16240-40-7

Basic information

• Product Name: 1-methyl-9-oxabicyclo[6.1.0]nonane
• Synonyms: 1-Methyl-cis-1,2-epoxycyclooctane
• CAS NO: 16240-40-7
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.2227
• Mol File: 16240-40-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 172.7°C at 760 mmHg
• Flash Point: 47.1°C
• Density: 0.957g/cm³
• Vapor Pressure: 1.76mmHg at 25°C
• Refractive Index: 1.473
• CAS DataBase Reference: 1-methyl-9-oxabicyclo[6.1.0]nonane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-9-oxabicyclo[6.1.0]nonane(16240-40-7)
• EPA Substance Registry System: 1-methyl-9-oxabicyclo[6.1.0]nonane(16240-40-7)

Safety Data

• Hazardous Substances Data: 16240-40-7(Hazardous Substances Data)

Usage

General Description

1-Methyl-9-oxabicyclo[6.1.0]nonane is a chemical compound that belongs to the class of bicyclic compounds. It is a colorless liquid with a molecular formula of C8H14O, and it has a distinct bicyclic structure with a unique 9-membered ring containing an oxygen atom. 1-Methyl-9-oxabicyclo[6.1.0]nonane is primarily used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. It is also known for its use as a reagent in chemical reactions, and its unique structure makes it an interesting target for chemical research and exploration of its potential applications in various fields.

Upstream product

• 4925-71-7 cis-1,2-epoxycyclooctane 
• 74-88-4 methyl iodide 
• 15840-64-9 1-methylcyclooctene 
• 933-11-9 methylcyclooctene 

Downstream Products

• 139313-68-1 (trans-2-hydroxy-2-methylcyclooctyl)diphenylphosphine oxide 

Relevant articles and documents

Enantioselective synthesis of epoxides by α-deprotonation - Electrophile trapping of achiral epoxides

Enantioselective α-deprotonation of achiral epoxides 1, 21, and 26 using organolithiums in the presence of (-)-sparteine 2 and subsequent electrophile trapping gives access to enantioenriched trisubstituted epoxides 9-17, 22, 23, 27 and 28 (in up to 86% ee).

Unusual temperature dependence in the cis/trans-oxetane formation discloses competitive syn versus anti attack for the Paterno-Buechi reaction of triplet-excited ketones with cis- and trans-cylooctenes. Conformational control of diastereoselectivity in the cyclization and cleavage of preoxetane diradicals

Toluene-d8 solutions of cis- and trans-cyclooctene (cis- and trans-1a) as well as (Z)- and (E)-1-methylcyclooctene (cis- and trans-1b) have been irradiated at temperatures between -95 and +110 °C in the presence of benzophenone (BP) to afford mixtures of the cis- and trans-configured oxetanes 2a,b and the regioisomeric 2b′. Correspondingly, benzoquinone (BQ) gave with cis- and trans-1a the cycloadducts cis- and trans-3a. The cis/trans diastereomeric ratios of the [2 + 2]-cycloadducts 2 and 3 display a strong temperature dependence; with cis- and trans-1a or cis-1b as starting materials, the diastereoselectivity of the oxetane formation is high at low temperature, under preservation of the initial cyclooctene configuration. With increasing temperature, the cis diastereoselectivity decreases continuously for the cis-cyclooctenes; in the case of the cis-1a, the diastereoselectivity is even switched to trans (cis/trans ca. 20:80) at very high temperatures. For the strained trans-1a, the trans-oxetanes are strongly preferred over the entire temperature range, with only minor leakage (up to 10%) to the cis-oxetanes at very high temperatures. Oxetane formation is accompanied by nonthermal trans-to-cis isomerization of the cyclooctene. The methyl-substituted trans-1b constitutes an exceptional substrate; it displays cis diastereoselectivity in the [2 + 2] photocycloaddition at low temperatures for both regioisomers 2b and 2b′, and the trans selectivity increases at moderate temperature (cis/trans = 4:96), to decrease again at high temperature, especially for the minor regioisomer 2b′. This complex temperature behavior of the cis/trans diastereoselectivity may be rationalized in terms of the triplet-diradical mechanism of the Paterno-Buechi reaction. We propose that the cyclooctene may be competitively attacked by the triplet-excited ketone from the higher (syn) or the less (anti) substituted side; such syn and anti trajectories have hitherto not been considered. To account for the unusual temperature behavior in the diastereoselectivity of the present [2 + 2] photocycloaddition, we suggest that temperature-dependent conformational changes of the resulting triplet preoxetane diradicals compete with their cyclization to the cis/trans-oxetane diastereomers and retro cleavage to the cis-cyclooctene.

Photocatalytic Oxygenation of Selected Cycloalkenes in Aqueous Solutions Induced by Water-Soluble Metal Porphyrin Complexes

Water-soluble manganese(III) as well as iron(III) porphyrinates are introduced as light-sensitive precursor compounds for the photocatalytic activation of dioxygen in aqueous solutions.It is shown that in the presence of α-pinene (4) and the further cycloalkenes 11-13 photocatalytic oxygenation reactions occur.The dependence of the selectivity of the oxygen transfer to the olefin on both the presence of water and the variation of the substrate-to-catalyst ratio is discussed.The catalyst may be conveniently separated from the substrates/products by using aqueous solvent systems. - Key Words: Photooxygenation / Dioxygen activation / Metallporphyrins / Epoxidation