77745-32-5

Basic information

• Product Name: 8-Oxabicyclo[3.2.1]octan-3-one
• Synonyms: 8-Oxabicyclo[3.2.1]octan-3-one;8-Oxabicyclo[3.2.1]octane-3-one
• CAS NO: 77745-32-5
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.16
• Mol File: 77745-32-5.mol

Chemical Properties

• Melting Point: 36 °C
• Boiling Point: 35 °C(Press: 0.001 Torr)
• Appearance: /
• Density: 1.141±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 8-Oxabicyclo[3.2.1]octan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Oxabicyclo[3.2.1]octan-3-one(77745-32-5)
• EPA Substance Registry System: 8-Oxabicyclo[3.2.1]octan-3-one(77745-32-5)

Safety Data

• Hazardous Substances Data: 77745-32-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Oxabicyclo[3.2.1]octan-3-one is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicines. Its unique structure allows for the creation of complex organic compounds that can address specific medical needs.
Used in Agrochemical Industry:
In the agrochemical sector, 8-Oxabicyclo[3.2.1]octan-3-one is utilized as a chemical building block for the production of agrochemicals. Its reactivity and structural properties enable the synthesis of compounds that can be used in pest control and crop protection, thereby supporting agricultural productivity.
Used in Fragrance Industry:
8-Oxabicyclo[3.2.1]octan-3-one is employed as a component in the creation of fragrances, where its distinctive odor and chemical properties are harnessed to produce a variety of scent profiles for use in perfumes, cosmetics, and other scented products.
Used in Asymmetric Synthesis:
8-Oxabicyclo[3.2.1]octan-3-one is used as a chiral auxiliary in asymmetric synthesis, a technique crucial for producing enantiomerically pure compounds. Its application in this field is significant for the development of more efficient and selective synthetic routes, leading to advancements in organic chemistry and the production of high-value compounds.
Used in the Synthesis of Natural Products:
8-Oxabicyclo[3.2.1]octan-3-one is also used in the synthesis of natural products, where its unique reactivity and structural features facilitate the production of complex organic molecules found in nature. This application is particularly important in the fields of biochemistry and pharmacology, where natural products often serve as lead compounds for drug discovery.

Upstream product

• 110-00-9 furan 
• 22612-89-1 1,1,3,3-tetrabromoacetone 
• 40458-77-3 8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 40458-77-3 meso-8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 124781-83-5 2-<2-(Phenylseleno)ethyl>-2,3-dihydropyran-4-one 
• 58986-98-4 2,2,4-Tribromo-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 
• 835632-81-0 3-((1R,2S,5R)-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-2-yl)oxazolidin-2-one 
• 835632-92-3 3-((1R,2S,5S)-3-Oxo-8-oxa-bicyclo[3.2.1]oct-2-yl)-oxazolidin-2-one 

Downstream Products

• 343963-51-9 (1R,3R,5S)-8-oxabicyclo[3.2.1]octan-3-ol 
• 1391759-31-1 8-oxabicyclo[3.2.1]octan-3-yl 2-phenylacetate 
• 73774-66-0 (+/-) methyl 3β-benzoyloxy-8-oxabicyclo<3.2.1>octane-2β-carboxylate 
• 73774-66-0 (+/-) methyl 3α-benzoyloxy-8-oxabicyclo<3.2.1>octane-2α-carboxylate 
• 73774-66-0 (+/-) methyl 3α-benzoyloxy-8-oxabicyclo<3.2.1>octane-2β-carboxylate 
• 73774-66-0 (+/-) methyl 3β-benzoyloxy-8-oxabicyclo<3.2.1>octane-2α-carboxylate 

Relevant articles and documents

Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna

(-)-Hyoscyamine, the enantiomerically pure form of atropine, and its derivative scopolamine are tropane alkaloids that are extensively used in medicine. Hyoscyamine 6β-hydroxylase (H6H, EC 1.14.11.11), a monomeric α-ketoglutarate dependent dioxygenase, converts (-)-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. In this study, H6H of Atropa belladonna (AbH6H) was cloned, heterologously expressed in Escherichia coli, purified and characterized. The catalytic efficiency of AbH6H, especially for the second oxidation, was found to be low, and this may be one of the reasons why Atropa belladonna produces less scopolamine than other species in the same family. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, was shown not to be an obligatory intermediate in the biosynthesis of scopolamine using purified AbH6H with an in vitro 18O labeling experiment. Moreover, the nitrogen atom in the tropane ring of (-)-hyoscyamine was found to play an important role in substrate recognition.

