3917-59-7

Basic information

• Product Name: [1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol
• Synonyms: [1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol;(1R,1β,5β)-Pina-2(10)-ene-3β-ol;(1R,3S,5R)-6,6-Dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol;(1β,5β)-2-Methylene-6,6-dimethylbicyclo[3.1.1]heptane-3β-ol;Einecs 223-483-1
• CAS NO: 3917-59-7
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 223-483-1
• Mol File: 3917-59-7.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 217.5°Cat760mmHg
• Flash Point: 90.1°C
• Appearance: /
• Density: 1g/cm³
• CAS DataBase Reference: [1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: [1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol(3917-59-7)
• EPA Substance Registry System: [1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol(3917-59-7)

Safety Data

• Hazardous Substances Data: 3917-59-7(Hazardous Substances Data)

Usage

Description

[1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is a bicyclic alcohol with a complex chemical structure, featuring two methyl groups and a methylene group. It belongs to the class of bicyclo compounds, characterized by a unique ring structure with two fused cyclohexane rings. [1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is represented in its R-configuration, indicating that the highest priority groups are arranged in a counterclockwise direction around the stereocenter.

Uses

Used in Organic Chemistry:
[1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is used as a key intermediate for the synthesis of various organic compounds due to its unique structure and reactivity.
Used in Pharmaceutical Industry:
[1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is used as a building block for the development of novel pharmaceuticals, potentially targeting specific biological pathways or receptors due to its distinctive chemical properties.
Used in Perfumery:
[1R-(1alpha,3alpha,5alpha)]-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-ol is used as a fragrance ingredient in the perfumery industry, leveraging its unique scent profile and potential for creating complex and long-lasting fragrances.

Upstream product

• 17004-05-6 3-amino-β-pinene 
• 80-56-8 Pinene 
• 515-00-4 myrtenol 
• 58434-29-0 myrtenyl hydroperoxide 
• 22321-84-2 pinocarveyl hydroperoxide 
• 22321-84-2 trans-pinocarveyl hydroperoxide 
• 1686-14-2 α-pinene epoxide 
• 177698-19-0 Beta-pinene 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 25488-94-2 5,7,7-trimethyl-3-oxa-tricyclo[4.1.1.0^2,4]octane 
• 50-00-0 formaldehyd 
• 34413-88-2 pinocarvone 
• 18172-67-3 beta-pinene 

Downstream Products

• 38086-92-9 (4Z)-2,7-Dimethyl-2,4,6-octatriene 
• 99-48-9 (4R,6R)-carveol 
• 28385-58-2 3,6-dimethyl-2-methylene-hept-5-enal 
• 28385-56-0 (R)-7-methyl-3-methylene-octa-1,6-dien-4-ol 
• 18172-67-3 (?)-β-pinene 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 

Relevant articles and documents

Synthesis and oxidative transformations of new chiral pinane-type γ-ketothiols: Stereochemical features of reactions

Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)2 catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed.

Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst

Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.

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.