2205-98-3

Basic information

• Product Name: Spiro[2.5]octan-4-one
• Synonyms: Spiro[2.5]octan-4-one
• CAS NO: 2205-98-3
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.18028
• Mol File: 2205-98-3.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Spiro[2.5]octan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[2.5]octan-4-one(2205-98-3)
• EPA Substance Registry System: Spiro[2.5]octan-4-one(2205-98-3)

Safety Data

• Hazardous Substances Data: 2205-98-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 5501, 1984 DOI: 10.1016/S0040-4039(01)81610-5

Upstream product

• 70775-39-2 dimethylsulfoxonium methylide 
• 822-87-7 2-Chlorocyclohexanone 
• 72761-65-0 Spiro<2.5>dec-4-en-4-yl-trifluormethansulfonat 
• 185-65-9 spiro[2.5]octane 
• 2402-57-5 2-(2-chloroethyl)cyclohexanone 
• 78293-98-8 4-spiro<2,5>octanone oxime 
• 106-93-4 ethylene dibromide 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 935-36-4 2,2-Bis-brommethyl-cyclohexan-1-on 
• 143618-68-2 Oxo-phenyl-acetic acid spiro[2.5]oct-4-yl ester 
• 25059-70-5 2-chloroethyl dimethyl sulfonium iodide 
• 108-94-1 cyclohexanone 
• 3301-81-3 spiro<2.5>octan-4-ol 
• 1059-49-0 2,2-Bis-tosyloxymethyl-cyclohexan-1-on 

Downstream Products

• 110129-39-0 5-(4-Methoxy-benzyl)-spiro[2.5]octan-4-one 
• 110128-53-5 (4R,5R)-5-(4-Methoxy-benzyl)-spiro[2.5]octan-4-ol 
• 110128-53-5 cis-5-(4-methoxybenzyl)-spiro<5,2>-octan-4-ol 
• 52315-48-7 2-<2-(1'-Cyclohexenylethyl)>-spiro<2.5>octan 
• 4423-94-3 2-ethylcyclohexanone 

Relevant articles and documents

Piperidine trapping of conformationally restricted cyclopropylcarbenes

Conformationally restricted cyclopropylcarbenes were formed by photolysis (300+436 nm) of the corresponding oxadiazolines, and trapped with piperidine.

The reaction of dimethyloxosulphonium methylide with α-halocarbonyl compounds: a new synthesis of cyclopropanes

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RESIST COMPOSITION, METHOD OF FORMING RESIST PATTERN, POLYMERIC COMPOUND, AND COMPOUND

A resist composition including a resin component having a structural unit derived form a compound represented by formula (a0-1) (in the formula, W represents a polymerizable group-containing group; Ra01 is a group which is bonded to Ra03 to form an aliphatic cyclic group, or bonded to Ra04 to form an aliphatic cyclic group; Ra02 represents a hydrocarbon group which may have a substituent; Ra03 is a hydrogen atom or a monovalent organic group in the case where Ra01 is not bonded thereto; Ra04 is a hydrogen atom or a monovalent organic group in the case where Ra01 is not bonded thereto; and Ra05 to Ra07 each independently represents a hydrogen atom or a monovalent organic group).

Combined effects on selectivity in Fe-catalyzed methylene oxidation

Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.

Oxyfunctionalization of non-natural targets by dioxiranes. 5. Selective oxidation of hydrocarbons bearing cyclopropyl moieties

The powerful methyl(trifluoromethyl)dioxirane (lb) was employed to achieve the direct oxyfunctionalization of 2,4-didehydroadamantane (5), spiro[cyclopropane-1,2′-adamantane] (9), spiro[2.5]-octane (17), and bicyclo[6.1.0]nonane (19). The results are compared with those attained in the analogous oxidation of two alkylcyclopropanes, i.e., n-butylcyclopropane (11) and (3-methyl-butyl)-cyclopropane (14). The product distributions observed for 11 and 14 show that cyclopropyl activation of α-C-H bonds largely prevails when no tertiary C-H are present in the open chain in the tether; however, in the oxyfunctionalixation of 14 cyclopropyl activation competes only mildly with hydroxylation at the tertiary C-H. The application of dioxirane 1b to polycyclic alkanes possessing a sufficiently rigid framework (such as 5 and 9) demonstrates the relevance of relative orientation of the cyclopropane moiety with respect to the proximal C-H undergoing oxidation. At one extreme, as observed in the oxidation of rigid spiro compound 9, even bridgehead tertiary C-H's become deactivated by the proximal cyclopropyl moiety laying in the unfavorable eclipsed (perpendicular) orientation; at the other end, a cyclopropane moiety constrained in a favorable bisected orientation (as for didehydroadamantane 5) can activate an α methylene CH2 to compete effectively with dioxirane O-insertion into tertiary C-H bonds. Comparison with literature reports describing similar oxidations by dimethyldioxirane (1a) demonstrate that methyl(trifluoromethyl)dioxirane (1b) presents similar selectivity and remarkably superior reactivity.