1,4-Dioxaspiro(4.5)Decane-8-Carbonitrile
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1,4-Dioxaspiro(4.5)Decane-8-Carbonitrile

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1,4-Dioxaspiro(4.5)Decane-8-Carbonitrile (CAS# 69947-09-7) is used to prepare 1,2-dihydroquinolin-2-one and 1,2-dihydroquinoxalin-2-one derivatives as antibacterial agents. It is also used in the synthesis of heterocyclic sulfonamides as oral GlyT1 inhibitors.

Category
Others
Catalog number
BAT-008267
CAS number
69947-09-7
Molecular Formula
C9H13NO2
Molecular Weight
167.2
1,4-Dioxaspiro(4.5)Decane-8-Carbonitrile
IUPAC Name
1,4-dioxaspiro[4.5]decane-8-carbonitrile
Synonyms
4-Cyanocyclohexanone Ethylene Acetal; 8-Cyano-1,4-dioxaspiro[4.5]decane
Density
1.13 g/cm3
Boiling Point
308 °C
InChI
InChI=1S/C9H13NO2/c10-7-8-1-3-9(4-2-8)11-5-6-12-9/h8H,1-6H2
InChI Key
WZWQNWWFCHNJON-UHFFFAOYSA-N
Canonical SMILES
C1CC2(CCC1C#N)OCCO2
1. 2-[(E)-({3-[(E)-(2-Hy-droxy-benzyl-idene)amino-meth-yl]-1,4-dioxaspiro-[4.5]decan-2-yl}meth-yl)imino-meth-yl]phenol
Yan Jiang, Lili Wang, Jing Bian, Xiaoying Du, Xiaoqiang Sun Acta Crystallogr Sect E Struct Rep Online. 2012 Jul 1;68(Pt 7):o2296. doi: 10.1107/S1600536812029182. Epub 2012 Jun 30.
In the title compound, C(24)H(28)N(2)O(4), the dioxalane ring has an envelope conformation. The cyclo-hexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 72.5 (3)°. The mol-ecular conformation is stabilized by two intra-molecular O-H⋯N hydrogen-bonding inter-actions with an S(6) graph-set motif. The crystal structure is stabilized by van der Waals inter-actions.
2. (6R*,10R*)-Dimethyl 1,4-dioxaspiro-[4.5]decane-6,10-dicarboxyl-ate
Amita Jahangiri, Ola F Wendt, Daniel Strand Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 1;69(Pt 2):o265. doi: 10.1107/S160053681300161X. Epub 2013 Jan 19.
The title compound, C(12)H(18)O(6), is in the usual chair conformation with the two ester functions in a 1,3-trans orientation. With a value of 1.439 (2) Å, the pseudo-axial C-O bond of the 1,3-dioxolane ring is slightly longer than the corresponding equatorial C-O bond of 1.424 (3) Å. The O-C-O angle of the dioxolane ring is 106.25 (17)°.
3. 6-Benzyl-3-(1,4-dioxaspiro-[4.5]decan-2-yl)-8,8-dimethyl-1-oxa-2,6-diaza-spiro-[4.4]non-2-ene-7,9-dione
Yaser Bathich, Zurina Shaameri, Ahmad Sazali Hamzah, Ching Kheng Quah, Hoong-Kun Fun Acta Crystallogr Sect E Struct Rep Online. 2009 Oct 31;65(Pt 11):o2941-2. doi: 10.1107/S1600536809044675.
In the title compound, C(23)H(28)N(2)O(5), the 4,5-dihydro-isoxazole ring adopts a slight envelope conformation and the dioxolane ring is in a twisted conformation. The mol-ecular structure, in the vicinity of the benzyl group, may be influenced by an intra-molecular C-H⋯O hydrogen bond which generates an S(7) ring motif. In the crystal structure, mol-ecules are linked via weak inter-molecular C-H⋯O hydrogen bonds, forming extended chains along the b axis. Further stabilization is provided by weak C-H⋯π inter-actions.
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