1004-58-6

Basic information

• Product Name: 1,4-Dioxaspiro[4.5]decane-6-ene
• Synonyms: 1,4-Dioxaspiro[4.5]dec-6-ene;1,4-Dioxaspiro[4.5]decane-6-ene;3,3-(Ethylenebisoxy)cyclohexene;Spiro[1,3-dioxolane-2,1'-[2]cyclohexene];1,4-Dioxaspiro[4.5]dec-6-en
• CAS NO: 1004-58-6
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.18
• Mol File: 1004-58-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 72-73 °C(Press: 12 Torr)
• Appearance: /
• Density: 1.053 g/cm3
• CAS DataBase Reference: 1,4-Dioxaspiro[4.5]decane-6-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dioxaspiro[4.5]decane-6-ene(1004-58-6)
• EPA Substance Registry System: 1,4-Dioxaspiro[4.5]decane-6-ene(1004-58-6)

Safety Data

• Hazardous Substances Data: 1004-58-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 48, p. 1449, 1992 DOI: 10.1016/S0040-4020(01)92233-1

Upstream product

• 1728-15-0 (R,S)-6-bromo-1,4-dioxaspiro<4.5>decane 
• 75-21-8 oxirane 
• 930-68-7 cyclohexenone 
• 108-94-1 cyclohexanone 
• 822-87-7 2-Chlorocyclohexanone 
• 107-21-1 ethylene glycol 
• 110-83-8 cyclohexene 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 
• 6954-16-1 (R,S)-6-chloro-1,4-dioxaspiro<4.5>decane 

Downstream Products

• 930-68-7 cyclohexenone 
• 64847-85-4 3-ethyl cyclohexanone 
• 22461-89-8 (R)-3-ethylcyclohexanone 
• 22461-89-8 3-ethylcyclohexanone 
• 20795-53-3 3-phenylcyclohexanone 
• 19770-37-7 3,3-ethylenedioxycyclohehene oxide 
• 77970-17-3 3-nitrocyclohex-2-ene-1-one 
• 119728-97-1 7-Formyl-1,4-dioxaspiro<4.4>non-6-ene 
• 122902-09-4 3-(2,3,4,5,6-Pentafluorophenyl)cyclohexanone 
• 132746-89-5 (+)-(R)-4-hydroxycyclohex-2-enone 
• 38693-58-2 1-ethynyl-cyclohex-2-en-1-ol 
• 765-87-7 cyclohexane-1,2-dione 
• 143208-81-5 trans-N-benzyl-5-benzenesulfonyl-7-n-butyl-8-benzyloxy-1-azaspiro<5.5>undecan-2-one 
• 143208-81-5 trans-N-benzyl-5-benzenesulfonyl-7-n-butyl-8-benzyloxy-1-azaspiro<5.5>undecan-2-one 

Relevant articles and documents

Facile Procedure for Acetalization Using Diols, Alkoxysilane and a Catalytic Amount of Trimethylsilyl Trifluoromethanesulfonate

In the presence of sec- or tert-alkoxysilane and a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf), carbonyl compounds react with various diols to give acetals in high yields.

Cadmium iodide catalyzed and efficient synthesis of acetals under microwave irradiations

A new selective method of acetalization of aldehydes and ketones with 1,2-diols, 1,3-diols or alcohols mediated by cadmium iodide under microwave irradiation is achieved in excellent yields.

Polyaniline-Supported Sulfuric Acid Salt as a Powerful Catalyst for the Protection and Deprotection of Carbonyl Compounds

Structurally different carbonyl compounds were converted into their corresponding cyclic acetals using polyaniline-sulfate salt as catalyst in dry toluene in excellent yield. In turn, useful deacetalization in aqueous medium was demonstrated. Chemoselective protection of carbonyl compounds was also demonstrated. The advantages of the polyaniline-sulfate salt are ease of preparation and handling, stability, reusability and activity.

Auxiliary controlled singlet-oxygen ene reactions of cyclohexenes

The photooxygenation of homochiral cyclohexene ketals, which are easily available from 2-cyclohexenone and l-tartrates, affords hydroperoxides and after reduction the corresponding allylic alcohols in good yields and high regioselectivities. This can be rationalized by electronic repulsions in a perepoxide intermediate and provides evidence for unfavorable 1,3 diaxial interactions with a dioxolane oxygen atom. Only low stereoselectivities were observed, due to the flexibility of the cyclohexene ring. However, the diastereomers could be separated and after cleavage of the auxiliary, 4-hydroxy-2-cyclohexen-1-one was isolated in enantiomerically pure form, which can serve as a building block for natural product synthesis.

Convenient preparation of cyclic acetals, using diols, TMS-source, and a catalytic amount of TMSOTf

With use of diol, alkoxysilane, and a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf), carbonyl compounds are converted to acetals in good yields under mild conditions. This procedure, which was carried out without synthesizing the silylated diols, is a more convenient adaptation of Noyori's method. This acetalization applies to not only simple but also conjugated carbonyl compounds. Moreover, various TMS compounds, including solid supported compounds, are effective for this method instead of alkoxylsilane.