents

Design of stable mixed-metal MIL-101(Cr/Fe) materials with enhanced catalytic activity for the Prins reaction

This work highlights the benefit of designing mixed-metal (Cr/Fe) MOFs for enhanced chemical stability and catalytic activity. A robust and stable mixed-metal MIL-101(Cr/Fe) was prepared through a HF-free direct hydrothermal route with Fe3+ content up to 21 wt%. The incorporation of Fe3+ cations in the crystal structure was confirmed by 57Fe M?ssbauer spectrometry. The catalytic performance of the mixed metal MIL-101(Cr/Fe) was evaluated in the Prins reaction. MIL-101(Cr/Fe) exhibited a higher catalytic activity compared to MIL-101(Cr), improved chemical stability compared to MIL-101(Fe) and a higher catalytic activity for bulky substrates compared to MIL-100(Fe). In situ infra-red spectroscopy study suggests that the incorporation of Fe3+ ions in MIL-101 structure leads to an increase in Lewis acid sites. It was thus concluded that the predominant role of Cr3+ ions was to maintain the crystal structure, while Fe3+ ions enhanced the catalytic activity.

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely, bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton transfer/electron transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.

Synthesis of bimetallic Zr(Ti)-naphthalendicarboxylate MOFs and their properties as Lewis acid catalysis

Bimetallic Zr(Ti)-NDC based metal-organic frameworks (MOFs) have been prepared by incorporation of titanium(iv) into zirconium(iv)-NDC-MOFs (UiO family). The resulting materials maintain thermal (up to 500 °C), chemical and structural stability with respect to parent Zr-MOFs as can be deduced from XRD, N2 adsorption, FTIR and thermal analysis. The materials have been studied in Lewis acid catalyzed reactions, such as, domino Meerwein-Ponndorf-Verley (MPV) reduction-etherification of p-methoxybenzaldehyde with butanol, isomerization of α-pinene oxide and cyclization of citronellal.