Chiral lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides

A chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reaction of allenamide-derived nitrogen-stabilized chiral oxyallyl cations is described here. The use of bisoxazoline ligand and CuOTf2 provides high enantioselectivity, especially with [SbF6]- as the counteranion. Copyright

A Lewis acid catalyzed intramolecular [4+3] cycloaddition route to polycyclic systems that contain a seven-membered ring

(Chemical equation presented). Two simple steps, including a new intramolecular [4+3] cycloaddition, are required for the preparation of polycycles that contain a seven-membered ring from 2-methyleneaziridines (see scheme). The diene component is introduc

Synthesis of 8-oxa analogues of norcocaine endowed with interesting cocaine-like activity

In order to further explore the importance of cocaine's bridge nitrogen atom in binding to the dopamine transporter (DAT), we have synthesized the previously known racemic 8-oxa-norcocaines 3-6 in which the nitrogen atom has been replaced by oxygen. Additionally, to avoid incorrect interpretations of biological data that may stem from the use of racemic materials, several of these analogues were synthesized and tested in non-racemic form. (-)-8-Oxa- norcocaine (3) was found to bind to the cocaine recognition site and to inhibit the dopamine transporter with potencies only about 8-fold and 4- fold, respectively, less than those of norcocaine (2). (-)-8-Oxa- pseudonorcocaine (4) as well as (+)-8-oxa-norcocaine (3) were found to be comparable in activity to (-)-oxa-norcocaine. These pharmacological findings support our earlier suggestion that cocaine is likely to bind in its neutral form to the DAT.

ETHER DERIVATIVES HAVING 5-LIPOXYGENASE INHIBITORY ACTIVITY

The invention concerns ether derivatives of the formula I Q1?X?Ar?Q2 wherein Q1 is an optionally substituted 9-, 10- or 11-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur; X is oxy, thio, sulphinyl or sulphonyl; Ar is optionally substituted phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl, thiazolediyl, oxazoiediyl, thiadiazoiediyl or oxadiazolediyl; and Q2 is selected from the groups of the formulae II and III: wherein R1 is hydrogen, (2-5C)alkanoyl or optionally substituted benzoyl; R2 is (l-4C)alkyl; and R3 is hydrogen or (l-4C)alkyl; or R2 and R3 are linked to form a methylene, vinylene, ethylene or trimethylene group; or a pharmaceutically-acceptable salt thereof; processes for their preparation; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.

The Demjanov and Tiffeneau-Demjanov one-carbon ring enlargements of 2-aminomethyl-7-oxabicyclo[2.2.1]heptane derivatives. The stereo- and regioselective additions of 8-oxabicyclo [3.2.1]oct-6-en-2-one to soft electrophiles

Nitrosation of 7-oxabicyclo[2.2.1]hept-5-en-2-exo-ylmethyl amine (20) gave 7-oxabicydo[2.2.1]hept-5-en-2-exo-methanol (22) whereas 7-oxabicyclo[2.2.1]hept-5-en-2-endo-ylmethylamine (21) afforded a 1:1 mixture of 7-oxabicydo[3.2.1]oct-6-en-2-ols (23) and 8-oxabicydo[3.2.1]oct-3-en-2-ols (24). Nitrosations of 2-exo- (28) and 2-endo-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ol (29) gave mixtures of 8-oxabicydo[3.2.1]oct-6-en-2-one (25) and 8-oxabicydo[3.2.1]oct-6-en-3-one (37). The preference for the C(3) methylene group migration giving 25 was the best (12:1) in the case of the 2-endo-aminomethyl alcohol 29. Compared with the nitrosations of bicydo[2.2.1]heptane analogues, the 7-oxa bridge in 28 and 29 enhances the preference for the C(3) methylene group migration vs. the C(1) methine group migration. The Tiffeneau-Demjanov one-carbon ring enlargement reactions of 2-exo-aminomethyl-7-oxabicyclo[2.2.1]hepta-2-endo-ol (30). 2-exo-aminomethyl-5-chloro (32) and 2-exo-aminomethyl-6-chloro-7-oxabicyclo[2.2.1]hept-5-en-endo-ol (33) are also reported. Under kinetically controlled conditions, 8-oxabicydo[3.2.1]oct-6-en-2-one (25) adds to electrophiles EX=PhSeCl, PhSeBr. 2,4-(NO)2C6H3SCl with high stereo- and regioselectivity giving the corresponding 8-oxabicyclo [3.2.1]-octan-2-ones where E substitutes the exo position of C(6) and X the exo position of C(7).

Enantioselective deprotonation of 8-oxabicyclo[3.2.1]octan-3-one systems using homochiral lithium amide bases

The asymmetric transformation of oxabicyclic ketones 6 and 7 into non-racemic enol silanes 12 (88% ee) and 10 (85% ee), respectively, was achieved using the homochiral lithium amide base 4. Conversion of 10 into a known key intermediate 15 for C-nucleosid

CNS-agents: Synthesis and properties of 3-anilino-8-oxatropanes

Reaction of the 8-oxabicyclooctenone and -octanone derivatives 3 and 4 with aniline and metal hydrides yields the 3α-isomers of the aniline derivatives 7 and 8, preferably. The configuration can be determined by NMR-spectroscopy and by cyclization to the

A Route to Linear, Bridged, or Spiro Polycyclic Compounds: Sequential Use of the Intermolecular Diels-Alder Reaction and Radical Cyclization

The intermolecular Diels-Alder reaction in which either the diene or the dienophile carries a suitably located homolyzable substituent, such as a phenylseleno group, represents a convenient method for assambly of compounds that can undergo radical cycliza